Best events in
Windermere

With a rhythm centered on its historic downtown and serene lakes, the calendar of events and things to do in Windermere, FL reflects a close-knit community spirit. Many gatherings take place in Town Square Park, from the weekly farmers market to annual art shows and food truck nights. For a wider array of performing arts and nightlife, residents often head to neighboring Winter Garden or the Dr. Phillips area.

The social week in downtown Windermere often revolves around Town Square Park, which hosts the weekly Windermere Farmers Market and monthly Food Truck Nights.
Nearby historic Winter Garden provides another hub of activity, with classic films and live performances at the Garden Theatre.
Major Broadway tours, concerts, and comedy acts are a short drive away at the Dr. Phillips Center for the Performing Arts in Orlando.

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LEMON DROP & SEAFOOD FESTIVAL

Sun, Oct 18 • 4:00 PM

Wall Street Plaza

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Romantasy BookCon- Orlando 2026

Thu, Oct 22 • 4:00 PM

Hilton Orlando Lake Buena Vista - Disney Springs Area

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R&Boo: Orlando’s First Ever Halloween R&B Block Party

Sun, Oct 25 • 4:00 PM

Walter's Tavern

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GOOD MORNING, HERE’S BREAKFAST: CEREAL KILLER (Halloween Edition)

Sat, Oct 31 • 10:00 AM

Wall Street Plaza

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Shoot Your Shot Saturdays: Classic Weekend Edition

Sat, Nov 21 • 10:00 PM

Cosmo Downtown

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Jesus 26

Thu, Dec 3 • 7:00 PM

Addition Financial Arena

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Tiki-a-Go-Go 2027

Fri, Apr 2 • 8:00 AM

Caribe Royale Orlando

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FanGrrrl Romance Recs Premier Book Signing 2027

Thu, Sep 2 • 6:00 PM

Hilton Orlando

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LEMON DROP & SEAFOOD FESTIVAL

Sun, Oct 18 • 4:00 PM

Wall Street Plaza

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Romantasy BookCon- Orlando 2026

Thu, Oct 22 • 4:00 PM

Hilton Orlando Lake Buena Vista - Disney Springs Area

Check ticket price on event

R&Boo: Orlando’s First Ever Halloween R&B Block Party

Sun, Oct 25 • 4:00 PM

Walter's Tavern

Check ticket price on event

GOOD MORNING, HERE’S BREAKFAST: CEREAL KILLER (Halloween Edition)

Sat, Oct 31 • 10:00 AM

Wall Street Plaza

Check ticket price on event

Shoot Your Shot Saturdays: Classic Weekend Edition

Sat, Nov 21 • 10:00 PM

Cosmo Downtown

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Jesus 26

Thu, Dec 3 • 7:00 PM

Addition Financial Arena

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Tiki-a-Go-Go 2027

Fri, Apr 2 • 8:00 AM

Caribe Royale Orlando

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FanGrrrl Romance Recs Premier Book Signing 2027

Thu, Sep 2 • 6:00 PM

Hilton Orlando

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Nearby cities

Orlando

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Maitland

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Winter Park

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Sanford

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Kissimmee

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Winter Garden

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Winter Haven

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University

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Four Corners

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Alafaya

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Deltona

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Clermont

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St. Cloud

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DeLand

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Pine Hills

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Longwood

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Cocoa West

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Ocoee

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Apopka

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Leesburg

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Titusville

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Coleman

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Fairview Shores

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The Villages

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Mount Dora

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

Today • 7:30 PM GMT+1

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AI Animation Studio: Create Kids' Cartoons

Tomorrow • 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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Washington Crossing the Delaware / The Crossing - Film History Livestream

Sat, Dec 19 • 8:00 PM EST

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

Today • 7:30 PM GMT+1

Check ticket price on event

AI Animation Studio: Create Kids' Cartoons

Tomorrow • 6:00 PM EDT

Check ticket price on event

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

Check ticket price on event

Coming Together for Multilingual Children with DLD

Thu, Oct 22 • 6:00 PM GMT+2

Check ticket price on event

(ONLINE) Women on the Move with Ann Patchett

Tue, Oct 27 • 11:30 AM EDT

Check ticket price on event

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

Thu, Nov 5 • 1:00 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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Frequently asked questions about Windermere

What are some family-friendly events in Windermere?

Town Square Park hosts most of Windermere's family-friendly events. The weekly Windermere Farmers Market is a relaxed morning outing, while the monthly Food Truck Night offers live music and a variety of casual dining from September through May.

Where can I see a comedy show near Windermere?

The SAK Comedy Lab offers award-winning improv shows in nearby Winter Garden and Orlando. For a more traditional stand-up experience, the Orlando Comedy Club near International Drive features local and touring comics in a classic showroom setting.

Are there any notable annual art events in the area?

The Windermere Fine Art Show is a popular annual event that transforms downtown into an outdoor gallery. This weekend-long festival features numerous artists, live music, and food vendors, creating a lively atmosphere in the center of town.

What kind of food and drink events happen in Windermere?

Windermere hosts several signature food and drink events throughout the year. The annual Windermere Wine & Dine brings together local restaurants, while the monthly Food Truck Night offers a casual, festive atmosphere in Town Square Park.

Does Windermere have many nightlife events?

Windermere's own nightlife is generally quiet, focusing on community gatherings rather than late-night venues. For more extensive evening entertainment, including a high concentration of restaurants, locals often visit "Restaurant Row" in the nearby Dr. Phillips area.

How can I find live music events near Windermere?

Live music is a common feature at community events in Town Square Park, like the monthly Food Truck Night. For larger concerts and touring acts, residents typically go to the Dr. Phillips Center for the Performing Arts in Orlando.

What's a good date night idea that starts near Windermere?

A memorable date night could involve seeing a play or classic film at the historic Garden Theatre in Winter Garden. Afterwards, you can explore the many shops and restaurants along Plant Street for dinner or drinks.

Which free events are central to the Windermere community?

The Windermere Farmers Market is a central, free weekly event in Town Square Park. For a larger-scale experience, the Winter Garden Farmers Market is a popular free event that takes place every Saturday morning with live entertainment.

Events near Windermere

LEMON DROP & SEAFOOD FESTIVAL

Romantasy BookCon- Orlando 2026

R&Boo: Orlando’s First Ever Halloween R&B Block Party

GOOD MORNING, HERE’S BREAKFAST: CEREAL KILLER (Halloween Edition)

Shoot Your Shot Saturdays: Classic Weekend Edition

Jesus 26

Tiki-a-Go-Go 2027

FanGrrrl Romance Recs Premier Book Signing 2027

LEMON DROP & SEAFOOD FESTIVAL

Romantasy BookCon- Orlando 2026

R&Boo: Orlando’s First Ever Halloween R&B Block Party

GOOD MORNING, HERE’S BREAKFAST: CEREAL KILLER (Halloween Edition)

Shoot Your Shot Saturdays: Classic Weekend Edition

Jesus 26

Tiki-a-Go-Go 2027

FanGrrrl Romance Recs Premier Book Signing 2027

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Nearby cities

Orlando

Lakeland

Winter Park

Sanford

Kissimmee

Altamonte Springs

Maitland

Winter Garden

Winter Haven

University

Four Corners

Alafaya

Deltona

Clermont

St. Cloud

DeLand

Pine Hills

Longwood

Cocoa West

Ocoee

Apopka

Leesburg

Titusville

Coleman

Fairview Shores

The Villages

Oviedo

Mount Dora

Orange City

Casselberry

Orlando

Lakeland

Winter Park

Sanford

Kissimmee

Altamonte Springs

Maitland

Winter Garden

Winter Haven

University

Four Corners

Alafaya

Deltona

Clermont

St. Cloud

DeLand

Pine Hills

Longwood

Cocoa West