Events in Winter Haven

Lorcana - Core Constructed

Take part in a Lorcana Core Constructed tournament with a $10 buy in. Matches are played in 50 minute Swiss rounds, best two of three, with the total number of rounds based on turnout and capped at three. Prizes include one booster pack for each match win, plus a pack for anyone who finishes without a match win. The top four receive promo cards, and two additional promos will be awarded by a roll of a big d20.

Trivia with Ron @ Raise the Bar and Grill

This event features three ten-question trivia games, with prizes awarded after each one. Attendees should plan to purchase food and drinks and bring a pen or pencil for writing answers. Bring your best brainpower for a chance to leave a winner.

Las Rosas Colombian Cuisine Pop-Up

Enjoy Colombian American Fusion food and street fare as they serve the city of Lakeland.

AARP Smart Driver™: Winter Haven Senior Center

An AARP Smart Driver course takes place at the Winter Haven Senior Adult Center. Participants must attend both sessions and should either pay online in advance or bring a check made payable to AARP. The fee is $20 for AARP members and $25 for nonmembers. Please remember to bring a driver’s license.

Kid's Eat FREE

This promotion features complimentary meals for children when an adult meal is purchased. A happy hour is also available.

Yikes! What's Happening to My Body? BOYS EDITION

An informative session for ages 9 to 12 that explores the bodily, cognitive, and emotional changes that come with the transition to adolescence. The program focuses on what children can expect as they get closer to their teen years.

Main Character Energy: Diva Night

Enjoy a painting and wine party! You can create your own long-lasting, all-natural scented soy candle before you paint. This event is open to painters 15 years or older, but those under 18 must be accompanied by a paid adult. Instruction begins promptly at the start time. You can enjoy a drink from the bars selection of wine, beer, or non-alcoholic beverages, and you may also bring your own snacks.

Polk State Student Art Exhibit Reception

Polk State is presenting the annual reception for its Student Art Exhibition at the Winter Haven Fine Arts Gallery. Admission is free. The exhibit remains on display and is open to the public.

Pokemon League Challenge - April 2026

Take part in a monthly Pokemon League Challenge featuring Standard Format play with best of one rounds. Registration is required by phone at 863-324-1323, and participation is limited to 16 players, so securing a spot in advance is necessary. Expect three to four rounds based on turnout. Entry is $5. Bring a completed decklist to check-in that includes your first and last name, Pokemon ID number, date of birth, and the exact counts and versions of every card in your deck. Matches begin promptly, and players who arrive late or do not submit a completed decklist before the first round will not be able to participate. Prize support includes one prize pack for each match win, an extra pack for the top four finishers, and a pack for every participant.

Tribute to Aerosmith and more

At The Ritz Theatre, a double bill salutes the music of Aerosmith and Loverboy. Aerosmith Rocks! delivers the band’s arena-sized punch with soaring vocals, fiery guitar work, and stagecraft that recalls Steven Tyler’s signature moves. Expect classics like Walk This Way, Dream On, and Sweet Emotion alongside deeper tracks, all played with tight precision. Get Lucky follows with a lively tribute to Loverboy, rolling through Working for the Weekend, The Kid Is Hot Tonight, and more signature hits. Sharp harmonies, propulsive rhythms, and an unmistakable 80s spark keep the energy high from start to finish.

Aerosmith Rocks! and more

Aerosmith Rocks! channels the band’s bad-boy swagger with gritty attitude, soaring vocals, scorching guitar work, and the unmistakable frontman strut that recalls a full throttle Aerosmith concert. Get Lucky follows with a high energy salute to Loverboy, serving up favorites like Working for the Weekend and The Kid Is Hot Tonight while capturing the upbeat spirit of the 80s. Built for rock fans of all ages, it is pure feel good, fun loving rock and roll.

Polk State Music Spring Choir Concert

Polk State Music presents a Spring Choir Concert at the Polk State Winter Haven Fine Arts Theatre. General admission costs $10. Students with school IDs and Polk State faculty and staff with College IDs can attend for free.

Trivia Night

Trivia night offers a friendly question-and-answer challenge.

OneBlood Blood Drive

Give blood at the OneBlood drive hosted at Oak Ridge Funeral Care - Winter Haven. Donors receive a $20 eGift card, an umbrella, and a wellness checkup that includes blood pressure, pulse, temperature, iron, and cholesterol screening. Appointments are encouraged to reserve a spot. A valid ID is required. The donor offer is limited to one per donor per donation, has no cash value, is not transferable, and items may vary while supplies last.

Ribbon Cutting: Miller's Central Air

Celebrate the grand opening of Miller’s Central Air’s second location in Winter Haven. For more than three decades, the company has delivered expert air conditioning, heating, and HVAC services. Drawing on deep experience with Florida’s climate, coastal environments, seasonal humidity, and intense heat, the team offers practical insight into how local HVAC systems perform, age, and adapt to environmental changes. RSVP to Lynn by email.

Taco Tuesday

Three tacos served with fries or chips and salsa are available for $8.99. A happy hour is offered as well.

Free Educational Seminar on Estate Planning

Attend a complimentary event hosted by the National Association of Family Services and discover how to help your family leave a legacy. Learn how to organize your affairs and secure your estate and financial needs.

Wine Tasting

Join in for an evening where you can enjoy some wines with a charcuterie board. Its a chance to unwind, taste new flavors, and enjoy great company. Do not miss out on this experience!

Neon Mountain Sunset: Blacklight

This event is for ages 15 and up. You can create your own long-lasting, all-natural scented soy candle before you paint. If you choose to make a candle, please arrive no later than 30 minutes prior to the event. Enjoy a drink from the bar’s selection of wine, beer, or non-alcoholic beverages. You may also bring your own snacks.

Free Bingo

Enjoy a free bingo night at Bowen Yard in Downtown Winter Haven. Share the fun with friends, enjoy food from five restaurants, and play for prizes.

Magic - Mid-Week Pauper

Take part in a Magic Pauper tournament with a $10 entry fee. Matches are played as best of three in 50 minute Swiss rounds. Earn one prize ticket for each match win, plus an extra ticket for finishing in the top four, and redeem tickets for different booster packs. First place receives a foil promo pack, and additional promo packs will be awarded at random.

Blueberry Upick Today!

Harvest fresh blueberries at a u-pick event. Berries are priced at $5 per pound. Buckets are available for picking, and bags are provided for taking your blueberries home.

Jukebox Bingo

Jukebox Bingo offers a chance to play bingo.

AYCE Boneless Wings

All-you-can-eat boneless wings are available, with a happy hour also offered.

Starlit Crescent - Book Club

Enjoy a painting event for ages 15 and up. An instructor will guide you in creating your own art. Drinks including wine and beer are available for purchase, and you can bring your own snacks. It is required to arrive by the designated start time or 30 minutes early if making a candle. If you want to sit with friends, all guests must enter the same group name when registering. You can also create your own scented soy candle before you paint, just look for the DIY CANDLE add-on during registration.

Winter Haven Middle School Classic

This middle school classic takes place in Winter Haven, Florida and is featured on MileSplit with an official meet page.

Ribbon Cutting: Winter Haven Recreation and Cultural Center

A ribbon cutting with the City Commission will mark the official opening of the new Winter Haven Recreation and Cultural Center. An open house with tours follows, providing a chance to see the facility. This $21 million investment, shaped through extensive community input and collaboration, represents a meaningful milestone for the community.

Two-Headed Giant Commander B-I-N-G-O

Players team up with a friend for a laid-back Two-Headed Giant Commander event with a B-I-N-G-O twist. Each participant receives a bingo card on arrival. Players form groups of three or more and aim to complete the tasks listed on their cards. Finishing a row earns a promo, and filling the entire card awards a promo pack. Entry is the purchase of a booster pack of your choice. Participation promos are available for all players. Two-Headed Giant Commander rules are in effect.

Nitro Bingo

Nitro Bingo turns a familiar pastime into a high-energy night with flashing light effects, lively music, and a friendly, social vibe. It suits groups, a friends’ night out, or anyone seeking an exciting midweek break. Look for a total prize pool of $1,350 and an atmosphere that keeps the energy high from start to finish.

Everyday Magic w/ Alex.

Returning by popular demand, this class with Alex focuses on practical ways to weave magical practice into daily life, helping connect the inner self with the outer world. After more than a year away from Moon Dreamz, Alex brings back a session that works well for newcomers and for anyone seeking a refresher. The class is $20 per person. Before the session, Alex will be available for in-house readings, offering a chance to meet with him ahead of time.

Peace Train Karaoke

Peace Train Karaoke brings a karaoke night to Jessie's Lounge, where attendees can sing favorite tunes, move with the playlist, and choose from a fitting drink selection. Set in downtown Winter Haven, it is centered on stepping to the mic and sharing the music.

AYCE Bone-In Wings

Unlimited classic bone-in wings are offered, and a happy hour is available.

Sassy Henrietta

Enjoy a painting session to create your own version of Sassy Henrietta. This event is for ages 15 and up. You can purchase wine, beer, and non-alcoholic beverages. You may also bring your own snacks. Arrive 15–20 minutes early to check in and get settled. Instruction starts promptly on time.

First Friday Free Bites!

First Fridays get underway at Bowen Yard with complimentary samples from the restaurants at the venue. Stop by to taste a few bites and get a feel for the dining options available there.

First Friday

First Friday is a monthly evening in downtown Winter Haven filled with dining, drinks, and shopping. Visitors will find specials at local bars and restaurants, explore downtown businesses that stay open later for the occasion, and enjoy live music along with other entertainment at several locations. The festivities also feature the First Friday Car Show and the First Friday Night Market.

First Friday Market

The Winter Haven Night Market offers a family friendly evening with a car show, local vendors, and Zesty Bubbles serving dirty soda and dirty popcorn. Attendees can enjoy a welcoming atmosphere with eye catching cars and chances to browse and shop from local sellers.

Live & Loud

Live & Loud brings Polk County a monthly jolt of homegrown sound at the Historic Ritz Theatre. This series elevates rising artists and creatives from the local scene, offering a welcoming, inclusive setting where they can push boundaries, claim the stage, and make plenty of noise. This edition spotlights Lyche Camp from Tampa, Colorblind Dinosaurs from Mount Dora, and Defrauded from Tampa. Presented in partnership with Punk Kid Productions LLC.

Magic - Standard Showdown

This Magic Standard event features three Swiss rounds, each 50 minutes and played best of three. Earn one prize ticket for each match win, with an extra ticket awarded to players who finish in the top four. Tickets can be redeemed for assorted booster packs. First place receives a foil promo pack along with an additional promo card. Extra promo packs will also be distributed at random. The buy in is $10.

May First Friday - Sip & Glaze

Enjoy a relaxed, creative evening as AS Ceramics teams up with Union Taproom for a First Friday edition of Sip & Glaze. No experience is necessary. Each ticket includes a handmade ceramic incense burner crafted by local artist Austin Snedden, a full range of professional glazes with all the brushes and tools, and on-site guidance to help you customize your piece. After you finish glazing, the burner will be taken to the studio for kiln firing and will be available for pickup at a later time. All ages are welcome. Union Taproom in Winter Haven features a pour-your-own selection of craft beers, wines, and ciders that sets an easygoing atmosphere for making art. Tickets are $40 per person, and capacity is limited, so early purchase is encouraged.

Live and Loud

Live & Loud brings Polk County a monthly surge of underground sound and emerging talent in an inclusive, welcoming setting where up-and-coming artists push limits and take the spotlight. Each installment is built for discovering fresh bands from the region. This edition spotlights Defrauded, Lychee Camp, and Grim Gardener from Tampa, alongside Colorblind Dinosaurs from Mount Dora.

Conspiracy Theory Rocks La’s Midway!

Conspiracy Theory returns to La’s Midway Saloon with a high‑voltage set celebrating rock and pop across the decades. The show rolls through signature anthems and fan favorites by Journey, Led Zeppelin, Black Sabbath, Billy Idol, Poison, Tesla, Stone Temple Pilots, Aerosmith, Alice Cooper, Duran Duran, George Michael, Weezer, Korn, Godsmack, and more, creating a lively soundtrack for a full night at the saloon.

99 in the Shade @ Somewhere Sports Bar & Grill!

An evening of dancing unfolds at Somehwre Sports Bar and Grill, with food and drinks available and staff on hand throughout the night.

Blueberry Upick Today!

Enjoy a u-pick blueberry experience at the farm, with pricing at $5 per pound. Buckets are provided for picking and bags are available to take your berries home.

Fish Fry Friday

Enjoy fish and chips offered as a special, along with a happy hour.

You Name It!

A comedic performance spotlights Charlie, who presents herself as a woman of many trades, offering everything from medical help and tax fixes to ticket hookups. Whatever you need, she says you only have to name it. In truth, her friendly facade hides a skilled scammer.

Let’s Get LITerary

A candlelit meetup for creatives and readers invites attendees to bring the book they are currently reading to spark conversation, share recommendations, and connect with others who love to discover new stories. Capacity is limited to eight people, encouraging an intimate, relaxed atmosphere. Light bites and refreshments will be available.

David Jolly

Free Comic Book Day

This one day giveaway offers complimentary comics. Each person may choose up to five different issues from the designated free comic tables, and holds are not available.

Magic - Secrets of Strixhaven Draft League

This Magic draft league features three 55 minute rounds, each played best of three. Players earn one prize ticket for every match win and can redeem tickets for booster packs after each event. League scoring awards three points per event attended and one point per match win, with bonus prizes at 10 and 20 points. The buy-in is $25 per draft event.

Are You Ready To Get Twizted?

Caribbean Bay hosts a rock and roll celebration with a Twizted twist, bringing lively party energy and upbeat vibes.

Bobby James

Bobby James returns to Florida with a stop at Twisted Prop, performing songs from his current album Madison alongside covers that have influenced his music.

Blueberry Upick Today!

Pick your own blueberries at the farm. The price is $5 per pound. Buckets are supplied for picking, and bags are provided so you can take your berries home.

Cardboard Boat Race

Celebrate local lakes, rivers, and the underground drinking water supply at a community festival featuring a team cardboard boat race that spotlights creativity and problem solving from residents, businesses, community groups, and youth organizations. Teams craft a boat primarily from cardboard and duct tape, then send two pilots to paddle a course that begins on the beach, circles the ski jump, and returns to shore. Trophies and prizes are offered in two divisions, adult for ages 18 and up and youth for under 18, with special honors that include the Swift Dinghy Award for the fastest finish, the Gene Leedy Award for most creative design, and the Titanic Award for the most spectacular sinking. Family and friend teams are welcome and no official affiliation is required. A $25 entry fee and signed liability waiver are required to compete. Each team must field two pilots, while any number of additional helpers may assist with design and construction. Adults may help youth teams build, but both pilots must be under 18 to compete in the youth division. Space is limited to ten teams per age category and registration is first come, first served. Pilots must wear a Type 1, 2, or 3 personal flotation device. Teams are encouraged to bring their own PFDs, and a limited number may be available from event staff if requested in advance. Boats and paddles must be built by each team and made primarily of cardboard. Materials such as rubber, foam, inflatables, and wood may not be used to enhance buoyancy. Duct tape, glue, and contact cement are acceptable adhesives, but waterproof coatings on the underside of boats are not allowed, and motorized propulsion is prohibited. One week before the festival, each team receives a construction kit with four sheets of 4-by-8-foot cardboard, three rolls of duct tape, a ruler, a utility knife, and two pencils. Teams may purchase additional materials for building or decorating, and designs should avoid offensive, political, or inflammatory themes. Event staff may disqualify teams that break the rules, which can include forfeiting the entry fee and potential bans from future events.

Winter Haven Farmers Market

Explore a lively farmers market featuring farmers, food trucks, and local makers. Pick up fresh produce, handmade pasta, baked goods, meats and seafood, and a variety of plants while you browse the vendors.

7 Rivers Water Festival

The 7 Rivers Water Festival is a community celebration of shared water resources in the Polk County region, marking more than a decade of dedication to protecting them. Attendees can explore vendor booths, watch a cardboard boat race, and enjoy a performance by the Cypress Gardens Water Ski team. Presented in collaboration with the City of Winter Haven, Polk County, and the City of Lakeland, the festival promotes understanding, appreciation, and stewardship of lakes, rivers, and the underground drinking water supply.

Lounge Lyzrds at La's Midway Saloon - 5/2/26

After some time away, Lounge Lyzrds return to La's Midway Saloon in Lake Albert, ready to bring their Lyzrd-style party back to a familiar stage.

Annual Spring Tack Sale

Browse a seasonal tack sale with fill-a-bag specials and buy one, get one promotions on both new and used tack. Stock up while supporting feed and hay expenses, as all proceeds are dedicated to that purpose.

Watermelon Day

This annual celebration features free admission and a variety of watermelon themed activities.

31st Annual Heritage Day Festival

The 31st Annual Heritage Day Festival is a free community gathering that celebrates legacy, unity, and culture. Expect live entertainment, a colorful fashion showcase, a variety of food vendors, an auto show, and activities for children. Complimentary health screenings will be available, and the program features a tribute to historic churches in Polk County.

Bandit Market Summer Party

Back for its tenth edition, Bandit Market brings a sunny celebration of makers and finders. Explore vendors from across central Florida featuring vintage treasures, art, handcrafted wares, baked goods, and more. Vendor applications are open.

Mom's In Love with Sunflowers

Depot Walk: May the Arts Be With You — Lakeland Arts Association

Experience the next Depot Walk in the Depot Arts District with Lakeland Arts Association, a celebration of creativity that brings art, community, and imagination together. Wander through the district as resident artists open their studio doors for a closer look at their workspaces and connect with the creative community along the way.

Pro Late Models Round 3

The third round of Pro Late Model action at Auburndale Speedway hits the track for this season.

Spring Has Sprung

Paint Spring Has Sprung at a painting and wine party. Painters ages 15 and up are welcome to attend with a paid adult. Those making a candle should arrive 30 minutes early. Enjoy a selection of wine, beer, or non-alcoholic beverages from the bar. You may also bring your own snacks. Payment is required at the time of booking to reserve your seat. Located in High Pointe Plaza, behind Citizens Bank.

Yu-Gi-Oh - Blazing Dominion Premiere Event

Entry requires purchasing five or more Blazing Dominion Booster Packs. Play follows the Advanced format, and Blazing Dominion cards are legal. The event runs for three to four Swiss rounds, with matches decided in a best of three. Prize support includes OTS packs, additional Blazing Dominion Booster Packs, and special promo items for first place and for one randomly selected player.

Blueberry Upick Today!

Enjoy a u-pick blueberry experience at the farm. Pricing is $5 per pound, and buckets for picking along with take-home bags are provided.

Mother's Day Brunch

A brunch gathering dedicated to honoring mothers and the mother figures who enrich our lives. It offers a thoughtful occasion to express appreciation and gratitude for their care and support.

B.Haven Band

B.Haven Band will be performing.

Flowers for Mom

Enjoy a painting and wine party. With step-by-step guidance from experienced local artists, you can create a unique piece of art. You can also create your own scented soy candle before you paint if you arrive 30 minutes early. There is an additional charge for the candle option. This event is open to painters ages 15 and up with a paid adult. Those 18 and over are welcome to attend on their own. Guests can purchase wine, beer, or non-alcoholic beverages at the bar. You may also bring your own snacks.

Brunch on 1st

Experience a daytime hangout with a great vibe. Book your seat for Brunch on 1st, it promises to be fun!

Open Mic Night

Take the stage at Gram Parsons Derry Down for an acoustic-only open mic where performers of any age can share up to three songs. Sign in when you arrive to get on the list. Newcomers, seasoned players, singer-songwriters, and anyone working on their craft will find a welcoming, supportive setting. Audience members are welcome to attend and enjoy the music. Admission is free. Hosted by Jay Hill.

Lorcana - Infinity Constructed

This special Infinity Format event allows participants to use cards from any set with no restrictions. The competition runs as Swiss rounds played best of three. Prize support awards one booster pack for each match win, and players with no wins also receive a booster. Extra rewards go to the top four, and two additional prizes will be determined by a roll at the end. The buy-in is $10.

Trivia with Ron

Trivia with Ron at Raise the Bar and Grill features three games, each with ten questions. Prizes are awarded after every game, offering multiple chances to win. Bring money for food and drink, along with a pen or pencil and your brain. You could walk away a winner.

FREE Skin Cancer Screening

Winter Haven Women's Hospital is offering free skin cancer screenings in recognition of Melanoma Monday. The checks are quick and comfortable. Adults age 18 and older are eligible. Wear loose clothing to make the screening easier. Walk-ins are accepted as availability allows.

Empire StarScape - 3 Hour- Black Light

Enjoy a painting and wine party where you can create your own Empire StarScape. An instructor will guide you step by step. Painters ages 15 and up are welcome, and those ages 15-17 may attend with a paid adult. You can purchase wine, beer, or non-alcoholic drinks. You may also bring your own snacks. You can also make a scented soy candle before you paint, just arrive 30 minutes early.

Revenge of the Fifth

Hosted by Vicar Moore in Trinity Hall, this Revenge of the Fifth celebration includes cantina-style snacks, creative craft activities, and a screening of Star Wars: A New Hope. Costumes inspired by favorite characters are encouraged, and friends are welcome, all while marking 49 years of Star Wars.

Pokemon League - Standard

Take part in a weekly Pokemon gathering that centers on a Standard-format tournament with best-of-one Swiss rounds. Entry is $5. Players earn a prize pack for each match win, and the top four competitors receive an additional prize pack plus a booster pack. Collectors and casual players are welcome to spend time trading cards and enjoying casual games alongside the tournament.

Polk State College vs College of Central Florida

Tacos and Tequila: Cinco de Mayo

Enjoy a painting activity with step-by-step guidance from experienced local artists. Attendees can purchase wine, beer, and non-alcoholic drinks. Painters ages 15+ may attend with a paid adult. Optionally, you can create your own scented soy candle before you paint, but you should arrive 30 minutes early if you choose to make a candle.

Magic: Pauper

This Pauper format Magic event features three 50 minute Swiss rounds with best of three matches. Participants receive one prize ticket for each match win and an extra ticket for placing in the top four, and tickets can be exchanged for assorted booster packs. First place earns a foil promo pack, and additional promo packs are distributed at random. Entry is $10.

Blueberry Upick Today!

This u-pick blueberry event features fresh berries you can harvest yourself for $5 per pound. Buckets are provided for picking, and bags are available for taking your berries home.

Wellness Wednesday: Custom Quick Pour

Walk in and craft a personalized 10 ounce wooden wick candle. Select your preferred fragrance, then design it with botanicals and meaningful affirmations. Available only at FLAME.

2026 "She Knows Where She's Going" Luncheon

At Historic Ritz Theatre, Inc, the 2026 She Knows Where She's Going Luncheon honors four women whose dedication and contributions have benefited the Greater Winter Haven community. This luncheon offers a warm celebration of their service and local impact.

Peony Bouquet for Mother

Enjoy a painting and wine party. Painters ages 15 and up can join, and those under 18 must be accompanied by a paid adult. With the help of an instructor, you can create your own peony bouquet. You can also purchase wine, beer, and snacks at the bar. It is possible to create a scented soy candle before you begin painting, but you must arrive 30 minutes before the event to do so.

Magic - Secrets of Strixhaven Commander Bingo Party

Casual Commander play meets bingo with Secrets of Strixhaven themed twists. Each participant receives a bingo card at the start, then forms a group of three or more players to work on the tasks listed on the card during games. Finish any line to claim a promo, and complete the entire card to receive a promo pack. Participation promos are provided to all players. Entry requires purchasing a booster pack of your choice.

Nitro Bingo

Nitro Bingo amps up the classic game with flashing lights, energetic music, and a lively, social vibe suited to groups, a girls night, or anyone in the mood for high-energy fun. A prize pool of $1,350 raises the stakes and keeps the excitement going with every card.

Conversations in Behavioral Health: Building a Mindful Community

Mental health touches families, workplaces, classrooms, and neighborhoods across Polk County, yet important dialogue often begins only after a crisis. This summit was created to shift that pattern by fostering proactive, meaningful conversations. Now in its third year, it brings together professionals, community leaders, educators, healthcare providers, and residents who share a commitment to strengthening mental and behavioral health locally. The one day program features three keynote talks that blend insight with lived experience, eight breakout sessions focused on practical strategies, emerging topics, and community solutions, and a hub of local behavioral health organizations offering resources and support. Throughout the event, participants engage in open, honest discussions that build understanding, reduce stigma, and provide tools that can be used at home, at work, and in schools. Attendees leave with deeper knowledge, stronger connections, and a clearer path to creating healthier, more supportive environments across Polk County. It is designed for behavioral health and healthcare practitioners, educators and youth advocates, nonprofit and community leaders, law enforcement and first responders, employers and HR professionals, faith leaders and ministry teams, parents, caregivers, and community members who value mental wellness. Registration is free, although space is limited.

Peace Train Karaoke

Jessie's Lounge hosts Peace Train Karaoke, a sing-along night where participants can perform favorite songs, groove to a curated playlist, and enjoy a fitting drink selection. In downtown Winter Haven, it provides an opportunity to harmonize with others during a dedicated karaoke session.

Spring Stroll with Mom - Blacklight

Enjoy a painting session suitable for ages 15 and up. Painters aged 15+ may attend with a paid adult. You can purchase wine, beer, seltzer, cider and non-alcoholic drinks on site. You may also bring your own snacks. You can also create your own scented soy candle before you paint for an additional fee. Arrive early if you choose to make a candle. Please note that instruction begins promptly on time. If youd like to sit with friends, make sure to register under the same group name.

2nd Friday Night Meetup

This free event is open to all. All makes, models, and years are welcome to show off their rides.

Tribute to Pink Floyd

A celebration of Pink Floyd takes the stage at The Ritz, featuring music from Dark Side of the Moon, The Wall, A Momentary Lapse of Reason, and Wish You Were Here. Classic Rock Legacy leads the performance with a roster of award-winning musicians whose past collaborations include Sting and Godsmack. An immersive light and laser show accompanies the music.

Blueberry Upick Today!

Enjoy a pick-your-own blueberry outing at the farm. Pricing is $5 per pound. Buckets are supplied for harvesting, and bags are provided so you can carry your berries home.

Florida Pro Wrestling

Enjoy Pro Wrestling at its best!

Magic - Secrets of Strixhaven Draft League

Experience a Magic draft league centered on Secrets of Strixhaven. The event runs across three rounds of 55 minutes each, played best two out of three. Every match victory earns a prize ticket, which can be exchanged for a selection of booster packs at the end of the event. Participants receive three league points for attending and one point for each match win, with bonus rewards available at 10 and 20 league points. Entry for each draft is $25.

Mother’s Day Charcuterie Workshop

Mark Mother’s Day with a hands-on charcuterie workshop that highlights connection and creativity as participants build a custom board to share. It can serve as a thoughtful gift and a memorable activity, turning time together into something delicious to enjoy. The experience includes a 10 inch round wooden keepsake board, gold mini serving tongs, a cheese knife with a wooden handle, a Mother’s Day charm, premium cheeses and meats, mini jam, seasonal fruit, and a sweet treat. All supplies are provided, and tickets are non-refundable.

Pokemon: Chaos Rising Prerelease

Preregistration is required because space is limited. Reserve a spot by calling 863-324-1323 or registering in person. This sealed event uses a build and battle kit, with energy provided by the shop. Play consists of three Swiss rounds, each best of one. Prize support is one booster pack per match win, and any player with no wins receives one booster pack. The buy-in is $35.

Deep Well Project- Live! at Tipsy Hen

Deep Well Project performs live at Tipsy Hen, a venue that welcomes families in the heart of downtown Winter Haven. The spot features wings, a range of draft beers, and other eats to enjoy alongside the music.

Interest Meeting

Learn about Haven Hybrid Academy at an interest meeting held at Southside Baptist Church. The session covers what the academy offers and how the program is structured, and includes time for questions.

Almost There

Almost There brings an outdoor show to the parking lot at Somewhere Sports Bar in Winter Haven. The set spans rock, metal, alternative, pop, and classics, with the possibility of a few new songs requested by friends. Expect a lively night with drinks and live music.

Blueberry Upick Today!

Enjoy a hands-on blueberry picking experience. The price is $5 per pound. Buckets are available for picking, and take-home bags are provided.

The Highway 41

The Highway 41 Band, a country group from Central Florida, returns to Out-n-About Bar and Music Lounge for an evening of country music.

Winter Haven Saturday Markets

This event takes place in Winter Haven, Florida and is organized by Winter Haven Saturday Market.

A Mother's Heart

Pure Shores

Enjoy a guided painting session suitable for ages 15 and up, led by instructor Valentina. Guests can purchase wine, beer, or non-alcoholic beverages, and are welcome to bring their own snacks. Arrive early if youd like to make your own all-natural scented soy candle.

2026 AAU Tangerine Tango Grand Prix

The 2026 AAU Tangerine Tango Grand Prix will feature over 90 volleyball teams competing. Admission is charged per day, with weekend passes available. Spectators can watch from the upstairs viewing area, and are welcome to bring chairs as seating is limited. Enjoy vendors, food trucks, a food drive, giveaways and themed days. Wear Christmas attire on the first day and floral prints on the second.

Little Birdies

Every Saturday, the community is invited to a vibrant market featuring locally-grown produce, fresh pasta, baked goods, juices, meats, seafood, plants, and unique creations from local makers. This week, The Little Birdies will perform their Appalachian-style bluegrass.

Kundalini Rising

Evelyn presents Kundalini Rising, an immersive journey that moves from energizing Kundalini Yoga, to calming Yin Yoga with journaling, then into an ecstatic dance finale with DJ EvaNova. The experience is designed to awaken energy, encourage reflection, and invite freeform movement for a deeper connection to your inner current. Hosted at Buffy's Boutique in Winter Haven.

JSA PTA May Meeting

This is the last PTA meeting of the school year, held at Jewett School of the Arts in the cafeteria. Discussion will focus on the remaining events planned for the rest of the school year. Everyone is welcome to attend, and PTA members who cannot make it will receive an email recap.

Lorcana: Wilds Unknown Prerelease (Sealed)

This event marks the first Lorcana prerelease to use the new Prerelease Kits. It runs as a sealed deck tournament with three Swiss rounds, best of one, at 30 minutes per round. Prize support includes one booster pack for each match win, and any player without a match win still receives a pack. Additional boosters will be given out at random based on the roll of a big d20. Entry is $50.

Arabellas Pre-Show Dinner Special

Turn Tribute Tuesday into an Italian evening with a pre-show four-course dinner in Winter Haven. Begin with an antipasto such as burrata caprese, mozzarella in carrozza, or fiocchi al gorgonzola, followed by a fresh house salad. For the main course, choose from salmon with a honey dijon glaze, NY strip tagliata di manzo, fettuccini alfredo, house lasagna, or chicken or veal prepared piccata, parmigiana, or marsala style. A chef-selected dessert completes the meal. Vegetarian selections are available, and most allergies can be accommodated. Substitutions are not offered, and beverages, alcoholic drinks, and gratuity are not included.

Feeling Flawless: Diva Night

Enjoy a painting and wine party where you can create your own artwork. An experienced local artist will provide step-by-step instructions. This public event is open to those 15 years and older, but painters ages 15+ must attend with a paid adult. You can also make your own scented soy candle for an additional fee. You are welcome to purchase wine, beer, or non-alcoholic beverages at the bar. Feel free to bring your own snacks. Reservations and payment are required to reserve your seat.

1 Million Cups

A free, weekly gathering where local founders showcase their ventures and receive immediate feedback over coffee. Each session features two entrepreneurs delivering pitches and hearing reactions from the group.

Magic Commander Bingo

Magic Commander gets a bingo twist in this casual event. Participants receive a bingo card on arrival, then form groups of three or more to work through the tasks on their cards. Completing any line earns a promo, and filling the entire card earns a second promo. The buy-in is a booster pack purchase of your choice.

Red, White & NEW Trade Event

Promoted as the dealership’s biggest RV trade event of the year, this multi-day showcase focuses on high-value trade-ins and special pricing on new RVs, with payments advertised from $94/month*. The event features strong trade offers, a chance to win a new RV with no purchase necessary, savings of up to 40 percent on camp-ready essentials, and a complimentary cookout during the festivities.

A Cottage View

Enjoy a painting session to create "A Cottage View." Painters ages 15 and up are welcome to attend with a paid adult. You can also create your own scented soy candle before the painting session, please arrive 30 minutes early if you choose to make a candle. Enjoy a drink from the selection of wine, beer, or non-alcoholic beverages at the bar. You may also bring your own snacks.

Winter Haven VFW

The Summit Kings perform at Vfw Post 4289 with a mix of classic rock and energetic blues tailored for both dancing and listening.

Twizted Times Call For Twizted Measures

A lively evening built around music, a Cuban sandwich with a twist, and a cold brew by the lakeside. The atmosphere leans easygoing, pairing simple flavors with a soundtrack that keeps the good times rolling.

Riftbound

Riftbound - Nexus Nights features a 1v1 Constructed format with three 50 minute Swiss rounds played as best of three. Prize support includes one booster pack for each match win, a booster pack for anyone who finishes without a match win, and an extra pack for the top four. Entry is $10.

B.Haven Band

B.Haven Band will be performing.

Wicked Moonlight

Spring Short-Film Festival (Friday) HSA Film Theatre

The Motion Picture Arts Department will present original films at this performance.

Jessica Michelle Singleton

Up-and-coming comedian Jessica Michelle Singleton brings high-energy laughs with an endearingly wild streak. She has written material and toured alongside leading comics, including Theo Von, Bert Kreischer, and Melissa Villaseñor.

Daniel Pepin live at Grove Roots

Daniel Pepin takes the stage at Grove Roots for a live performance that brings a night of music and more.

Golfing for Glory

Golfing for Glory is a charity golf tournament at Cypresswood Golf & Country Club, hosted by Veterans Outdoor Ministries to support faith-based outdoor programs for veterans. The competition follows a four-person scramble format and brings together players, sponsors, and supporters for a day centered on friendly competition, fellowship, and purpose. Early bird pricing is available for a limited time, with individual entry set at $100 and a four-person team priced at $400.

Veterans Outdoor Ministries 1st Annual Golfing Charity Event, CYPRESSWOOD GOLF & COUNTRY CLUB

This first annual charity golf event at Cypresswood Golf & Country Club supports Knights of Columbus St. Mary Council 4444 and fills the course with contests and standout prizes. The KRANK It Hole gives every golfer a chance to win a swing speed specific Formula KRANK driver valued at $700, and a long drive competition will be held with Open and Seniors or Women divisions. A featured Hero Hole offers a $1,000 hole in one prize plus closest to the pin awards for first and second. Two hit the green challenges raise the stakes, with one offering a chance at up to $50,000 and another featuring a $2,800 Cancun five day, four night stay. Both challenge holes also come with a shot at $5,000 dual stays through the "The World Is Yours" travel prize, and rare collector’s edition Hero Drivers may be available. For details, contact Justin at 570-484-1863.

The Good, The Bad, and The Twizted

Twizted returns to LA's Midway Saloon for a rock and roll show.

Winter Haven Farmers Market

The market showcases local farmers, food trucks, and makers. Offerings include fresh produce, handmade pasta, baked goods, meats, seafood, and plants, plus items crafted by local artisans.

SOLD OUT — 🔥 JERK & JAM FESTIVAL

Food lovers and market browsers can find plenty to enjoy at the Saturday Shoppes Jerk & Jam Festival, from big, flavorful bites to distinctive handcrafted goods. Located in Lakeland, this lively gathering offers a Saturday outing with tastes and makers all in one place.

Scenic Maui - Sunset

This event is open to painters ages 15 and up, and those under 18 must be accompanied by a paid adult. During the class, you can purchase wine, beer, and non-alcoholic beverages. You are welcome to bring your own snacks. If you would like to make your own scented soy candle, you may do so for an additional fee, but you must arrive 30 minutes early.

Jessica Michelle Singleton

See Jessica Michelle Singleton perform live.

WE ARE HERE TO PARTY WITH YOU !!!

A lakeside party offers drinks, great food, and time with friends. Rock and roll from the 70s, 80s, and 90s sets the vibe, and there may be surprises along the way. A love of a good challenge keeps the energy high.

Walter Parks

Gram Parsons Derry Down hosts a night with Walter Parks, a guitarist, singer, and songwriter whose original work and tributes are steeped in the sounds and stories of the Okefenokee Swamp, the headwaters of the Suwannee River near his North Florida roots. His research and imaginative reinterpretations of hollers, hymns, and reels from swamp homesteaders are preserved in the American Folklife Collection at the Library of Congress. For ten years he toured and recorded worldwide with Woodstock icon Richie Havens, performing at venues such as Carnegie Hall and Madison Square Garden, as well as the Glastonbury Festival in England. In 2014 he served as Judy Collins’s sole accompanist at her Lincoln Center tribute to Pete Seeger. Parks also leads two Americana-rooted ensembles, Swamp Cabbage (electric folk rock) and The Unlawful Assembly (reimagined spirituals). Now based in St. Louis, he co-produces The Concert at The Burroak with his wife, Margo. Admired by artists like JJ Grey, Judy Collins, and Rockwood Music Hall’s Ken Rockwood, he is celebrated for a voice and guitar style that can be both tender and thunderous. Expect an intimate evening of swamp-sourced tradition, modern grit, and soulful storytelling.

A Day in the Life

Interest Meeting

Learn about Haven Hybrid Academy at an interest meeting focused on the academy’s offerings and how the program is organized. The session provides an overview and includes time for questions so attendees can get the information they need.

A Hidden Gem

Try something new and create your own long-lasting, all-natural scented soy candle before you paint! Look for the DIY CANDLE add-on option during your event registration. Arrive a little early to get settled. If you’re coming with others, give the group’s name in the Special Request box and the venue will seat you together. You are welcome to bring your favorite bottle of wine or beer and other food or snacks. The venue provides cups and cork screws. These classes are intended for adult painters, although painters aged 15 to 20 are permitted with the understanding that you must be at least 21 to consume alcohol in the studio. Younger painters can participate in Family Classes and Kids Classes.

Samantha Fish and more

Samantha Fish delivers thrilling live entertainment, turning a night out with friends or a long-awaited plan into something special. Tickets are available as long as seats remain.

Hot Ghost Summer - BLACKLIGHT

This event is for those 18 years and up. You can share this blacklight event with friends. An instructor will guide you through the painting process. Guests can enjoy a variety of wine, beer, and non-alcoholic beverages, and are welcome to bring their own snacks. Payment is required at the time of booking to reserve your seat.

Galactic Moonlight

Enjoy step-by-step instruction with an experienced and enthusiastic artist to create your own unique painting. You can also create your own long-lasting, all-natural scented soy candle before you paint for an additional fee. The event is open to painters ages 15 and up, with painters ages 15+ able to attend with a paid adult. Participants can purchase wine, beer, and non-alcoholic beverages, and snacks are allowed.

Gnarly Quinn: Kevin's B-Day Bash @ LA's!

Gnarly Quinn travels to LA's for a birthday bash honoring drummer Kevin. This celebration keeps the focus on marking his big day with the band at the venue.

Island View - Set - DATE NIGHT- BLACK LIGHT

Interest Meeting

Learn about Haven Hybrid Academy at an interest meeting hosted at Southside Baptist Church. The session will cover the academy’s offerings and explain how the program is structured. Attendees will have time to ask questions and get the details they need.

Carry Me Back Rock N Roll!

A Twizted good time awaits as this rock and roll night returns to Out-n-About Bar and Music Lounge.

La Midway Presents X it 7 Live

Presented by La Midway, this live performance features X it 7 sharing brand new songs with the audience. The artists express enthusiasm about seeing everyone and offer a warm message of appreciation.

Winter Haven Saturday Markets

This Saturday market takes place in Winter Haven, Florida and is organized by Winter Haven Saturday Market.

Circuit of Champion FLORIDA

Presented by Premier Tournament Group and Big Time Hoops, this Florida basketball tournament brings together teams from multiple states for exciting competition.

Summer in the Gorge

Enjoy a painting session for ages 15 and up. Instruction will be provided. You can purchase wine, beer, or non-alcoholic beverages at the bar. It is also permissible to bring your own snacks. If youd like to create your own scented soy candle before the painting, arrive 30 minutes early.

Almost There Live at Caribbean Bay - Winter Haven, FL

Almost There brings a full set to Caribbean Bay in Winter Haven, spanning rock, metal, alternative, pop, and classics with a progressive edge. The show leans into bold, unfiltered delivery rather than safe choices and may include a few originals. Frozen rum runners set the scene while the band leans into a heavy vibe.

Demon Tiger - Black Light

Attend a painting event and create your own version of Demon Tiger using black lights. This activity is for ages 15 and up, those under 18 must be accompanied by a paid adult. You can purchase wine, beer, seltzer, and cider. You can also create your own scented soy candle before you start painting for an additional fee.

Arabellas Pre-Show Dinner Special

Turn Tribute Tuesday into an Italian night out with an exclusive four-course pre-show dinner in Winter Haven. Begin with an antipasto choice such as creamy burrata caprese, crispy mozzarella in carrozza, or rich fiocchi al gorgonzola, followed by a fresh Insalata della Casa. For the main course, select from honey dijon glazed salmon, NY strip tagliata di manzo, fettuccine Alfredo, Arabellas homemade lasagna, or classics like piccata, parmigiana, or marsala prepared with chicken or veal. A chef-chosen dessert completes the meal. Vegetarian options are available, and most allergies can be accommodated. No substitutions are permitted; beverages, gratuity, and alcoholic drinks are not included.

Pokemon League Challenge - May 2026

This monthly Pokémon League Challenge features Standard Format play with 25 minute, best of one games. The tournament will run for 3 to 4 rounds depending on attendance and is expected to last about two and a half hours. Entry is $5. Participation is capped at 16 players, and preregistration by phone is required at 863-324-1323. Prize support includes one prize pack for each match win, an additional pack for the top four, and a pack for every participant. Players must arrive with a completed decklist that lists first and last name, Pokémon ID number, date of birth, and the exact quantities and versions of all cards in the deck. Late arrivals or missing decklists will result in ineligibility to play.

Storm Riders - Ritz Theater Winter Haven FL

Storm Riders make their first appearance at the Ritz Theatre. Ticket sales are open, and seat selection is available.

By the Moon and the Stars

Sunset Splendor

Enjoy a painting class for ages 15 and up. An instructor will guide you step by step as you create your own artwork. You can purchase wine, beer, and non-alcoholic beverages. You can also bring your own snacks. If you want to make your own scented soy candle before you paint, please arrive early. There are upgrades available.

Magic - Final Friday Pauper

Players can enter for $10. The event uses 50-minute Swiss rounds with best-of-three matches. For prize support, one ticket is awarded for each match win, plus an extra ticket for placing in the top four. Tickets can be redeemed for a variety of booster packs. First place receives a foil promo pack, and additional promo packs will be given out at random.

Vibrant Forest

Enjoy a guided painting session suitable for ages 15 and up. An instructor will provide step-by-step directions as you create your own unique artwork. You can also create your own scented soy candle before you paint, but you will need to arrive 30 minutes early if you choose to make a candle. Wine, beer, and non-alcoholic beverages are available for purchase, and you may bring your own snacks.

Live at Raise The Bar and Grill !

Attendees can enjoy live music along with food and drinks at Raise the Bar and Grill. It offers a chance to pair live tunes with something to eat and drink in one place.

Dinner & Movie

This free monthly get-together includes dinner followed by a movie. For headcount planning, please call the church office at (863) 439-1268 with the number in your party.

Drive-In Dreams - 50' Party

Cypresswood Golf & Country Club hosts a retro celebration with DJ Dan spinning favorites, a buffet inspired by the 50s, and opportunities for door prizes. Join in contests and games, enjoy a cash bar with specialty drinks, and capture photos with classic 1950 cars. 50s attire is encouraged. Admission is $45 per person.

Smokepoint Returns to Tanners Lakeside

Smokepoint brings live music to Tanners Lakeside, creating an easygoing night out by the water. The venue offers drink selections and food, so you can relax with something to eat and sip while the band plays.

Sip Swap Swag

Bring a gently used clothing donation to Jessie’s Lounge, browse the selection, and take home items you like at no cost while enjoying drinks. This clothing swap blends sipping and sharing with a focus on giving back. All donations go to the George Jenkins Community of Hope Shelter to support families facing emergencies.

A Night of Magic and Sophisticated Buffoonery

A previously sold-out evening of magic and refined silliness comes to Winter Haven, offering an escape filled with illusions and laughter. Award-winning entertainer Cody Byrns leads the show.

Wildflowers with a Butterfly

The Great American Beer & Wine Tasting

Main Street Winter Haven hosts a tasting experience celebrating America 250, 1776 to 2026. The annual Beer & Bubbles tradition has been refreshed as The Great American Beer & Wine Tasting, presented by Bank of Central Florida Winter Haven, to honor the nation’s 250th anniversary. Participating downtown businesses will offer pairings of American beer or wine with classic American bites. Attendees can secure tasting tickets in advance, or at the door if available, then present an ID and check in at one of two stations to collect a tasting glass and a map. Tasting tables at each stop will feature an All American theme.

Gladiator / Gladiatrix Wrestling Series

Open to wrestlers ready to compete and grow, this series offers a welcoming way to showcase skills, refine technique, and build connections within the wrestling community. Regional qualifying events are set for Des Moines, Iowa, Asheville, North Carolina, and Winter Haven, Florida, providing multiple entry points into the action. Registration is open for competitors who want to make their mark.

Save The Date - Pitties & Pearls, The Masquerade Edition

The second annual Pitties & Pearls fundraiser, presented by Adams Estate, returns as The Masquerade Edition. The event will be held at Adams Estate. Further details will be announced soon.

Service clinic event

This service clinic offers complimentary multi-point inspections and a complimentary warranty coverage review. Enjoy complimentary food and refreshments while attending. There will be giveaway prizes and raffles. Reservations can be made by scanning as indicated, and RSVPs are requested.

2026 Juneteenth Celebration

Presented by the City of Winter Haven, this annual community-wide Juneteenth celebration takes place at the new Winter Haven Recreation and Cultural Center. The event honors the significance of Juneteenth and highlights culture, heritage, and accomplishments with live music and other performances, local food and shopping from area vendors, family activities, and educational exhibits. Vendor applications and additional details will be shared soon, and the gathering centers on celebration, reflection, and unity.

Grove Roots Brewing in Winter Haven

Enjoy tavern style pizza prepared in small batches.

Fan the flames of Rock n Roll with Twizted!

Twizted returns to Out-n-About Bar and Music Lounge with another surge of rock and roll. Back to turn it up again and keep the music roaring.

Sip N’ Stitch 1 Year Anniversary Celebration!

Celebrate one year of Sip N’ Stitch at Grove Roots with a stitching gathering that brings together the community built over the past year. Snacks will be available, and beer will be available for purchase at the bar.

Almost There Live at Somewhere Sports Bar - Winter Haven, FL

Almost There performs an outdoor parking lot set at Somewhere Sports Bar in Winter Haven, featuring rock, metal, alternative, pop, and classics. The set may include a few newly learned requests from friends, adding surprises to a high-energy night of live music.

Daniel Pepin live at Grove Roots

A music-filled night awaits, with more to enjoy.

Party It Up At The Bay

At Caribbean Bay, this party channels the Bay’s upbeat vibe with a TwiZted twist.

Maurice Benard in Winter Haven, FL

An evening with Maurice Benard brings inspiration, reflection, and General Hospital memories along with a question and answer session. The star of ABC’s General Hospital, a New York Times bestselling author and host of the YouTube series State of Mind, highlights more than three decades as Sonny Corinthos. Cast in 1993, he has received multiple Daytime Emmy nominations and earned wins in 2003, 2019, and 2021. On screen he portrays a mobster who grapples with manic depression, and in his own life he has been diagnosed with bipolar disorder and advocates for mental health. Tickets are available in two options. General admission is $49, and taxes and fees apply. VIP admission is $99, and taxes and fees apply, and includes a meet and greet after the show with photo opportunities. Autographs are not included.