At 4 p.m. on Thursday, December 3, blankets and lawn chairs start going down on the north end of Central Park, near Garfield and Park avenues. Seven leaded-glass windows by Tiffany will already be up by then. Tables are not allowed. The windows light at 6:15. By 8:30 they go dark, and they won't be back on that lawn until next December.
Twenty-four hours later, the same park has a different organizer and a different focal point. The rules change too. By Saturday morning the action has moved onto Park Avenue itself. On Saturday night it returns to the lawn under a third host. Winter Park's first weekend of December can feel like a single festival, but the five events on its calendar belong to three lead hosts: the Morse Museum, the Winter Park Chamber of Commerce and Chabad of Greater Orlando, with partners such as the City and the Enzian Theater joining in. Each one decides where its crowd gathers, when the evening starts and what you should bring.
The Weekend at a Glance
| Day | Event | Host | Time | Where |
|---|---|---|---|---|
| Thu, Dec. 3 | 48th Christmas in the Park | Morse Museum and City of Winter Park | 6:15–8:30 p.m. | North Central Park, near Garfield and Park avenues |
| Fri, Dec. 4 | Winter On the Avenue | Winter Park Chamber of Commerce | 5–9 p.m. | Central Park and Park Avenue |
| Fri, Dec. 4 | Popcorn Flicks: It's a Wonderful Life | Enzian Theater and the Community Redevelopment Agency | 8 p.m. | Central Park |
| Sat, Dec. 5 | 74th Ye Olde Hometown Christmas Parade | Winter Park Chamber of Commerce | 9–10:30 a.m. | Park Avenue, Cole Avenue to Pennsylvania Avenue |
| Sat, Dec. 5 | Chanukah on the Park | Chabad of Greater Orlando | 6:30 p.m. | Central Park |
All five are free. The differences are in the details below.
Thursday Belongs to the Morse, and It Runs on a Concert Clock
Christmas in the Park opens the weekend. According to the Charles Hosmer Morse Museum of American Art, it began in 1979. Jeannette Genius McKean and Hugh F. McKean created it as a way to share their Tiffany collection with the public. This year is the 48th, presented by the Museum together with the City of Winter Park.
The seven windows displayed outdoors have a history of their own. The Museum describes them as religious memorials made for the chapel of a charitable residence in New York. The McKeans acquired them in 1974, when that building faced demolition. They are set up about a block from the Museum. That puts the evening on the north end of the park, away from the train station side.
The schedule is built around music. The Bach Festival Society Choir and Brass Ensemble perform holiday favorites. The Museum's timeline looks like this:
- 4 p.m.: Blankets and lawn chairs may be set up once the windows are installed
- 6:15 p.m.: Windows light
- About 8 p.m.: Concert ends
- 8:30 p.m.: Windows go dark
Thursday is a seated evening, so the 4 p.m. setup time matters. With tables off the lawn, the evening is set up for sitting and listening to the concert.
Friday Shifts to the Train Station and Turns Park Avenue Into a Plaza
On Friday, December 4, the Winter Park Chamber of Commerce takes over for Winter On the Avenue, 5 to 9 p.m. The center of the evening moves to the annual Holiday Tree Lighting in Central Park, just east of the Winter Park train station.
The Chamber has planned a full program around the lighting. Winners of the Holiday Art Competition are recognized. Rabbi Dovid Dubov of Chabad Orlando leads a menorah lighting to begin the Chanukah season. Mayor Sheila DeCiccio then leads the countdown to light the Christmas tree.
Friday also spreads out much further than Thursday. Park Avenue becomes a pedestrian plaza for a street party. The Belles & Bows from Central Florida Vocal Arts stroll the avenue singing carols, and stilt-walking elves work their way up and down the street. The Chamber is also setting up a snowy winter scene at the corner of Morse Boulevard and Park Avenue. Its event list includes s'mores, snow slides, children's choirs and what it calls "a snowy surprise."
Santa's schedule has fixed times. He arrives at 6:30 p.m., courtesy of the Winter Park Fire-Rescue Department, and Santa and Mrs. Claus are available for visits and photos until 8.
The night ends in the park. At 8 p.m., Popcorn Flicks in the Park, presented by the Enzian Theater and the Community Redevelopment Agency, screens It's a Wonderful Life. The Chamber invites people to bring blankets or chairs and pick up dinner from a downtown restaurant for a picnic.
Thursday's crowd settles in one spot, while Friday's moves around. The tree is near the station, the snow is at Morse and Park, the carolers walk the length of the avenue, and the movie brings everyone back to the lawn at the end.
The Morse Stays Open Late on Friday
Friday's events reach past Central Park. The Morse Museum's Holiday Friday Nights offer free admission from 4 to 8 p.m., with live music from 5 to 8, on four Fridays in a row: November 27 and December 4, 11 and 18. The Chamber lists the Museum's Friday night in its own Winter On the Avenue program, so December 4 offers both on the same evening.
The Museum's current exhibition, Revolt in the Parlor: Escaping Victorian Taste, opened October 13. It fills three galleries with more than 250 objects from 1890 to 1959. If you see the Tiffany windows outdoors on Thursday, you can go back for free on Friday to see what the McKeans collected beyond them.
Saturday Morning Moves Onto the Avenue Itself
Saturday morning has no lawn crowd and no evening schedule. It's a parade down the main street. The 74th annual Ye Olde Hometown Christmas Parade, hosted by the Chamber, runs from 9 to 10:30 a.m. on Saturday, December 5.
The route follows Park Avenue. It starts at Cole Avenue, heads south, turns at New England Avenue and ends at Pennsylvania Avenue. The Chamber says more than 80 organizations take part, including marching bands, local police and fire departments, scouting groups, local dignitaries and Santa Claus.
Because of the turn at New England, the last part of the parade leaves the stretch most people picture as "the avenue." If you live south of downtown, the end of the route near Pennsylvania Avenue may be your closest viewing spot.
Saturday Night Brings the Park Back to a Third Host
At 6:30 that evening, Central Park changes hands again. Chabad of Greater Orlando presents Chanukah on the Park, featuring a stunt show by performer Kirill Rebkovets. The menorah lit on Friday was part of the Chamber's program. Saturday night is Chabad's own event, with its own audience, a day after the tree lighting.
Over the three days, the Morse's seated concert holds the north lawn first. Next comes the Chamber's Friday program, which runs from the train station along Park Avenue, followed by its Saturday parade on the street, before Chabad brings the crowd back into the park. Each event works best if you show up at the time and place its host has set.
The Rest of the Season Runs on Separate Calendars
The City of Winter Park's holiday events calendar shows that the weekend sits in the middle of a longer stretch:
- Thanksgiving Weekend at the Morse: Free admission Friday, November 27, 9:30 a.m. to 8 p.m. with live music from 5 to 8; Saturday, November 28, 9:30 a.m. to 4 p.m.; and Sunday, November 29, 1 to 4 p.m. Museum Store Sunday is November 29.
- A Christmas Survival Guide: Performances from November 20 through December 17.
- Christmas Vespers at Rollins College: December 4 through 6 at 6 p.m. Rollins' Department of Music presents carols, readings and performances by the college's choral and instrumental ensembles. On Friday this overlaps with Winter On the Avenue.
- A Classic Christmas at Knowles Memorial Chapel: December 12 and 13 at 1 and 3:30 p.m.
- Christmas Eve at the Morse: Free admission Thursday, December 24, 9:30 a.m. to 4 p.m., with live music from 1 to 4.
New Places to Eat Before the Lawn Fills Up
Both Friday's picnic invitation and Thursday's 4 p.m. setup mean you'll probably want food before you go. Several new spots around downtown have arrived since early fall.
Mecatos Bakery & Cafe soft-opened October 6 at 610 W. Morse Blvd. in the former Coop space, serving Colombian coffee and baked goods. Bungalower reported hours of 7 a.m. to 6 p.m. on weekdays and 8 a.m. to 6 p.m. on weekends. It's on Morse Boulevard, the same street where the Chamber's snow scene meets Park Avenue on Friday.
Fresh Kitchen opens Tuesday, November 17, at 818 S. Orlando Ave. in the former Chicken Guy space. FOX 35 Orlando reported that the Tampa-based build-your-own-bowl chain will hold a 10 a.m. ribbon-cutting with the Winter Park Chamber of Commerce and open its doors at 11 a.m. A Friends & Family preview on November 15 and 16 offers $5 bowls, with proceeds going to the urban agriculture program Fleet Farming. Time slots must be reserved in advance.
UniMart has announced a second konbini for December at 501 N. Orlando Ave., Suite 227, in the Center of Winter Park. Orlando Weekly reported that the new shop will add fresh produce, matcha and soft serve to the usual Japanese grab-and-go foods and gifts.
Kiwi & Fern, the plant and retail shop in the Harmon Collective, took over that location's coffee program on October 17, according to Your Community Paper.
Further out, Orlando Weekly reports that Saikō plans another Winter Park cafe next spring at 1251 Miller Ave. The menu will include matcha, hojicha, coffee, craft mocktails on tap and pastries from Chøkolat.
At Evolve Property Group, we follow Winter Park's calendar the way we follow our owners' properties, with attention to the details that shape daily life here. If you own a rental near downtown and want to know how it fits into a neighborhood with a busy season like this one, ask us for a Free Rental Analysis.
