Winter Park Christmas Events

Candlelight: Christmas Carols on Strings - Orlando

1300 S Denning Dr, Winter Park, FL 11 Dec 2025

Community Shred Event (and Toy & Food Drive)

Nelson Financial Planning 4 Dec 2025

A Magical Brunch with Santa at The Alfond Inn

The Alfond Inn at Rollins College 7 Dec 2025

Free for Seniors: The Best Christmas Pageant Ever

Aloma Cinema Grill 16 Dec 2025

A Jazzy Christmas

Blue Bamboo Center For The Arts 6 Dec 2025

Journey to Bethlehem | Christmas Musical

1815 State Road 436, Winter Park, FL, United States, Florida 32792 7 Dec 2025

Free Movie for Seniors: The Holdovers

Aloma Cinema Grill 9 Dec 2025

Christmas Swing Dance

6904 Aloma Ave, Winter Park, FL 32792-7003, United States 13 Dec 2025

Christmas on The Avenue (SOLD OUT)

402 Welborne Ave, Winter Park, FL 32789-4216, United States 23 Nov 2025

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

Aloma Cinema Grill 14 Dec 2025

Annual San Pedro Center Christmas Celebration!

95 Bishop Grady Lane, Winter Park, FL, United States, Florida 32792 17 Dec 2025

The Best Christmas Pageant Ever

Shaeffer Hall at St. John Church 12 Dec 2025

47th Annual Christmas in the Park

Central Park 251 Park Avenue South, Winter Park, FL 32789 4 Dec 2025

A Christmas Romance Tour with Marcus Anderson & Rebecca Jade

460 E. New England Ave., Winter Park, FL, United States, Florida 32789 19 Dec 2025

Derby on Park (Kentucky Derby Party)

Winter Park Events Center 2 May 2026

Happy Hour Tour at The Alfond Inn / December

The Alfond Inn at Rollins College 3 Dec 2025

Last Show of the Year for Human Clay at Conduit!!!

Conduit 26 Dec 2025

Yule Be Sorry You Asked

Shaeffer Hall at St. John Church 13 Dec 2025

Christmas on The Avenue (SOLD OUT)

402 Welborne Ave, Winter Park, FL 32789-4216, United States 22 Nov 2025

A Classic Christmas

Knowles Memorial Chapel 13 Dec 2025

Christmas on The Avenue (SOLD OUT)

402 Welborne Ave, Winter Park, FL 32789-4216, United States 30 Nov 2025

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

Wesh 2 News 12 Dec 2025

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

Winter Park Ballroom Dance Co. 14 Dec 2025

2025 Osceola Christmas Parade presented by Osceola Main Street

Downtown Osceola 9 Dec 2025

NRG Dance Country Christmas Winter Showcase

Winter Park Events Center 16 Dec 2025

5th Annual Christmas Ham Shoot-out!

Trick Shots Winter Park 27 Dec 2025

Watercolor & Wine

Albin Polasek Museum & Sculpture Gardens 21 Nov 2025

Roberto Coin Trunk Show

152 South Park Avenue, Winter Park, FL, United States, Florida 32789 4 Dec 2025

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

150 N New York Ave Winter Park, FL 32789, USA 13 Dec 2025