Best events in
Winter Haven

Looking for events or things to do in Winter Haven, FL? The walkable downtown core serves as a central hub where historic theaters, craft breweries, and local markets shape the local cultural rhythm. Scenic waterfront dining along the Chain of Lakes area complements an active calendar of community gatherings and live performances.

Wandering through historic Downtown Winter Haven reveals an easygoing scene featuring craft beer at Grove Roots Brewing Co. and open mic nights at Union Taproom.
Cultural arts thrive at historic venues like Theatre Winter Haven for youth series and community productions, alongside Gram Parsons Derry Down for intimate acoustic performances.
Community gatherings anchor the local schedule with the monthly Monthly block party, the weekly Winter Haven Farmers Market, and the monthly Cypress Gardens Water Ski Show on Lake Silver.

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Popular in Winter Haven

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Stormy Daniels: Unicorns in the Kitchen Tour!

Friday • 8:00 PM + 1 more

19 3rd St NW

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Ornamental Grasses

Monday • 10:00 AM

Winter Haven Public Library

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3rd Annual Homeschool Choice Expo

Sat, Oct 17 • 11:00 AM

Central Park-Downtown Winter Haven

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Winter Haven High School Athletic Hall of Fame

Sat, Oct 17 • 6:00 PM

Heartland Church

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The Gospel of the Kingdom

Fri, Oct 23 • 6:00 PM

Southside Baptist Church

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Women Veterans Expo

Sat, Oct 24 • 10:00 AM

American Legion Post 8

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Bright Futures Scholarship Information Event-Winter Haven

Tue, Oct 27 • 5:30 PM

Winter Haven Learning Resources Building-WLR 104

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Jeffrey Nothing Founder/Former Singer of MUSHROOMHEAD

Wed, Dec 9 • 5:00 PM

Jessie's

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Stormy Daniels: Unicorns in the Kitchen Tour!

Friday • 8:00 PM + 1 more

19 3rd St NW

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Ornamental Grasses

Monday • 10:00 AM

Winter Haven Public Library

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3rd Annual Homeschool Choice Expo

Sat, Oct 17 • 11:00 AM

Central Park-Downtown Winter Haven

Check ticket price on event

Winter Haven High School Athletic Hall of Fame

Sat, Oct 17 • 6:00 PM

Heartland Church

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The Gospel of the Kingdom

Fri, Oct 23 • 6:00 PM

Southside Baptist Church

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Women Veterans Expo

Sat, Oct 24 • 10:00 AM

American Legion Post 8

Check ticket price on event

Bright Futures Scholarship Information Event-Winter Haven

Tue, Oct 27 • 5:30 PM

Winter Haven Learning Resources Building-WLR 104

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Jeffrey Nothing Founder/Former Singer of MUSHROOMHEAD

Wed, Dec 9 • 5:00 PM

Jessie's

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Online Events

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AI Animation Studio: Create Kids' Cartoons

Today • 6:00 PM EDT

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HBR Press Webinar: Resilient Optimism

Thu, Oct 15 • 8:00 AM EDT

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HBR Book Webinar: Resilient Optimism

Thu, Oct 15 • 1:00 PM GMT+1

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Coming Together for Multilingual Children with DLD

Thu, Oct 22 • 6:00 PM GMT+2

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(ONLINE) Women on the Move with Ann Patchett

Tue, Oct 27 • 11:30 AM EDT

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No Title, No Permission, No Problem: Harnessing the Power of Influence

Thu, Nov 5 • 1:00 PM GMT

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The MI5 Archive: Official Secrets

Fri, Nov 27 • 2:00 PM GMT

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Washington Crossing the Delaware / The Crossing - Film History Livestream

Sat, Dec 19 • 8:00 PM EST

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AI Animation Studio: Create Kids' Cartoons

Today • 6:00 PM EDT

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HBR Press Webinar: Resilient Optimism

Thu, Oct 15 • 8:00 AM EDT

Check ticket price on event

HBR Book Webinar: Resilient Optimism

Thu, Oct 15 • 1:00 PM GMT+1

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Coming Together for Multilingual Children with DLD

Thu, Oct 22 • 6:00 PM GMT+2

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(ONLINE) Women on the Move with Ann Patchett

Tue, Oct 27 • 11:30 AM EDT

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No Title, No Permission, No Problem: Harnessing the Power of Influence

Thu, Nov 5 • 1:00 PM GMT

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The MI5 Archive: Official Secrets

Fri, Nov 27 • 2:00 PM GMT

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Washington Crossing the Delaware / The Crossing - Film History Livestream

Sat, Dec 19 • 8:00 PM EST

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This Weekend

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FLORIDA PRO WRESTLING - at Tanners Lakeside

Friday • 8:00 PM

Tanners Lakeside Restaurant & Bar

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Stormy Daniels: Unicorns in the Kitchen Tour!

Friday • 8:00 PM + 1 more

19 3rd St NW

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Spooky Hunt: Winter Haven Love, Lakes & Legends Quest

Friday • 4:00 PM + 8 more

Central Park

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Gather for Good: Winter Haven | Dinner Benefit for Wheels of Success

Saturday • 7:00 PM

Gigi KDC Cuisine & Bakery

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FLORIDA PRO WRESTLING - at Tanners Lakeside

Friday • 8:00 PM

Tanners Lakeside Restaurant & Bar

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Stormy Daniels: Unicorns in the Kitchen Tour!

Friday • 8:00 PM + 1 more

19 3rd St NW

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Spooky Hunt: Winter Haven Love, Lakes & Legends Quest

Friday • 4:00 PM + 8 more

Central Park

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Gather for Good: Winter Haven | Dinner Benefit for Wheels of Success

Saturday • 7:00 PM

Gigi KDC Cuisine & Bakery

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Music events

SUNDAZE AT KULTURE ON 1ST

Sunday • 8:00 PM + 22 more

KULTURE ON 1ST

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TRAP VS R&B w/Mix REGGAE (SIP & PAINT)

Fri, Oct 30 • 9:00 PM

KULTURE on 1st

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Chili cookoff and Trunk or Treat

Fri, Oct 30 • 6:00 PM

The Church of Jesus Christ of Latter-day Saints

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Earshot & The Lonely Ones make it to Jessie’s on their Florida tour

Fri, Nov 13 • 5:00 PM

Jessie's

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SUNDAZE AT KULTURE ON 1ST

Sunday • 8:00 PM + 22 more

KULTURE ON 1ST

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TRAP VS R&B w/Mix REGGAE (SIP & PAINT)

Fri, Oct 30 • 9:00 PM

KULTURE on 1st

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Chili cookoff and Trunk or Treat

Fri, Oct 30 • 6:00 PM

The Church of Jesus Christ of Latter-day Saints

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Earshot & The Lonely Ones make it to Jessie’s on their Florida tour

Fri, Nov 13 • 5:00 PM

Jessie's

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Points of Interest near Winter Haven

Waldo Wrights Flying Service

Frequently asked questions about Winter Haven

Where can people find live music events in Downtown Winter Haven?

Downtown Winter Haven offers lively venues like Gram Parsons Derry Down for listening sessions and Union Taproom for casual music events. Attendees enjoy sets ranging from open mic nights to acoustic concerts in historic settings. Local pub spaces also combine crafts and live stage performances for an easygoing social rhythm.

What are top family-friendly events around Lake Silver?

Lake Silver hosts the monthly Cypress Gardens Water Ski Show, drawing families to the waterfront for free aquatic events. Downtown scavenger hunts like Main Street Monsters provide seasonal activities across walkable streets. Families also head to Incredibowl Entertainment for arcade games and bowling to extend evening outings.

Which venues offer comedy shows and classic films in town?

The Historic Ritz Theatre stands out for comedy shows and classic film screenings inside a restored 1920s downtown movie house. Theatre Winter Haven also stages community theatre, youth series, and special entertainment productions. Both locations showcase local performing arts within historic architectural landmarks.

Are there free events available in Winter Haven, FL?

Free events feature prominently downtown, highlighted by the monthly Monthly block party with live music and local car displays. Central Park hosts community gatherings, while Lake Silver features monthly water ski performances. Visitors can also explore the weekly Winter Haven Farmers Market without an admission fee.

How does the food and drink scene shape local nightlife?

Downtown craft spots like Grove Roots Brewing Co. pair local beers with food trucks and casual social gatherings. Annual gatherings such as Wine, Chocolate, and Cheese bring tasting pairings to local storefronts. Nightlife flows naturally from lakeside dinners near the Chain of Lakes to downtown cocktail lounges.

Can visitors plan romantic date night ideas in the city?

A great date night begins with dinner along the Chain of Lakes followed by live performances downtown. Couples can attend a show at Theatre Winter Haven or enjoy quiet drinks at a local cocktail lounge like Barrel 239. Walkable brick streets provide a charming backdrop for evening strolls.

Which historic districts showcase art events and local markets?

Downtown Winter Haven serves as the historic district for art events, featuring the weekly Winter Haven Farmers Market. Crafts, produce, and artisan vendors fill the brick avenues during market gatherings. Annual craft beer festivals like Oktoberfest in Central Park add seasonal energy to the historic urban core.

Does outdoor recreation feature in local community programming?

Waterfront parks and interconnected lakes host outdoor activities throughout the year, including monthly ski shows on Lake Silver. Quiet residential neighborhoods like Orangewood offer tree-lined avenues for evening walks near downtown parks. Central Park acts as a hub for open-air festivals and community gatherings.