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  • December 3, 2021 | 5:00 PM - 9:00 PM | Central Park, Park Avenue, Winter Park


    Kick Off the Holidays in Winter Park


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  • Winter On The Avenue is from 5:00 p.m. – 9:00 p.m. on December 3rd. Come out for our annual tree-lighting, strolling carolers, jazz on Park Avenue, the announcement of holiday art contest winners, and, of course, Santa Claus. Masks and social distancing are among the safety measures to be in place.

  • Holiday Tree Lighting Holiday Tree Lighting

    Begin the evening at the 27th 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 also be recognized and Winter Park Mayor, Steve Leary, will lead us in a countdown as we light the Christmas Tree.

    Music and Entertainment Music and Entertainment

    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.

  • Visit and Photo with Santa Visit and Photo with Santa

    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.

    Holiday Art Competition Holiday Art Competition

    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 held Friday, Dec. 3 just prior to the lighting of the Holiday Tree of Lights (5:15 p.m.). Winners will also receive their gift certificates at that time.


    This event is free and open to the public.