Annual Longwood Luau Sat, 07 Nov at 04:00 pm 3592 Aloma Ave Suite 2, Winter Park, FL, United States, Florida 32792 ART
Florida Blue's Winter Wonderland - FREE Toy Giveaway Fri, 04 Dec at 05:00 pm Florida Blue Center - Orlando FREE CHRISTMAS
Twelve Sips of Christmas — Holiday Cocktail Making Class Tue, 15 Dec at 05:30 pm The Alfond Inn at Rollins College USD 64 HOLIDAY
Holiday Eggnog & Ugly Sweaters Sat, 19 Dec at 03:30 pm The Alfond Inn at Rollins College USD 32 FITNESS
Winter Park Murder Mystery 2: Crime on Date Night! Sun, 01 Nov at 12:00 am Winter Park Historical Association USD 15 TRIPS-ADVENTURES
Winter Park Murder Mystery: Solve the case! Sun, 01 Nov at 12:00 am Peacock Fountain USD 10 TRIPS-ADVENTURES
Michael Andrew & Ray Gelato | November 20 | Blue Bamboo Fri, 20 Nov at 08:00 pm Blue Bamboo Center For The Arts MUSIC
Gingerbread at The Alfond Inn Sun, 20 Dec at 03:00 pm The Alfond Inn at Rollins College USD 47 FITNESS
The Porch in Winter Park, Florida - Doc Probes - Beach & Buffett Thu, 12 Nov at 05:30 pm The Porch Winter Park PARTIES
Groove Sleighers Christmas Show | November 28 | Blue Bamboo Sat, 28 Nov at 08:00 pm 460 E. New England Ave., Winter Park, FL, United States, Florida 32789 CHRISTMAS
Merry Mornings & Coffee: A Tasting Experience with Artifx Cafe Coffee Fri, 18 Dec at 09:00 am The Alfond Inn at Rollins College USD 29 FITNESS
Winter Park Magazine's 2026 Most Influential Thu, 12 Nov at 05:30 pm Winter Park Farmers' Market Venue USD 55 TO 535 FITNESS
The Group Chat Presents: Episode 11/15 — The Soft Launch Sun, 15 Nov at 03:00 pm Momentun Creative studio USD 27 FITNESS
Matt-n-Cammie's 20th Anniversary Party Fri, 04 Dec at 07:00 pm 6700 Aloma Ave, Winter Park, FL 32792-6801, United States ENTERTAINMENT
RSVLTS - Avengers: Doomsday Premiere Event Thu, 17 Dec at 08:00 pm Aloma Cinema Grill USD 116 FITNESS
2026 San Pedro Center Christmas Celebration! Wed, 16 Dec at 06:00 pm 95 Bishop Grady Lane, Winter Park, FL, United States, Florida 32792 MUSIC
Orlando Renaissance Faire Sun, 06 Dec at 10:00 am Southport Community Park 3505 E Landstreet Orlando FL, 32827 WORKSHOPS
6th Annual Kid$ Bi$ Children Business Fair Sat, 19 Dec at 10:00 am 150 N New York Ave, Winter Park, FL 32789-3116, United States BUSINESS
The Charles Hosmer Morse Museum - Sunrail Adventure Sat, 23 Jan at 09:00 am The Charles Hosmer Morse Museum of American Art TRIPS-ADVENTURES
Peace Breakfast: An Interfaith and Worldview Gathering Thu, 12 Nov at 08:45 am Rice Family Pavilion FREE FITNESS
AdventHealth Run 4 Love 4 Mile Sat, 13 Feb at 07:30 am 250 Perth Ln, Winter Park, FL 32792, United States KIDS
Fresh Start, New Friends: Women’s Open Friendship Table (Winter Park) Wed, 20 Jan at 06:30 pm S Orlando Ave, Winter Park, FL 32789, United States MEETUPS
3rd Annual Winter Park YMCA Car Show Sat, 06 Mar at 09:00 am 1201 N Lakemont Ave, Winter Park, FL 32792
A Steve Roman production - Noche Latina LP Latin Power Sat, 13 Mar at 07:00 pm Aloma Cinema & Grill USD 30 TO 42 FITNESS
Friendsgiving Paint Party (Winter Park) Thu, 19 Nov at 06:00 pm 229 W Fairbanks Ave, Winter Park, FL 32789-4392, United States
Heart and Harmony: Living Well With HCM Thu, 19 Nov at 10:00 am Center for Health & Wellbeing HEALTH-WELLNESS
Orlando Zine Fest 2026 Sat, 12 Dec at 07:00 pm Gardens, 1938 W Fairbanks Ave, Winter Park, FL FESTIVALS
10th Annual Holiday Bridge Tournament (Canasta & Mahjong, too!) Fri, 04 Dec at 10:30 am Interlachen Country Club (2245 Interlachen Court, Winter Park, FL 32792) SPORTS