Holiday events in Winter Park

Check out happening holiday events all around Winter Park, FL

The Nutcracker: Presented by Apopka Dance Center

Sat, 20 Dec at 01:30 pm Annie Russell Theatre

A Magical Brunch with Santa at The Alfond Inn

 Sun, 07 Dec at 10:00 am The Alfond Inn at Rollins College USD 0 to 70

lululemon members' Holiday Shop at Winter Park

 Sun, 14 Dec at 06:00 pm lululemon Free

Free Movie for Seniors: The Holdovers

 Tue, 09 Dec at 12:00 pm Aloma Cinema Grill Free

Winter Park Village Holiday Concert Series

 Tue, 09 Dec at 06:00 pm Winter Park Village

Season's Greetings from the Garden

 Sun, 14 Dec at 02:00 pm 1300 S Denning Dr, Winter Park, FL

Polasek Nights – A Holiday Speakeasy

 Wed, 10 Dec at 06:00 pm Albin Polasek Museum & Sculpture Gardens USD 23 to 29

Free Foxtail Friday!

 Fri, 12 Dec at 11:00 am Foxtail Coffee (Winter Park, FL)

CFBAA Holiday Party 2025!

 Wed, 10 Dec at 05:00 pm Ravenous Pig

Kwiat | Fred Leighton Holiday Trunk Show

 Fri, 12 Dec at 10:00 am 152 South Park Avenue, Winter Park, FL, United States, Florida 32789

The Best Christmas Pageant Ever

 Fri, 12 Dec at 07:00 pm Shaeffer Hall at St. John Church

Holiday Boat Parade Paddle & Toy Drive

 Sat, 13 Dec at 05:00 pm Dinky Dock Park USD 34 to 61

A Christmas Romance Tour with Marcus Anderson & Rebecca Jade

 Fri, 19 Dec at 08:00 pm 460 E. New England Ave., Winter Park, FL, United States, Florida 32789

2025 Poinsettia Giveaway + Holiday Party

 Thu, 11 Dec at 06:00 pm Winter Park Events Center Free

Holiday Pops in Winter Park

 Sat, 13 Dec at 06:00 pm Central Park in Winter Park 251 South Park Avenue Winter Park , FL 32789

Holiday Music featuring Magic of Bronze with the Mudita Collective Ensemble

 Fri, 12 Dec at 07:30 pm John M. Tiedtke Concert Hall USD 29 to 34

Fabio’s Table: European Holiday Traditions

Sat, 27 Dec at 05:45 pm 444 West New England Avenue - Suite 119, Winter Park, FL, United States, Florida 32789

Peppermint Latte Party at Cami Monet

 Sat, 13 Dec at 10:00 am 1801 Oglesby Avenue, Winter Park, FL, United States, Florida 32789

Flow for Tots- Charity Class

 Sat, 13 Dec at 12:00 pm Winter Park Yoga Free

Yule Be Sorry You Asked

 Sat, 13 Dec at 03:00 pm Shaeffer Hall at St. John Church

A Classic Christmas

 Sat, 13 Dec at 01:00 pm Knowles Memorial Chapel

DIRTY ROTTEN IMBECILES ARE BACK AT IT!! Sunday 12/14 at Conduit!!!

 Sun, 14 Dec at 07:00 pm Conduit

The Santa Shift

Wed, 10 Dec at 05:00 pm Winter Park Fire-Rescue Department

Ladies Relax & Recharge Lunch (Winter Park)

 Sat, 13 Dec at 11:30 am Garp & Fuss

No Doubt Gwen Stefani Holiday Tribute & Toys for Tots at Aloma Cinema Grill

 Sun, 14 Dec at 06:00 pm Aloma Cinema Grill USD 25 to 36

Holidays Around The World

 Sat, 13 Dec at 10:00 am 2500 Cady Way, Winter Park, FL

Winter Market

 Sun, 07 Dec at 01:00 pm Albin Polasek Museum & Sculpture Gardens Free

Share Your Christmas 2025 | 40th annual WESH 2 Food Drive

 Fri, 12 Dec at 06:00 am Wesh 2 News

Be On Park Holiday Trunk Shows

 Fri, 19 Dec at 10:00 am 152 South Park Avenue, Winter Park, FL

Sugar Plum Soirée

 Sun, 21 Dec at 11:30 am Annie Russell Theatre

Live Band Sunday! 1 Hour Special Rumba Class + Dennie & the Jets 2 hours of dancing $18 cover

Sun, 14 Dec at 02:00 pm Winter Park Ballroom Dance Co.

5th Annual Kid$ Bi$ Children's Business Fair Orlando, Florida

 Sat, 13 Dec at 09:00 am 150 N New York Ave Winter Park, FL 32789, USA