Winter Park Holiday Events

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

A Jazzy Christmas

Blue Bamboo Center For The Arts 6 Dec 2025

Rollins College Employee Holiday Support

Rollins College 21 Nov 2025

2025 Poinsettia Giveaway + Holiday Party

Winter Park Events Center 11 Dec 2025

Flow for Tots- Charity Class

Winter Park Yoga 13 Dec 2025

Small Biz Saturday Sip and Shop

Cami Monet 29 Nov 2025

Fabio’s Table: European Holiday Traditions

444 West New England Avenue - Suite 119, Winter Park, FL, United States, Florida 32789 27 Dec 2025

Free Movie for Seniors: The Holdovers

Aloma Cinema Grill 9 Dec 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 23 Nov 2025

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

Aloma Cinema Grill 14 Dec 2025

Holidays in the Park

Woman's Club of Winter Park, Inc. 6 Dec 2025

Advent Wreath Workshop

All Saints Episcopal Church 30 Nov 2025

Thanksgiving Weekend Celebration

445 N Park Ave, Winter Park, FL, United States, Florida 32789 30 Nov 2025

The Best Christmas Pageant Ever

Shaeffer Hall at St. John Church 12 Dec 2025

Soup Opera

St. John Lutheran Church 6 Dec 2025

The Santa Shift

Winter Park Fire-Rescue Department 10 Dec 2025

USBC Orlando Regional presents Baby DJ Holiday Toy Drive

Aloma Bowling Center 6 Dec 2025

Vegan Thanksgivng Potluck- Winter Park

Shady Park 22 Nov 2025

Sip and Shop for SCAC & the Arts in Seminole County!

460 N Orlando Ave, Winter Park, FL 32789, United States 21 Nov 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

SCRUBS SOCIAL

1685 Lee Rd 5 Dec 2025

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

Conduit 27 Dec 2025

Holiday Boat Parade Paddle & Toy Drive

Dinky Dock Park 13 Dec 2025

Thanksgiving Weekend Celebration

445 N Park Ave, Winter Park, FL, United States, Florida 32789 29 Nov 2025

Ladies Night at Boca | Holiday Edition

358 N Park Ave 20 Nov 2025

Private Holiday Party

Winter Park Fl 6 Dec 2025

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

Conduit 14 Dec 2025

Yule Be Sorry You Asked

Shaeffer Hall at St. John Church 13 Dec 2025

Fiddler’s Welcomes Back Willy & The Pour Boys

Fiddler's Green Irish Pub & Eatery 30 Nov 2025

Christmas on The Avenue (SOLD OUT)

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

Giving Tuesday Shop & Share at Winter Park Village

Winter Park Village 2 Dec 2025

Charity Nine & Wine Golf Fundraiser & Annual Holiday Party

Winter Park Golf Course 3 Dec 2025

Takodana End of Year Awards Dinner

Miller's Ale House (Winter Park Village) 22 Nov 2025

Christmas on The Avenue (SOLD OUT)

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

The Nutcracker: Presented by Apopka Dance Center

Annie Russell Theatre 20 Dec 2025

CFBAA Holiday Party 2025!

Ravenous Pig 10 Dec 2025

Ladies Relax & Recharge Lunch (Winter Park)

Garp & Fuss 13 Dec 2025

Polasek Nights – A Holiday Speakeasy

Albin Polasek Museum & Sculpture Gardens 10 Dec 2025

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

6904 Aloma Ave, Winter Park, FL 32792-7003, United States 6 Dec 2025

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

Wesh 2 News 12 Dec 2025

Kwiat | Fred Leighton Holiday Trunk Show

152 South Park Avenue, Winter Park, FL, United States, Florida 32789 12 Dec 2025

Holiday Cheer- A Central Florida CRE Holiday Event!

Winter Park Events Center 2 Dec 2025

Sugar Plum Soirée

Annie Russell Theatre 21 Dec 2025

Thanksgiving Harvest Celebration Brunch Buffet at The Alfond Inn

The Alfond Inn at Rollins College 27 Nov 2025

CHANGE OF PLANS / Shut Down Bounce Back: Winter Park Farmer's Market & Park SATURDAY instead of Fri!

Winter Park Farmers’ Market 29 Nov 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

Thanksgiving Weekend Celebration

445 N Park Ave, Winter Park, FL, United States, Florida 32789 28 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