winterhavenfoodtours

Antoine P brings some of Central Florida’s rising comedy talent to Laugh Out Lounge for a fast-paced night of live stand-up. 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. Present your confirmation email or QR Read more...

Come with friends and enjoy three wine samples paired with pizza and a side salad at The Treasured Olive. Tickets are listed at $49.87 through the organizer’s Eventbrite page. Official details and tickets: https://www.eventbrite.com/e/pizza-wine-night-winter-haven-tickets-1993492605045 Read more...

Live & Loud is Polk County’s monthly showcase of rising bands and local creative talent. The September lineup features 69 Fingers from Orlando, Ciquet from Lakeland, Lot Lizards from Tampa, and an additional act to be announced. Produced with Punk Kid Productions LLC. Official details and tickets: https://theatrewinterhaven.com/event/live-loud-at-the-ritz-8/ Read more...

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...

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...

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...

Main Street Winter Haven’s 10th Annual Wine, Chocolate & Cheese event invites guests to sample curated wine-and-chocolate or wine-and-cheese pairings at more than 40 Downtown Winter Haven businesses. This map-based tasting event encourages attendees to explore and shop local downtown businesses. Official event details: https://www.mainstreetwh.com/event/wcc2026/ Read more...

Main Street Winter Haven’s 19th Annual Oktoberfest brings more than 30 German, American, and craft beers to Central Park in Downtown Winter Haven. Join the community for an evening celebrating Oktoberfest downtown. Official event details: https://www.mainstreetwh.com/events/list/ Read more...

Main Street Winter Haven’s Cocktail Classic is a week-long tasting experience showcasing Downtown Winter Haven’s cocktail and dining offerings. Participating venues will feature specialty cocktails and mocktails, creative appetizers, and mixology experiences. Guests can sample the offerings and vote for Best Cocktail Bar and Best Cocktail. Official details: https://www.mainstreetwh.com/tag/downtown-winter-haven/ Read more...

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...