Best Entertainment events in Winter Park December 2025

Q: What are the upcoming Entertainment events in Winter Park, FL?

Here are the upcoming events in Winter Park, FL: Free Movie for Seniors: Avatar Fire and Ash, Holiday Brunch with Live Music & Cajun Cuisine, MamboYá Social, IRONING / NO FACE / UNFADE, Jeff Rupert Quartet at Blue Bamboo, Holidays Orlando Chicago Bears Game Day Party

Q: Which kind of events are trending in Winter Park, FL?

Here are the top trending events in Winter Park, FLFestivals, Free Events, 🥂 New Year, Car Shows, Live Music

Entertainment events in Winter Park in December

Tue, 30 Dec, 2025 - 12:00 PM

Free Movie for Seniors: Avatar Fire and Ash

Aloma Cinema Grill

8+ Interested

|

Free
Sun, 28 Dec, 2025 - 11:00 AM

Holiday Brunch with Live Music & Cajun Cuisine

Tibby's New Orleans Kitchen

Free
Sun, 28 Dec, 2025 - 05:00 PM

MamboYá Social

The Trap

42+ Interested
Fri, 26 Dec, 2025 - 06:30 PM

IRONING / NO FACE / UNFADE

2902 Ambergate Road, Winter Park, FL, United States, Florida 32792

17+ Interested
Ongoing

Jeff Rupert Quartet at Blue Bamboo

Blue Bamboo Center For The Arts
Sun, 28 Dec, 2025 - 08:15 PM

Holidays Orlando Chicago Bears Game Day Party

Friendly Confines, Winter Park

13+ Interested

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Sat, 14 Mar • 07:30 PM

🎸❤️TOTALLY TOM PETTY LAS VEGAS SHOW in FLORIDA - SAT March 14, 2026

Mount Dora Music Hall

67+ Interested

|

USD 37
Sat, 10 Jan Onwards

Sip, Stroke & Whine Paint Party

Napasorn Thai Restaurant

19+ Interested

|

Free
Sat, 27 Dec Onwards

Melbourne Beach Scavenger Hunt For Couples - SHOW LOVE (Date Night!!)

Recommended scavenger starting point or other city spot of your choice! (YOU MUST USE PDF TICKETS EMAILED FOR EVENT- NO MOBILE APP OR QR CODES ACCEPTED)

Newly Added

|

USD 10
Sat, 14 Feb • 03:30 PM

Lover's & Friends Bahamas Cruise 2026

Port Canaveral

83+ Interested

|

USD 50
Sat, 27 Dec Onwards

Rock Hard Revue | The #1 Male Revue in Florida

Rock Hard Revue

6+ Interested

|

USD 20
Sat, 27 Dec Onwards

Kissimmee Scavenger Hunt For Couples - SHOW LOVE (Date Night!!)

Recommended scavenger starting point or other city spot of your choice! (YOU MUST USE PDF TICKETS EMAILED FOR EVENT- NO MOBILE APP OR QR CODES ACCEPTED)

Newly Added

|

USD 10
Sat, 27 Dec Onwards

Clermont Scavenger Hunt For Couples - SHOW LOVE (Date Night!!)

Recommended scavenger starting point or other city spot of your choice! (YOU MUST USE PDF TICKETS EMAILED FOR EVENT- NO MOBILE APP OR QR CODES ACCEPTED)

Newly Added

|

USD 10
Wed, 21 Jan • 07:30 PM

Diana Krall at King Center for the Performing Arts

King Center for the Performing Arts
Thu, 22 Jan • 12:30 AM

Diana Krall

Maxwell C. King Center for the Performing Arts

Frequently Asked Questions

Which Entertainment events can I attend in Winter Park, FL this weekend?

Here are the best Entertainment events happening in Winter Park, FL this weekend:

Holiday Brunch with Live Music & Cajun Cuisine is happening on Sun 28 Dec 2025 from 11:00 AM onwards at Tibby's New Orleans Kitchen, Winter Park, FL
MamboYá Social is happening on Sun 28 Dec 2025 from 5:00 PM onwards at The Trap, Winter Park, FL
Holidays Orlando Chicago Bears Game Day Party is happening on Sun 28 Dec 2025 from 8:15 PM onwards at Friendly Confines, Winter Park, Winter Park, FL

What are the upcoming Entertainment events in Winter Park, FL?

Here are the upcoming Entertainment events in Winter Park, FL:

Free Movie for Seniors: Avatar Fire and Ash is happening on Tue 30 Dec 2025 from 12:00 PM onwards at Aloma Cinema Grill, Winter Park, FL
Holiday Brunch with Live Music & Cajun Cuisine is happening on Sun 28 Dec 2025 from 11:00 AM onwards at Tibby's New Orleans Kitchen, Winter Park, FL
MamboYá Social is happening on Sun 28 Dec 2025 from 5:00 PM onwards at The Trap, Winter Park, FL
IRONING / NO FACE / UNFADE is happening on Fri 26 Dec 2025 from 6:30 PM onwards at 2902 Ambergate Road, Winter Park, FL, United States, Florida 32792
Jeff Rupert Quartet at Blue Bamboo is happening on Fri 26 Dec 2025 from 8:00 PM onwards at Blue Bamboo Center For The Arts, Winter Park, FL
Holidays Orlando Chicago Bears Game Day Party is happening on Sun 28 Dec 2025 from 8:15 PM onwards at Friendly Confines, Winter Park, Winter Park, FL

Which kind of events are trending in Winter Park, FL?