Begin the evening at the Annual Holiday Tree Lighting in Central Park just east of the Winter Park train station. Local musicians will perform beginning at 5 p.m. Winners of the Holiday Art Competition will be recognized, Rabbi Dovid Dubov of Chabad Orlando will light the menorah to celebrate the sixth night of Chanukah, and Winter Park Mayor Phil Anderson will lead us in a countdown as we light the Christmas Tree. 

Diners and shoppers along Park Avenue will enjoy the smooth sounds of holiday jazz from 7 – 9 p.m. Be on the look out for entertainment along Park Avenue as the area becomes a pedestrian plaza for a festive street party.

A special guest from the North Pole will arrive at 6:30 p.m., thanks to the Winter Park Fire-Rescue Department. Santa and Mrs. Claus will be available for socially distanced visits and photos until 8:00 p.m.

We’re excited to announce that The Winter Park Chamber of Commerce will be sponsoring the Annual Holiday Art Competition in downtown Winter Park again this year.

The Holiday Art Competition winners will be announced Friday, Dec. 3, just prior to the lighting of the Christmas Tree (5:15 p.m.). Winners will also receive their gift certificates at that time.

The Holiday Art Competition is sponsored by Citizens Bank of Florida, Cogent Bank, First Citizens Bank, Seacoast Bank, and Winter Park National Bank. 

Popcorn Flicks in the Park, presented by the Enzian Theater and the Community Redevelopment Agency, will feature Frosty's Winter Wonderland beginning at 7 p.m., followed by The Santa Clause. Bring your own blanket or chairs to watch the movies, and pickup dinner from one of our local restaurants to enjoy a picnic in the park with your movie. 

Visitors can also enjoy free admission to the Charles Hosmer Morse Museum of American Art during Friday Nights at the Morse beginning at 4 p.m., as well as live music from 5 to 8 p.m..