Best events in
Winter Garden

Looking for events or things to do in Winter Garden, FL? The city's social life revolves around its charming historic downtown, where brick-paved streets and the West Orange Trail create a lively, walkable hub. From the bustling Plant Street Market to live performances at the Garden Theatre, the area offers a relaxed, community-focused scene.

Spend an afternoon exploring historic downtown, where the West Orange Trail leads to independent shops, al fresco dining, and the artisan vendors at Plant Street Market.
Catch recurring live music at the weekly Fridays on the Plaza series in Centennial Plaza or on the patio at Crooked Can Brewing Company.
See a play, concert, or film at the Garden Theatre, a restored 1935 Art Deco venue that serves as a cultural anchor on Plant Street.

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After 8pm

Weekends At The Grove| Harlow Grove

Tomorrow • 9:00 PM + 1 more

Harlow Grove

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Nightmare On Plant Street

Fri, Oct 30 • 8:00 PM + 1 more

The Whole Enchilada Fresh Mexican Grill & Bar

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Classic Weekend Edition: RnB Up-N-Smoke

Fri, Nov 20 • 9:00 PM

Mist Hookah Lounge

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Vibrance - The Back In Times Edition

Sat, Dec 12 • 9:00 PM

10892 W Colonial Dr

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Weekends At The Grove| Harlow Grove

Tomorrow • 9:00 PM + 1 more

Harlow Grove

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Nightmare On Plant Street

Fri, Oct 30 • 8:00 PM + 1 more

The Whole Enchilada Fresh Mexican Grill & Bar

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Classic Weekend Edition: RnB Up-N-Smoke

Fri, Nov 20 • 9:00 PM

Mist Hookah Lounge

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Vibrance - The Back In Times Edition

Sat, Dec 12 • 9:00 PM

10892 W Colonial Dr

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Popular in Winter Garden

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Marketing on Tap

Wed, Oct 14 • 6:30 PM

Windermere Brewing Company

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Pop - Up Balance & Glow "REDESCÚBRETE" Una nueva etapa

Sat, Oct 17 • 2:00 PM

Legend Martial Arts Sport Center

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Hot Girl Walk® | Orlando | October 18

Sun, Oct 18 • 9:30 AM

West Orange Trail - Winter Garden Station - https://maps.app.goo.gl/NUEPcJcicVYKTQie7?g_st=ac

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Divas For The Cause Breast Cancer Awareness Brunch

Sun, Oct 18 • 12:30 PM

1201 Black Lake Blvd

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Behind the Production

Wed, Oct 21 • 11:30 AM

209 Capitol Ct

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2nd Annual Pumpkin Carving Potluck

Sun, Oct 25 • 4:00 PM

Windermere Town Hall

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November OBSE

Thu, Nov 5 • 9:30 AM

146 W Plant St

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Oranges and Ornaments: A Festival of Trees and Wreaths

Fri, Nov 20 • 5:30 PM

The Winter Garden Heritage Foundation - Healthy West Orange Heritage and Cultural Center

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Marketing on Tap

Wed, Oct 14 • 6:30 PM

Windermere Brewing Company

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Pop - Up Balance & Glow "REDESCÚBRETE" Una nueva etapa

Sat, Oct 17 • 2:00 PM

Legend Martial Arts Sport Center

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Hot Girl Walk® | Orlando | October 18

Sun, Oct 18 • 9:30 AM

West Orange Trail - Winter Garden Station - https://maps.app.goo.gl/NUEPcJcicVYKTQie7?g_st=ac

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Divas For The Cause Breast Cancer Awareness Brunch

Sun, Oct 18 • 12:30 PM

1201 Black Lake Blvd

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Behind the Production

Wed, Oct 21 • 11:30 AM

209 Capitol Ct

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2nd Annual Pumpkin Carving Potluck

Sun, Oct 25 • 4:00 PM

Windermere Town Hall

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November OBSE

Thu, Nov 5 • 9:30 AM

146 W Plant St

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Oranges and Ornaments: A Festival of Trees and Wreaths

Fri, Nov 20 • 5:30 PM

The Winter Garden Heritage Foundation - Healthy West Orange Heritage and Cultural Center

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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 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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Humanitarian Water Engineering Fall 2026

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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 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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Humanitarian Water Engineering Fall 2026

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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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Elemental Energy

Tomorrow • 7:00 PM

95 E Palmetto St

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Winter Garden Railroad Mystery Quest

Tomorrow • 4:00 PM + 8 more

101 W Plant St

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Weekends At The Grove| Harlow Grove

Tomorrow • 9:00 PM + 1 more

Harlow Grove

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BECOME A TRAVEL BUSINESS OWNER | Ocoee, FL

Tomorrow • 9:00 PM

Fairfield Inn & Suites Orlando Ocoee

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Nona Nerds Presents: TEAM ROCKET TAKES OVER OCOEE!

Saturday • 12:30 PM

125 N Bluford Ave

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Weekends in Winter Garden: Foodies + New Friends

Sunday • 7:00 PM

Restaurant of the Weekend

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Rooted Walk- Wellness Walk for Women

Sunday • 8:30 AM

Chapin Station

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Game Days At AJ's Pizza Joint

Sunday • 1:00 PM

AJ's Pizza Joint

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Elemental Energy

Tomorrow • 7:00 PM

95 E Palmetto St

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Winter Garden Railroad Mystery Quest

Tomorrow • 4:00 PM + 8 more

101 W Plant St

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Weekends At The Grove| Harlow Grove

Tomorrow • 9:00 PM + 1 more

Harlow Grove

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BECOME A TRAVEL BUSINESS OWNER | Ocoee, FL

Tomorrow • 9:00 PM

Fairfield Inn & Suites Orlando Ocoee

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Nona Nerds Presents: TEAM ROCKET TAKES OVER OCOEE!

Saturday • 12:30 PM

125 N Bluford Ave

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Weekends in Winter Garden: Foodies + New Friends

Sunday • 7:00 PM

Restaurant of the Weekend

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Rooted Walk- Wellness Walk for Women

Sunday • 8:30 AM

Chapin Station

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Game Days At AJ's Pizza Joint

Sunday • 1:00 PM

AJ's Pizza Joint

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Points of Interest near Winter Garden

Winter Garden Ghost Tours And Investigations By American Ghost Adventures Rated 1

Winter Garden Fountain In The Median

Frequently asked questions about Winter Garden

Where can I find live music events in Winter Garden?

Crooked Can Brewing Company and Fridays on the Plaza are great spots for live music. The brewery hosts acoustic sets on its patio, while the weekly Fridays on the Plaza series brings free performances to the heart of downtown for a relaxed, outdoor-friendly experience.

What are some family-friendly things to do in downtown Winter Garden?

The Winter Garden Farmers Market is a popular family outing every Saturday morning. This large weekly event features over 100 vendors, food, and live entertainment at the Downtown Pavilion. Afterward, many families stroll or bike along the adjacent West Orange Trail.

Are there any free events in Winter Garden?

Yes, the weekly Fridays on the Plaza music series is a popular free event. Additionally, the Winter Garden Farmers Market offers free admission, and many people enjoy simply walking or cycling through historic downtown and along the West Orange Trail without charge.

What's a good spot for a casual date night with food and drinks?

Plant Street Market offers a lively setting for a date. You can grab a craft beer from Crooked Can Brewing Company and choose from around 20 artisan food vendors in a lively, communal atmosphere that often features live music.

How can I experience the local arts and culture scene?

The Garden Theatre is the cultural heart of historic downtown. This restored 1935 venue presents a mix of stage plays, musicals, concerts, and films. For a taste of local crafts, the Winter Garden Farmers Market features many artisan vendors.

What is there to do outdoors in Winter Garden?

The West Orange Trail is central to outdoor activity, perfect for biking and walking. Many local events also have an outdoor component, like the weekly farmers market at the Downtown Pavilion or live music on the patio at Crooked Can Brewing.

Is there a recurring weekly event for nightlife in Winter Garden?

Crooked Can Brewing Company hosts a weekly Live Team Trivia Night. It's a fun and social event that draws a regular crowd to the popular brewery inside Plant Street Market, combining craft beer with friendly competition.

Does Winter Garden have any social fitness events?

The Crooked Can Run Club meets for a weekly run on Tuesday nights. It's a community-focused fitness event that combines exercise with socializing, as participants can enjoy discounted beers at the brewery after their run.