All Events

{"hide_search_input":"","hide_near_input":"","show":"","filters_pos":"","input_size":"","bar_flex_wrap":"","bar_flex_wrap_md":"","bar_flex_wrap_lg":"","input_border":"","input_border_opacity":"","input_rounded_size":"","btn_bg":"","btn_rounded_size":"","btn_rounded_size_md":"","btn_rounded_size_lg":"","bg":"","mt":"","mr":"","mb":3,"ml":"","pt":"","pr":"","pb":"","pl":"","border":"","rounded":"","rounded_size":"","rounded_size_md":"","rounded_size_lg":"","shadow":"","css_class":""}
jessies jam 768x513

The Jam with No Name at Jessie’s Lounge - August 26, 2026

New
No Reviews
August 26, 2026, 7:00 pm
-
11:59 pm
Every Wednesday at 7 PM, The Jam with No Name—hosted by Frankie—welcomes musicians of all skill levels to perform at Jessie’s Lounge in Downtown Winter Haven. Bring an instrument, share your talent, or come enjoy live music and drinks. Official event details: https://jessieslive.com/events Read more...
Winter Haven Afternoon Flavors Walking Tour Facebook Cover 768x284

Flavors of Winter Haven Food Tour - August 27, 2026

New
No Reviews
August 27, 2026, 2:00 pm
-
5:00 pm
Price: $124
Discover the flavors, history, and locally owned restaurants of downtown Winter Haven on this guided culinary walking tour. Schedule: Tuesdays, Thursdays, and Saturdays, 2:00–5:00 p.m. All featured tastings are included. Exact meeting and parking instructions are provided with your booking. View full tour details and book now. Read more...
chef s table Facebook Cover 768x284

Winter Haven Chef’s Table Experience - August 27, 2026

New
No Reviews
August 27, 2026, 5:00 pm
-
8:00 pm
Price: $250
Enjoy an elevated guided dining experience showcasing Winter Haven chefs, restaurants, and thoughtfully prepared courses. Schedule: Thursdays and Saturdays, 5:00–8:00 p.m. Exact meeting and parking instructions are provided with your booking. Minimum guest requirements may apply. View full tour details and book now. Read more...
happy hour trivia show at barrel 239 768x1017

Happy Hour Trivia Show - August 27, 2026

New
No Reviews
August 27, 2026, 6:00 pm
-
11:00 pm
WEDNESDAYs: 🐪🥃 ▫️Trivia 6pm! ▫️Enjoy a BOGO 8pm-12am! (Like & show post to bartender) ▫️$6 VG Caramel Vodka Espresso Martinis (Mon-Thur / 6pm-9pm) ALL DAY ER-DAY DEALS: 💲 ▫️$2 Twin P Whiskey ▫️$3 Bushmills Irish Whiskey HAPPY HOUR: 🍸🍷🥂🥃 ▫️$3 off Wells & Wines ▫️$2 off Beers – Sunday & Monday! (ALL DAY) – Tuesday-Thursday! (12pm-6pm) – Friday & Saturday! Read more...
grove roots logo

Grove Roots Run Club - August 27, 2026

New
No Reviews
August 27, 2026, 6:30 pm
-
8:00 pm
Run Club departs from Grove Roots Brewing Co. at 6:30 PM. All levels are welcome, with 1.5-mile and 3-mile route options. Enjoy a friendly downtown run followed by refreshments at the brewery. Official event details: https://groveroots.com/events/category/special-event/list/ Read more...
WH Food Tours Logo

Smile City Comedy Show! with Rob Smiles

New
No Reviews
August 27, 2026, 8:00 pm
-
10:00 pm
Price: $15
Hosted and produced by Rob Smiles, Smile City Comedy Show spotlights fast-rising Central Florida comedians bringing fresh material and high-energy live stand-up to Laugh Out Lounge. Doors open at 7 PM and the show starts at 8 PM. Ages 21 and older. Two-item minimum per person. Advance tickets are $15; tickets may be $20 at the door, plus tax. Use Read more...
peace train karaoke 768x354

Peace Train Karaoke at Jessie’s Lounge - August 27, 2026

New
No Reviews
August 27, 2026, 9:00 pm
-
11:59 pm
Join Peace Train Karaoke every Thursday at 9 PM at Jessie’s Lounge in Downtown Winter Haven. Sing your favorite songs, enjoy the music, and explore the bar’s drink selection. Official event details: https://jessieslive.com/events Read more...
dj trinidad 768x768

DJ Trinidad - August 27, 2026

New
No Reviews
August 27, 2026, 9:00 pm
-
2:00 am
DJ Trinidad typically spins music out back on the patio Read more...
Coffee and Tea Tour 768x402

Winter Haven Coffee, Tea, and Dessert Tour - August 28, 2026

New
No Reviews
August 28, 2026, 10:00 am
-
3:00 pm
Price: $125
Join us on a sweet and savory journey through Winter Haven’s local coffee shops and dessert destinations. Enjoy coffee, tea, pastries, desserts, local stories, and a guided walking experience. Schedule: Mondays, Wednesdays, and Fridays, 10:00 a.m.–3:00 p.m. All tastings are included. Exact meeting and parking instructions are provided with your booking. View full tour details and book now. Read more...
Winter Haven Happy Hour Walking Tour

Winter Haven Happy Hour Pub Crawl - August 28, 2026

New
No Reviews
August 28, 2026, 4:30 pm
-
7:30 pm
Price: $157
Experience Winter Haven’s local nightlife on a guided happy-hour pub crawl featuring drinks, food, and entertaining local stories. Schedule: Wednesdays and Fridays, 4:30–7:30 p.m. Exact meeting and parking instructions are provided with your booking. Guests must meet the tour’s age requirements. View full tour details and book now. Read more...