- December 18, 2025
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NOV. 28
Each year on Thanksgiving morning, thousands of participants come out for the Turkey Trot, a 5K (3.1 miles) run/power walk and Tot Trot to benefit Seniors First. Last year, the race drew more than 5,600 participants to downtown Orlando’s Lake Eola. Runners of all ages and levels are encouraged to attend. Seniors First is a nonprofit social service organization dedicated to serving the needs of Central Florida’s elderly population with a broad spectrum of nutrition, home improvement and support services. The funds raised as a result of the Turkey Trot directly benefit the seniors of Orange and Seminole counties. Costume judging begins at 7 a.m. so get there early on Thanksgiving! Visit turkeytrotorlando.com for more information.
DEC. 4-7
The Rotary Club Tip-Off Classic Invitational high school basketball tournament is where potential future NBA stars play, and college and pro scouts congregate. The tournament will be held at the Winter Park High School Gymnasium, 2100 Summerfield Road, Winter Park. It starts at 7 p.m. on Wednesday, Dec. 4, and runs through Saturday, Dec. 7, with the final game being played at 8:30 p.m. This tournament has raised more than $925,000 for charities, the participating schools, and $12,000 college scholarships to deserving “B” students who could not otherwise afford to attend college. Admission into the tournament is $5 or two cans of food.
DEC. 7
Maitland’s “Season of Light” Saturday, Dec. 7, at 3 p.m. is a longstanding tradition in our community and we invite you to join us in our holiday celebration. It’s an excellent opportunity to make new holiday memories and share the spirit of the season with family, friends and loved ones. You may even run into Santa Claus! You are invited to stroll around Lake Lily Park, enjoy gift vendors open for early shopping, and snack at local food trucks including Yum Yum Cupcake, Midnight Sun Ice cream Sandwich Company, All Things Sweet, Tucks Table, and The Big Cheese. The show begins at 3 p.m. with live stage entertainment by the “Outer Toons,” the School of Performing Arts Dancers and strolling entertainment. There will be a tree lighting, Santa Claus, and a fireworks finale.
Winter Park’s 61st annual Ye Olde Hometown Christmas Parade hits Park Avenue at 9 a.m. on Dec. 7, heading south from Cole Avenue alongside Central Park and ending at Lyman Avenue.
ONGOING
Now through Sunday, Jan. 5, the city of Winter Park is bundling up once again for “Winter in the Park,” the city’s annual holiday ice skating rink in Central Park West Meadow. The West Meadow is located at 150 N. New York Ave., on the corner of New York Avenue and Morse Boulevard, in downtown Winter Park. Snowflakes of all ages and skill levels are invited to chill out as they glide, spin and turn at “Winter in the Park.” Visit cityofwinterpark.org for more information.