Know Before You Go: Holiday Events in Winter Park

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It may seem early for holiday event planning, but the parties are about to begin. Local businesses and organizations are gearing up for celebrations that will be framed by all-new downtown décor, presented by the Park Avenue District.

Fresh, festive features will be installed by Thursday, Nov. 14, and include:

  • A lighted silhouette of Park Avenue buildings.
  • 800 globe lights in the trees along the avenue.
  • New wreaths made of Temple oranges, white magnolias, berries, and pinecones.
  • A new Christmas tree in Central Park.
  • Scent diffusers filing the air with aromatic holiday accents.
  • A walk-through “cathedral of lights” feature.

The decorations along the avenue will be illuminated during a special evening event on the 14th, and Park Avenue District is asking shops to stay open late as “elves” turn on the lights. The evening will also feature the district’s special patrons party, Light Up Park, to thank those who helped the 2024 holiday effort and invite those who want to pitch in for next year’s plans. The party will run from 6-9 p.m. at Winter Park Country Club and tickets are available on the event page.

“The evening of November 29th will be another date for the calendar,” said Park Avenue District Executive Director Carina Sexton, “We will open a new holiday carousel by City Hall the night before Shop Small Saturday begins on the 30th.”

Winter Park Playhouse will also celebrate the season with the Southeastern regional premier of Wreck the Halls, November 15 – December 21. The musical comedy is presented in a series of comic and poignant vignettes with four actors playing 46 characters in a celebration of everything that we love and can’t stand about Christmas. Tickets and event information are available on the playhouse website.

Two annual events that will not be on this year’s calendar are the Winter Park Holiday Boat Parade and the Pop-Tarts Bowl Parade of Bands, formerly the Cheez-It Bowl Parade of Bands.

“We appreciate all those boaters who normally participate and the spectators who attend, but due to several issues, we must postpone until next year,” Rotary Club member Johnny Hurlburt told the32789. Plans are to bring back the boat parade next year on December 13, and the Rotary Club is presenting a big band concert in Central Park on Saturday, Dec. 14 (information posted in the holiday schedule).

Jill Mickle, Florida Citrus Sports director of events, said this year’s Pop-Tarts Bowl Parade of Bands had to be canceled due to a new kickoff time. “The game usually starts at around 5 p.m. but that was moved up to 3:30 p.m.,” she told the32789. “We just won’t have time to bring in the band, set up and have the parade, and make it to the stadium by game-time.”

The Winter Park holiday schedule features plenty of community spirit. Events are coordinated by several organizations such as Winter Park Chamber of Commerce, Orlando Philharmonic Orchestra, and Chabad of Greater Orlando. See the listings for dates, times, and links to more information. And check the City or Winter Park event calendar for additional daily listings.

46th Annual Christmas in the Park: Thursday, Dec. 5, 6:15-8:30 p.m. in Central Park

Image shows ensemble wearing all black and holding black books to read music from during a concert.
Photo courtesy of: Bach Festival Society

The Charles Hosmer Morse Museum of American Art continues its holiday tradition as lighted turn-of-the-century Tiffany windows highlight Central Park Main Stage performances by Bach Festival Society Choir, Youth Choir, and Brass Ensemble. Guest can begin setting arranging lawn chairs and blankets at 4p.m., after the windows are installed. For more information, see the event page on the Morse Museum website.

The Morse Museum also hosts Holiday Friday Nights in November and Deceber. Guests can enjoy free admission from 4-8 p.m., and live music beginning at 5 p.m.

• Winter on the Avenue: Friday, Dec. 6, 5-9 p.m. on Park Avenue

Image courtesy of: Park Avenue District

The Winter Park Chamber of Commerce presents this free annual event in cooperation with the City of Winter Park. Guests can witness the official lighting of the Winter Park Christmas tree and a menorah-lighting ceremony, enjoy strolling carolers from Central Florida Vocal Arts, and a visit from Santa. The festivities will be framed by all-new decorations by the Park Avenue District. For additional information, log onto the event page.

72nd Annual Winter Park Christmas Parade: Saturday, Dec. 7, 9-10:30 a.m. on Park Avenue

Photo by: Jim Carchidi

Hosted by the Winter Park Chamber of Commerce, the parade is the oldest continuous holiday parade in Central Florida and includes more than 80 organizations participating with marching bands, floats, and Santa Claus himself.

Before the parade, Winter Park Chamber will present the 24th Annual Leadership Winter Park Pancake Breakfast from 7-10:30 a.m. in Central Park. Pancakes, sausage, and a toppings bar are included with a choice of beverage for $7 per person. Tickets are available on site or in advance at winterpark.org. Proceeds benefit adult and youth leadership development programs, and school supply donations. Click here for more information and tickets.

• Holiday Pops Concert: Sunday, Dec. 8, 6 p.m. at Central Park Main Stage

Photo courtesy of: Orlando Philharmonic

Orlando Philharmonic Orchestra will perform a program of holiday favorites at a free concert, presented by the Charlotte Julia Hollander Trust. Guests are welcome to bring blankets and pack a picnic. Check the event page for more information.

Wreaths Across America: Saturday, Dec. 14, beginning at noon at Palm Cemetery, 1005 N New York Ave., and at Pineywood Cemetery, 1900 S Lakemont Ave.

Photo courtesy of: City of Winter Park

Wreaths Across America will honor the service and sacrifice of America’s veterans by laying remembrance wreaths on the graves of the fallen. The public can participate by volunteering to assist in person or by sponsoring a wreath. Click here to access volunteer and sponsorship information for Palm Cemetery, and here for Pineywood Cemetery.

Merry TubaChristmas: Saturday, Dec. 14, beginning at 1 p.m. at Central Park Main Stage

Photo by: Jim Carchidi

Baritone players of all ages will perform a free concert of holiday favorites in the impressive register of tubas, euphoniums, and sousaphones. Musician registration begins at 9 a.m. and the fee per musician is $10. Rehearsal is from 10-11:30 a.m. Performers must bring a folding chair and music stand. For more information, call 407-599-3463.

Orlando Big Band Christmas Concert: Saturday, Dec. 14, beginning at 7:00 p.m. at Central Park Main Stage

Photo courtesy of: Orlando Big Band

Enjoy a free concert in Central Park by The Great American Big Band and the Rotary Club of Winter Park. The 1940’s orchestra will present a showcase of holiday music with a vintage flair. For more information, log onto GreatAmericanBigBand.com.

• Chanukah on the Park: Wednesday, Dec. 25, beginning at 5 p.m. in Central Park

Photo courtesy of: City of Winter Park

Chabad of Greater Orlando will present an evening of celebration with entertainment, kids’ activities, food, and a grand menorah lighting. For more information, access chabadorlando.org.

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