• Winter-on-the-Avenue-Logo-1.png

    December 4 | 5:30 PM - 9:30 PM | Central Park, Park Avenue, Winter Park


    Presented by:


    Supported by:





    Kickoff the holidays in Winter Park

    Join in the tradition of Winter Park holiday festivities as Park Avenue is transformed into a winter wonderland, complete with a tree lighting, carolers, and a visit from Santa. The Winter Park Chamber of Commerce has partnered with the City of Winter Park, Park Avenue Merchants Association, and Enzian Theater to kickoff the holidays in Winter Park the first Friday evening in December.

    Be part of this tradition as Park Avenue is transformed into a winter wonderland for a holiday street party.

    Come experience the best of downtown Winter Park this holiday season! Park Avenue will be closed to vehicular traffic in order to transform downtown into a pedestrian plaza, beginning at 2 p.m. New England Avenue will remain open to thru traffic.


    This event is free and open to the public.


  • A flurry of activities will be held from 5:30 p.m. - 9:30 p.m. including:

  • 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 children’s choirs 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. Complimentary refreshments from local merchants will also be available.

    Music and Entertainment Music and Entertainment

    Diners and shoppers along Park Avenue will enjoy the smooth sounds of holiday jazz from 7 – 10 p.m. Be on the look out for entertainment along Park Avenue as the area becomes a pedestrian plaza for a festive street party.

  • Popcorn Flicks in the Park Popcorn Flicks in the Park

    Popcorn Flicks in the Park, presented by Enzian Theater and the Community Redevelopment Agency, will feature How The Grinch Stole Christmas (1966) beginning at 7 p.m., followed by Elf

    Friday Night at the Morse Museum Friday Night at the Morse Museum

    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. A special curator tour of Louis Comfort Tiffany’s Laurelton Hall begins at 7 p.m.

  • 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 visits and photos until 8:00 p.m., along with complimentary refreshments from local merchants.

    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 competition is open to children 13 years of age and younger. There are two categories, ages 7 and younger and ages 8 to 12. Two winners per category will be presented with $100 gift cards. An official entry form is enclosed, which may be reproduced as needed by school art departments, art clubs and organizations.

    Please check back later in the year for the applications.

    This year’s winning artwork will be scanned and printed on holiday banners that will be displayed along the light poles around the City of Winter Park. The unveiling of the Holiday Art Competition winners will be held Friday, Dec. 1 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.