Winter Park Chamber Sets Holiday Event Calendar

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Stormy weather may dampen the season but not the spirit. And the local holiday calendar is already filling with festive events ranging from a shopping stroll to a special anniversary.

The Winter Park Chamber of Commerce will present a series of celebrations from Nov. 17 to Dec. 3. Events are as follows:

Sip, Shop & Stroll: 5-8 p.m. Thursday, Nov. 17, on Park Avenue; Presenting Sponsor: Fannie Hillman + Associates

The event began five years ago with the intent of showcasing the Park Avenue business district. This year’s stroll will include 13 participating businesses, and guests can enjoy wine and light hors d’oeuvres along the way. Admission is $25 per person, tickets are available in person or at Guests must check-in at Fannie Hillman + Associates, 122 S. Park Ave. “It’s a beautiful way to enjoy your wine while making your way down the avenue,” said Betsy Gardner Eckbert, President and CEO of the Winter Park Chamber.

• Winter On The Avenue: 5-9 p.m. Friday, Dec. 2, at Central Park; Presenting Sponsor: Massey Services, Inc.

Enjoy the annual tree-lighting and a menorah-lighting ceremony, strolling carolers, and Popcorn Flicks in the Park presented by the Enzian Theater. There will also be s’mores, an appearance by the Bubble Bus, and a visit from Santa Claus. Park Avenue will be closed, beginning at 2 p.m., as the downtown area is transformed into a pedestrian plaza. New England Avenue will remain open to thru traffic.

• Leadership Winter Park Pancake Breakfast: 7-10 a.m. Saturday, Dec. 3, by the Central Park Stage; Presenting Sponsors: AdventHealth, Florida Blue and Valley Bank

Pancakes, sausage, and a toppings bar will be presented by the Glass Knife. All are included with a choice of beverage for $7 per person. Tickets are available on site or in advance at Proceeds benefit adult and youth leadership development programs, and school supply donations. Click here for ticket purchases.

• Ye Olde Hometown Christmas Parade: 9-10:30 a.m Saturday, Dec. 3, along Park Avenue and New England Avenue; Presenting Sponsor: Balfour Beatty

Celebrate 70 years of Ye Olde Hometown Christmas Parade with more than 80 entries including the Winter Park, Bishop Moore, and Edgewater High School marching bands. The Winter Park fire and police departments, and scout troops will be represented. And it all culminates with a visit from Santa Claus. A special float bedecked in gold will celebrate the Winter Park Chamber’s 100th Anniversary in 2023.

For more more information on the holiday calendar and other Winter Park Chamber events, please visit

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