Winter Park's 48th Christmas in the Park, the evening when the Morse Museum carries turn-of-the-century Tiffany windows out to Central Park and lights them while the Bach Festival Choir sings, is set for Thursday, December 3. It sits in the middle of a holiday calendar the City of Winter Park released on November 10 that runs from the day after Thanksgiving to a college marching band parade on December 28.
Most of it happens within a few blocks of Park Avenue and the Winter Park SunRail station, which the city points to as the simplest way in for the weeknight events.
The lights go up November 27
Downtown Winter Park switches on its holiday lighting on Friday, November 27. The city lists more than 20 wrapped trees along Park Avenue, a cathedral of lights in Central Park and a children's carousel that starts running the same day; the Park Avenue District handles the cathedral and the carousel.
On Saturday, November 28, the Parks and Recreation Department holds Light Up Seven Oaks at Seven Oaks Park from 5:30 to 8 p.m. The countdown to the digital Christmas tree starts at 6 p.m., followed by an outdoor screening of National Lampoon's Christmas Vacation.
Free Friday nights at the Morse
The Charles Hosmer Morse Museum of American Art on Park Avenue opens free on Friday nights through the season: November 27 and December 4, 11 and 18, from 4 to 8 p.m., with live music from 5 to 8 p.m. On Christmas Eve, admission is free from 9:30 a.m. to 4 p.m., with music from 1 to 4 p.m.
Christmas in the Park itself is a two-hour program starting at 6:15 p.m. on December 3, with the Bach Festival Choir, Brass Ensemble and Youth Choir on the main stage. Blankets and lawn chairs may go down in Central Park from 4 p.m.
The first weekend of December
The busiest stretch is December 4 to 6. On Friday, December 4, the Winter Park Chamber of Commerce and the city host Winter on the Avenue from 5 to 9 p.m., with the lighting of the city's Christmas tree in Central Park, a menorah lighting, a Kwanzaa kinara display, Santa and Mrs. Claus, carolers, snow slides and s'mores from Winter Park Fire-Rescue. The same night at 7 p.m., Enzian's Popcorn Flicks in the Park shows It's a Wonderful Life, preceded by Mickey's Christmas Carol.
Saturday, December 5, starts at 9 a.m. with the 74th Winter Park Chamber of Commerce Christmas Parade, running from Canton Avenue down Park Avenue to Lyman Avenue. Leadership Winter Park serves a pancake breakfast on the Central Park main stage from 7 to 10 a.m. for $7 a person, with proceeds going to leadership scholarships. That evening at 6:30 p.m., Chabad of Greater Orlando presents Chanukah on the Park in Central Park, with a stunt show, stilt walkers, live music and a Grand Menorah lighting.
On Sunday, December 6, at 6 p.m., the Orlando Philharmonic Orchestra plays a free Holiday Pops concert on the Central Park main stage.
On the water and around town
Firefighters open Station 61, at 343 W. Canton Ave., for a Santa Shift open house on Wednesday, December 9, from 5 to 7 p.m. Light Up Hannibal Square follows on Friday, December 11, from 6:30 to 8 p.m. outside the Hannibal Square Heritage Center, with a countdown at 6:45 p.m., free photos with Santa and a concert in Shady Park.
The Winter Park Holiday Boat Parade launches on Lake Virginia at 6 p.m. on Saturday, December 12, presented by the Winter Park Rotary Club. A watch party with music and treats starts at 5 p.m. at Dinky Dock Park, with bleachers and room for lawn chairs. Boat owners register through the parade's own site.
The Great American Big Band plays the Central Park main stage at 7 p.m. on Friday, December 18. The Merry Tuba Concert, a free performance by tuba, euphonium, sousaphone and baritone players of all ages, is at 1 p.m. on Saturday, December 19; musicians register at 9 a.m. and rehearse at 10 a.m. The Equity Council Corp. holds its Kwanzaa Celebration at the Winter Park Community Center on Saturday, December 26, from 5 to 9 p.m.
The season closes on Monday, December 28, at 3:30 p.m., when college bands march through downtown for the Pop-Tarts Bowl Parade of Bands and play a preview in Central Park ahead of the bowl game at Camping World Stadium the next evening.
Plan ahead
Many of these events close streets around Park Avenue, and the city posts each closure on its Closures and Construction page. Central Park sits beside the Winter Park SunRail station, and the city keeps a parking page for planning ahead. The full lineup is at cityofwinterpark.org/holiday-events.

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