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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Popular in Winter Garden

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K-Pop Circus Show – Ocoee, FL

Tomorrow • 5:00 PM + 1 more

Lakeshore Center

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Photography Class

Monday • 5:00 PM

Newton Park

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Pumpkin Painting | The Whole Enchilada Winter Garden

Wed, Oct 14 • 7:00 PM

The Whole Enchilada Fresh Mexican Grill & Bar

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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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Oktoberfest Wiener Races

Sun, Oct 25 • 3:00 PM

Crooked Can Brewing Company

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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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December OBSE

Thu, Dec 3 • 9:30 AM

146 W Plant St

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K-Pop Circus Show – Ocoee, FL

Tomorrow • 5:00 PM + 1 more

Lakeshore Center

Check ticket price on event

Photography Class

Monday • 5:00 PM

Newton Park

Check ticket price on event

Pumpkin Painting | The Whole Enchilada Winter Garden

Wed, Oct 14 • 7:00 PM

The Whole Enchilada Fresh Mexican Grill & Bar

Check ticket price on event

Marketing on Tap

Wed, Oct 14 • 6:30 PM

Windermere Brewing Company

Check ticket price on event

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

Sat, Oct 17 • 2:00 PM

Legend Martial Arts Sport Center

Check ticket price on event

Oktoberfest Wiener Races

Sun, Oct 25 • 3:00 PM

Crooked Can Brewing Company

Check ticket price on event

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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December OBSE

Thu, Dec 3 • 9:30 AM

146 W Plant St

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Online Events

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Black Girl Book Fair! Spooky Edition

Saturday • 12:00 AM CDT

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Ethically Shady: Navigating the Gray Areas of Interpreting

Saturday • 10:00 AM PDT

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HBR Book Webinar: Resilient Optimism

Thu, Oct 15 • 1:00 PM GMT+1

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HBR Press Webinar: Resilient Optimism

Thu, Oct 15 • 8:00 AM EDT

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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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Black Girl Book Fair! Spooky Edition

Saturday • 12:00 AM CDT

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Ethically Shady: Navigating the Gray Areas of Interpreting

Saturday • 10:00 AM PDT

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HBR Book Webinar: Resilient Optimism

Thu, Oct 15 • 1:00 PM GMT+1

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HBR Press Webinar: Resilient Optimism

Thu, Oct 15 • 8:00 AM EDT

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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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Food & Drink events

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Game Days At AJ's Pizza Joint

Today • 7:00 PM + 39 more

AJ's Pizza Joint

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Game Nights at Toll Road Brewing Company - Ocoee

Today • 7:00 PM + 2 more

Toll Road Brewing Company

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Weekends At The Grove| Harlow Grove

Tomorrow • 9:00 PM + 103 more

Harlow Grove

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Now Serving Beer & Wine | Harrell's Hot Dogs + Cold Cones

Tomorrow • 11:00 AM + 90 more

Harrell's Hot Dogs + Cold Cones

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UNO Winter Garden - Deep Dish Pizza Cooking Class and Lunch

Saturday • 12:00 PM + 3 more

UNO Pizzeria & Grill

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Weekends in Winter Garden: Foodies + New Friends

Sunday • 7:00 PM + 12 more

Restaurant of the Weekend

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Exclusive French Wine Tasting Experience at ABC Winter Garden

Fri, Oct 16 • 5:30 PM

ABC Fine Wine & Spirits

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Brunch Among the Trees: An Oranges & Ornaments Culinary Experience

Sat, Nov 21 • 11:00 AM

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

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Game Days At AJ's Pizza Joint

Today • 7:00 PM + 39 more

AJ's Pizza Joint

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Game Nights at Toll Road Brewing Company - Ocoee

Today • 7:00 PM + 2 more

Toll Road Brewing Company

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Weekends At The Grove| Harlow Grove

Tomorrow • 9:00 PM + 103 more

Harlow Grove

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Now Serving Beer & Wine | Harrell's Hot Dogs + Cold Cones

Tomorrow • 11:00 AM + 90 more

Harrell's Hot Dogs + Cold Cones

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UNO Winter Garden - Deep Dish Pizza Cooking Class and Lunch

Saturday • 12:00 PM + 3 more

UNO Pizzeria & Grill

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Weekends in Winter Garden: Foodies + New Friends

Sunday • 7:00 PM + 12 more

Restaurant of the Weekend

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Exclusive French Wine Tasting Experience at ABC Winter Garden

Fri, Oct 16 • 5:30 PM

ABC Fine Wine & Spirits

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Brunch Among the Trees: An Oranges & Ornaments Culinary Experience

Sat, Nov 21 • 11:00 AM

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

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Health & Wellness events

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Rooted Walk- Wellness Walk for Women

Sun, Oct 11 • 8:30 AM

Chapin Station

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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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Yoga & Beer

Sun, Oct 18 • 10:00 AM

Crooked Can Brewing Company

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First Aid Aromatherapy

Thu, Nov 12 • 7:00 PM

95 E Palmetto St

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Rooted Walk- Wellness Walk for Women

Sun, Oct 11 • 8:30 AM

Chapin Station

Check ticket price on event

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

Sat, Oct 17 • 2:00 PM

Legend Martial Arts Sport Center

Check ticket price on event

Yoga & Beer

Sun, Oct 18 • 10:00 AM

Crooked Can Brewing Company

Check ticket price on event

First Aid Aromatherapy

Thu, Nov 12 • 7:00 PM

95 E Palmetto St

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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.