City of Winter Park Announces Annual Holiday Events Lineup

Holiday Pops in Central Park with your Orlando Philharmonic Orchestra: Sunday, December 5

The City of Winter Park is preparing to welcome a flurry of cheerful events this holiday season. Don your holiday apparel and gather with loved ones to experience these annual Winter Park holiday traditions. Access to see a full lineup of all the city’s upcoming holiday festivities.

On Thursday, November 18, the city will start sparkling with light as the Hometown Holidays season begins. Along Park, West New England and Orange avenues as well as Morse Boulevard, the community will see strings and globes of lights, beautiful poinsettia trees, hanging baskets, life-size holiday greeting cards, elegant street banners, and more festive décor. Hometown Holidays will also whimsically surround guests and passersby in Central Park, Martin Luther King, Jr. Park and Shady Park. Merchants throughout downtown Winter Park area will be participating in the holiday season with their Hometown Holiday Window Showcase to complement the holiday theme.

On Thursday, November 18, from 5 to 8 p.m., the Winter Park Chamber of Commerce is hosting Sip, Shop & Stroll. Experience the charm of Park Avenue on this unique Winter Park wine walk. Spend the evening discovering new merchants, checking out the latest fashions, shopping for holiday gifts and tasting seasonal menus. The City of Winter Park will be illuminating their Hometown Holidays lights this evening, making for an especially festive evening stroll. Check-in will be at Fannie Hillman + Associates, located at 122 S. Park Ave. To purchase tickets or get more information, please access

The Park Avenue District is hosting a Park Avenue Holiday Market on Friday, November 19, from 10 a.m. to 5 p.m., in Central Park West Meadow. Enjoy festive music as you stroll through the market, get all your holiday shopping done in one place and check everyone off your list. Stay on your best behavior, as Santa Claus will be making an appearance from 11 a.m. to 4 p.m. Reservations are recommended for Santa. For more information, please access

Chabad of Greater Orlando will present Chanukah on the Park Sunday, November 28, from 5 to 7 p.m., in Central Park. The event will include an art acrobat show, live music, dancers, kids’ activities, jugglers, food and grand menorah lighting. For more information, please access

The City of Winter Park and The Charles Hosmer Morse Museum of American Art continue a holiday tradition with the 43rd Annual Christmas in the Park on Thursday, December 2. The two-hour program begins at 6:15 p.m. in Central Park, creating the beautiful backdrop for the lighting of eight turn-of-the-century Tiffany windows as the Bach Festival Choir performs in concert on the main stage. For this year’s program, there will be pods in the park for attendees to use on a first-come, first-served basis to reduce crowding. For more information about the event, please access

On Friday, December 3, from 5 to 9 p.m., the festivities continue as the Winter Park Chamber of Commerce and the City of Winter Park host Winter on the Avenue. This holiday street party will feature an array of activities including the Annual Tree Lighting Ceremony presenting the city’s holiday tree in Central Park, Santa Claus, Popcorn Flicks in the Park, live music, snow slides from the Parks & Recreation Family Fun Program, s’mores from the Winter Park Fire-Rescue Department, and so much more. For more information, please call 407-644-8281 or access

Presented by Winter Park Community Redevelopment Agency, sponsored by AdventHealth and produced by Enzian Theater, Popcorn Flicks in the Park, featuring Frosty’s Winter Wonderland and The Santa Clause, will take place in Central Park, Friday, December 3, at 7 p.m. Bring a small group of family and friends, and don’t forget to pack a blanket, picnic or snacks. For more information, please call 407-599-3501.

Before and during the Christmas Parade Saturday, December 4, Leadership Winter Park will host the 22nd Annual Leadership Winter Park Pancake Breakfast, at the Central Park main stage from 7 to 10 a.m. Enjoy pancakes, sausage and beverages for just $6 per person. Proceeds benefit the Winter Park Improvement Foundation in its efforts to develop adult and youth leaders through Leadership Winter Park programs. For more information and to purchase tickets, please access

On Saturday, December 4, Park Avenue comes to life at 9 a.m., with the 69 th Annual Winter Park “Ye Olde Hometown” Christmas Parade, hosted by the Winter Park Chamber of Commerce. This family-friendly occasion showcases holiday-themed floats, Santa Claus, and well-known local figures as they make their way down the avenue on an adjusted route. The parade will travel down Park Avenue, turn west on to New England Avenue, and end at the Winter Park Community Center. For more information, please call 407-644-8281.

A special Holiday Pops concert, performed by the Orlando Philharmonic Orchestra, will take place Sunday, December 5, at 5 p.m., in beautiful Central Park. Bring your blanket and a picnic for a concert program of holiday favorites that will be sure to put everyone in the spirit of the season. This free concert is made possible by the Charlotte Julia Hollander Trust. For more information, please call 407-599-3501.

The holiday festivities move from our city streets to a beautiful city lake as the Winter Park Holiday Boat Parade, sponsored by the Winter Park Rotary Club, sets sail on Saturday, December 11, at 6 p.m. Family and friends can gather in their backyards on Lake Virginia or at Dinky Dock Park to see the impressive boat and dock holiday decorations created by residents and local business sponsors. To register a boat in the parade, please access For more information, please call 407-256-6369.

The Charles Hosmer Morse Museum of American Art will offer free admission for four Fridays in December, Friday, December 3, 10, 17 and 31, from 4 to 8 p.m., featuring live music from 5 to 8 p.m. In addition, the museum is also offering free admission on Friday, December 24, for its Christmas Eve Celebration featuring live music from 1 to 4 p.m. To make an appointment please access or for more information, please call 407-645-5311.

To wrap up the holiday season with a bright red bow on top, the City of Winter Park will proudly host the Annual CHEEZ-IT® Bowl Parade of Bands Wednesday, December 29, at 11 a.m. as a prelude to the CHEEZ-IT® Bowl game on Wednesday evening at 5:45 p.m. at Camping World® Stadium. School bands will march through downtown Winter Park and perform a “Bandastic Game Day Preview” in Central Park. For more information, please access

If you’re visiting Winter Park this holiday season and you’re wondering where to park, please access the city’s parking page to plan ahead. Many of the city’s holiday events will require road closures, keep up with these notices by accessing the Closures & Construction page.

Don’t forget, Sunrail will drop you off at the Winter Park Train Station right in the middle of Central Park, making it the perfect mode of transportation to come shop the Avenue or to attend our weekday holiday events. To check the train schedule or purchase a ticket, please access