Best events in
Winter Park

Looking for events or things to do in Winter Park, FL? The city's cultural life revolves around Park Avenue's gallery scene and the professional productions at local theatres. Its character is defined by a more relaxed pace than Orlando, with an emphasis on outdoor art festivals and community gatherings in its many parks.

The walkable stretch of Park Avenue serves as a central hub, with boutiques and sidewalk cafes leading to museums and performance spaces like the Annie Russell Theatre.
The Winter Park Farmers' Market is a beloved weekly morning institution, transforming the old train depot into a lively social center.
Venues like The Winter Park Playhouse and Blue Bamboo Center for the Arts offer a range of professional musical theatre and eclectic live performances.

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Tropical Thursday : Aroma X Athenea

Thursday • 9:00 PM

Aroma Gastro Bar

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Aroma After Dark

Sat, Oct 17 • 10:00 PM + 23 more

Aroma Gastro Bar

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ACOTAR 6 Midnight Release Party!

Mon, Oct 26 • 10:00 PM

Writer's Block Bookstore

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Blues Guitarist Albert Cummings

Fri, May 14 • 8:00 PM

Blue Bamboo Center for the Arts

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Tropical Thursday : Aroma X Athenea

Thursday • 9:00 PM

Aroma Gastro Bar

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Aroma After Dark

Sat, Oct 17 • 10:00 PM + 23 more

Aroma Gastro Bar

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ACOTAR 6 Midnight Release Party!

Mon, Oct 26 • 10:00 PM

Writer's Block Bookstore

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Blues Guitarist Albert Cummings

Fri, May 14 • 8:00 PM

Blue Bamboo Center for the Arts

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Popular in Winter Park

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4th Annual Florida Food is Medicine Symposium

Thursday • 8:00 AM

Center for Health and Wellbeing

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This Is How We Brunch | Brunch, Beats & Better Sundays

Sunday • 12:00 PM

Aroma Gastro Bar

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Environmental Advocacy Symposium

Fri, Oct 16 • 9:00 AM + 1 more

Barry University School of Law - Moot Courtroom

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Swing Swing with Steve Roman and his orchestra a tribute to Sammy Davis Jr

Fri, Oct 16 • 7:00 PM

Aloma Cinema & Grill

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Fall Jazz & Blues Concert

Sat, Oct 17 • 7:00 PM

Harry P Leu Gardens

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Free Movie for Seniors: Lucy Shimmers and the Prince of Peace

Mon, Oct 19 • 12:00 PM

Aloma Cinema Grill

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Winter Park Institute Presents: A Conversation with José Andrés

Tue, Oct 20 • 5:30 PM

Warden Arena

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Ludicrous Speed Networking in Orlando · October · Winter Park Edition

Wed, Oct 28 • 11:00 AM

Winter Park Community Center

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4th Annual Florida Food is Medicine Symposium

Thursday • 8:00 AM

Center for Health and Wellbeing

Check ticket price on event

This Is How We Brunch | Brunch, Beats & Better Sundays

Sunday • 12:00 PM

Aroma Gastro Bar

Check ticket price on event

Environmental Advocacy Symposium

Fri, Oct 16 • 9:00 AM + 1 more

Barry University School of Law - Moot Courtroom

Check ticket price on event

Swing Swing with Steve Roman and his orchestra a tribute to Sammy Davis Jr

Fri, Oct 16 • 7:00 PM

Aloma Cinema & Grill

Check ticket price on event

Fall Jazz & Blues Concert

Sat, Oct 17 • 7:00 PM

Harry P Leu Gardens

Check ticket price on event

Free Movie for Seniors: Lucy Shimmers and the Prince of Peace

Mon, Oct 19 • 12:00 PM

Aloma Cinema Grill

Check ticket price on event

Winter Park Institute Presents: A Conversation with José Andrés

Tue, Oct 20 • 5:30 PM

Warden Arena

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Ludicrous Speed Networking in Orlando · October · Winter Park Edition

Wed, Oct 28 • 11:00 AM

Winter Park Community Center

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Online Events

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

Tomorrow • 7:30 PM GMT+1

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AI Kids Music Video Studio: Produce Black Nursery Rhyme for YouTube

Thursday • 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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(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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Lean Global Connection 2026

Thu, Nov 12 • 2:00 PM UTC

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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

Tomorrow • 7:30 PM GMT+1

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AI Kids Music Video Studio: Produce Black Nursery Rhyme for YouTube

Thursday • 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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(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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Lean Global Connection 2026

Thu, Nov 12 • 2:00 PM UTC

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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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Winter Park Romance & Roses Hunt

Friday • 4:00 PM + 8 more

251 S Park Ave

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Garden Blooms Beginner Glass Mosaic Workshop

Saturday • 10:00 AM

Harry P. Leu Gardens

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Kingdom Minded Innovative Academy: The Alabaster Jar

Saturday • 10:00 AM

Winter Park Community Center

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The R&B Brunch Sing-Along Oct 10th “Orlando “

Saturday • 12:00 PM

Aroma Gastro Bar

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Orlando Singles Event: Travel Trivia Night (Ages 30-45)

Saturday • 7:00 PM

480 Wine Bar

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Tai Chi in the Garden

Saturday • 10:30 AM

1300 S Denning Dr

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Fall 2026 Multiple Sclerosis Brunch and Silent Auction

Sunday • 1:00 PM

Winter Park Community Center

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This Is How We Brunch | Brunch, Beats & Better Sundays

Sunday • 12:00 PM

Aroma Gastro Bar

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Winter Park Romance & Roses Hunt

Friday • 4:00 PM + 8 more

251 S Park Ave

Check ticket price on event

Garden Blooms Beginner Glass Mosaic Workshop

Saturday • 10:00 AM

Harry P. Leu Gardens

Check ticket price on event

Kingdom Minded Innovative Academy: The Alabaster Jar

Saturday • 10:00 AM

Winter Park Community Center

Check ticket price on event

The R&B Brunch Sing-Along Oct 10th “Orlando “

Saturday • 12:00 PM

Aroma Gastro Bar

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Orlando Singles Event: Travel Trivia Night (Ages 30-45)

Saturday • 7:00 PM

480 Wine Bar

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Tai Chi in the Garden

Saturday • 10:30 AM

1300 S Denning Dr

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Fall 2026 Multiple Sclerosis Brunch and Silent Auction

Sunday • 1:00 PM

Winter Park Community Center

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This Is How We Brunch | Brunch, Beats & Better Sundays

Sunday • 12:00 PM

Aroma Gastro Bar

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Points of Interest near Winter Park

Mead Botanical Garden

Casa Feliz Historic Home Museum

Harry P Leu Gardens

Frequently asked questions about Winter Park

Are there any free events in Winter Park?

Yes, the city hosts several free public events. Popcorn Flicks in the Park offers free movie screenings in Central Park, and the annual Winter Park Sidewalk Art Festival transforms the main thoroughfare into an open-air gallery. These community gatherings are very popular.

Where can I find live music events?

The Blue Bamboo Center for the Arts is a key venue for eclectic music performances. For a different experience, Casa Feliz Historic Home Museum hosts a music series on select nights, and The Winter Park Playhouse often features cabarets alongside its mainstage shows.

What kinds of art events are popular in Winter Park?

Winter Park is known for its juried outdoor art festivals. The Winter Park Sidewalk Art Festival is a major annual event, while the Autumn Art Festival specifically showcases Florida artists. The Alfond Inn also features a contemporary art collection.

What are some date night ideas in Winter Park?

A stroll down Park Avenue offers many refined options for a date night. A classic evening could involve dinner at a fine dining restaurant, followed by a professional musical at The Winter Park Playhouse or a performance at the Annie Russell Theatre.

How can I find family-friendly things to do?

The city offers many activities suitable for families. The weekly Winter Park Farmers' Market is a great outing, and the Popcorn Flicks in the Park series provides free, family-friendly movie nights. The annual Christmas Parade is another local tradition.

Which neighborhoods are best for finding events?

Park Avenue is the central district for cultural events and festivals. This area is home to many galleries and is the site of major annual art events. Winter Park Village is another hub for entertainment, dining, and shopping.

Are there unique venues for special events?

Winter Park has several distinctive venues for hosting a special event. The Winter Park Events Center offers modern facilities with a ballroom and rooftop terrace, while the University Club of Winter Park provides a historic, Mediterranean-style setting for private functions.

What is the nightlife scene like in Winter Park?

Nightlife here is more centered on sophisticated dining and cultural experiences. The scene is focused on the sidewalk cafes and restaurants along Park Avenue, with evening entertainment often revolving around a show at a local theatre or a live music event.