Winter on the Avenue

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, snowmaking, 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 on Friday, December 1, 2017. 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 3 p.m. New England Avenue will remain open to thru traffic.

A flurry of activities will be held from 5 – 10 p.m., including:

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 former WFTV Channel 9 news anchor Bob Opsahl will join the crowd for the lighting of the Tree of Lights. Complimentary refreshments from local merchants will also be available.

Visits and Photos 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.

Popcorn Flicks in the Park

Popcorn Flicks in the Park, presented by Enzian Theater and the Community Redevelopment Agency, will show the animated classic “How the Grinch Stole Christmas” will begin at 7 p.m., followed by the feature film, “A Muppet Family Christmas”

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.

Merchant Open House & Window Contest

The Park Avenue Merchants Association will host its annual holiday open house from 5 to 8 p.m., or later, at participating locations. Shoppers can stroll along Park Avenue and area side streets to admire the globes of light, enjoy festive refreshments, shop with local merchants and vote in the Winter on the Avenue Holiday Window Contest through a simple text-to-vote system.

Winter in the Park Holiday Ice Skating Rink

Throughout the evening, the city’s “Winter in the Park” holiday ice skating rink will be open for skaters of all ages to whirl and twirl for $13 per skater (skate rental included). The rink is located at the corner of Morse Boulevard and New York Avenue.

Friday Nights at the Morse

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.

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 13. 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 note the deadline for submission is 5 p.m. Friday, Nov. 17 and judging will take place Monday, Nov. 20.

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.

Holiday Art Contest Submission Form


For additional information about this event, including vendor opportunities, sponsorship or the holiday art competition, contact Ally Stricker at or call (407) 644-8281.

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