Holiday events in Winter Park

Check out happening holiday events all around Winter Park, FL

GROWvember Fall Plant Sale

 Fri, 07 Nov at 02:00 pm Mead Botanical Garden Free

Community Shred Event (and Toy & Food Drive)

 Thu, 04 Dec at 09:00 am Nelson Financial Planning Free

The Best Christmas Pageant Ever

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

Mix & Mingle: A Jewelry Social

 Thu, 13 Nov at 06:30 pm Penthouse 450 Free

A “Not So Silent Night” featuring Withering Earth Saturday December 27th, 2025!

 Sat, 27 Dec at 07:00 pm Conduit

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

Yule Be Sorry You Asked

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

Holiday Classic Mini Session (SOLD OUT)

 Sat, 08 Nov at 03:00 pm Hannibal Square

Polasek Nights – A Holiday Speakeasy

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

Pre Black Friday Flash Sale

 Fri, 07 Nov at 08:00 am 2828 Casa Aloma Way suite 300 Free

Vegan Thanksgivng Potluck- Winter Park

 Sat, 22 Nov at 02:00 pm Shady Park

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

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

Tinker Time

 Sun, 16 Nov at 02:00 pm 721 W New England Ave Free

Christmas Minis

 Sat, 08 Nov at 12:00 am Lake Baldwin Park

USBC Orlando Regional presents Baby DJ Holiday Toy Drive

 Sat, 06 Dec at 06:00 pm Aloma Bowling Center

Fiddler’s Welcomes Back Willy & The Pour Boys

 Sun, 30 Nov at 05:00 pm Fiddler's Green Irish Pub & Eatery

A Classic Christmas

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

Christmas on The Avenue (ONE SPOT)

 Sat, 22 Nov at 03:30 pm 402 Welborne Ave, Winter Park, FL 32789-4216, United States

EXHIBITION TOUR | Portrait of a Movement: A New Approach to the Bloomsbury Group

 Fri, 14 Nov at 11:00 am Rollins Museum of Art

Christmas on The Avenue (SOLD OUT)

 Sun, 23 Nov at 03:30 pm 402 Welborne Ave, Winter Park, FL 32789-4216, United States

Christmas on The Avenue (SOLD OUT)

 Sun, 30 Nov at 03:30 pm 402 Welborne Ave, Winter Park, FL 32789-4216, United States

CFBAA Holiday Party 2025!

 Wed, 10 Dec at 05:00 pm Ravenous Pig

Holiday Showcase & Mini-Match Winter Park Ballroom with Adj. Larry Dean

 Sat, 06 Dec at 11:00 am 6904 Aloma Ave, Winter Park, FL 32792-7003, United States

Holiday Boat Parade Paddle & Toy Drive

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

Thanksgiving Harvest Celebration Brunch Buffet at The Alfond Inn

 Thu, 27 Nov at 11:00 am The Alfond Inn at Rollins College USD 0 to 159

Kwiat | Fred Leighton Holiday Trunk Show

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

Fairy Hair Fun at the Commons CO-OP Local Market ~ Winter Park

 Wed, 05 Nov at 03:00 pm Center for Health & Wellbeing

Roberto Coin Trunk Show

 Thu, 04 Dec at 10:00 am 152 South Park Avenue, Winter Park, FL, United States, Florida 32789

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