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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CITY LIGHTS: LIGHTHOUSE

Today • 7:45 PM

West Orange Dream Center

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Taste Of Fall

Tomorrow • 10:00 AM

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October OBSE

Thursday • 9:30 AM

146 W Plant St

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K-Pop Circus Show – Ocoee, FL

Fri, Oct 2 • 5:00 PM + 1 more

Lakeshore Center

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Photography Class

Mon, Oct 5 • 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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Orlando Adult Golf Night Pt.3

Fri, Oct 16 • 6:30 PM

Stoneybrook West Golf Club

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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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CITY LIGHTS: LIGHTHOUSE

Today • 7:45 PM

West Orange Dream Center

Check ticket price on event

Taste Of Fall

Tomorrow • 10:00 AM

Select Locations

Check ticket price on event

October OBSE

Thursday • 9:30 AM

146 W Plant St

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K-Pop Circus Show – Ocoee, FL

Fri, Oct 2 • 5:00 PM + 1 more

Lakeshore Center

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Photography Class

Mon, Oct 5 • 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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Orlando Adult Golf Night Pt.3

Fri, Oct 16 • 6:30 PM

Stoneybrook West Golf Club

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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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Marketing Breakthrough: 40X Your Holistic Business [$297 Value]

Sunday • 10:00 AM PDT

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Online Group Reading - September 27

Sunday • 8:00 PM ADT

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Barnes & Noble and Waterstones Virtually Presents: Madeline Miller

Tuesday • 2:00 PM EDT

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Black Girl Book Fair! Spooky Edition

Sat, Oct 3 • 12:00 AM CDT

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Ethically Shady: Navigating the Gray Areas of Interpreting

Sat, Oct 3 • 10:00 AM PDT

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A Norman stitch-up? The story behind the Bayeux Tapestry

Wed, Oct 7 • 7:30 PM GMT+1

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(ONLINE) Women on the Move with Ann Patchett

Tue, Oct 27 • 11:30 AM EDT

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Washington Crossing the Delaware / The Crossing - Film History Livestream

Sat, Dec 19 • 8:00 PM EST

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Marketing Breakthrough: 40X Your Holistic Business [$297 Value]

Sunday • 10:00 AM PDT

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Online Group Reading - September 27

Sunday • 8:00 PM ADT

Check ticket price on event

Barnes & Noble and Waterstones Virtually Presents: Madeline Miller

Tuesday • 2:00 PM EDT

Check ticket price on event

Black Girl Book Fair! Spooky Edition

Sat, Oct 3 • 12:00 AM CDT

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Ethically Shady: Navigating the Gray Areas of Interpreting

Sat, Oct 3 • 10:00 AM PDT

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A Norman stitch-up? The story behind the Bayeux Tapestry

Wed, Oct 7 • 7:30 PM GMT+1

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(ONLINE) Women on the Move with Ann Patchett

Tue, Oct 27 • 11:30 AM EDT

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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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CITY LIGHTS: LIGHTHOUSE

Today • 7:45 PM

West Orange Dream Center

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Winter Garden Railroad Mystery Quest

Today • 4:00 PM + 8 more

101 W Plant St

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Weekends At The Grove| Harlow Grove

Today • 9:00 PM + 1 more

Harlow Grove

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Carry His Word in style

Tomorrow • 1:00 PM

West Orange Dream Center

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Taste Of Fall

Tomorrow • 10:00 AM

Select Locations

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Full Moon Crystal Intention Workshop

Tomorrow • 7:00 PM

95 E Palmetto St

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Weekends in Winter Garden: Foodies + New Friends

Sunday • 7:00 PM

Restaurant of the Weekend

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Game Days At AJ's Pizza Joint

Sunday • 1:00 PM

AJ's Pizza Joint

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CITY LIGHTS: LIGHTHOUSE

Today • 7:45 PM

West Orange Dream Center

Check ticket price on event

Winter Garden Railroad Mystery Quest

Today • 4:00 PM + 8 more

101 W Plant St

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Weekends At The Grove| Harlow Grove

Today • 9:00 PM + 1 more

Harlow Grove

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Carry His Word in style

Tomorrow • 1:00 PM

West Orange Dream Center

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Taste Of Fall

Tomorrow • 10:00 AM

Select Locations

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Full Moon Crystal Intention Workshop

Tomorrow • 7:00 PM

95 E Palmetto St

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Weekends in Winter Garden: Foodies + New Friends

Sunday • 7:00 PM

Restaurant of the Weekend

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Game Days At AJ's Pizza Joint

Sunday • 1:00 PM

AJ's Pizza Joint

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Food & Drink events

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Up To No Good Thursdays | Harlow Grove

Thu, Oct 1 • 8:00 PM + 51 more

Harlow Grove

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UNO Winter Garden - Deep Dish Pizza Cooking Class and Lunch

Sat, Oct 3 • 12:00 PM + 3 more

UNO Pizzeria & Grill

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ABC Winter Garden Premium Wine Tasting Experience

Wed, Nov 11 • 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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Up To No Good Thursdays | Harlow Grove

Thu, Oct 1 • 8:00 PM + 51 more

Harlow Grove

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UNO Winter Garden - Deep Dish Pizza Cooking Class and Lunch

Sat, Oct 3 • 12:00 PM + 3 more

UNO Pizzeria & Grill

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ABC Winter Garden Premium Wine Tasting Experience

Wed, Nov 11 • 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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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.