Christmas Vespers at Rollins College
Rollins College

The Sunshine State is full of holiday cheer.

If you’re looking for a Southern Christmas celebration packed with holiday cheer, you should plan a trip to Winter Park, Florida, this December.

Just a stone’s throw northeast of Orlando, the Winter Park festivities begin on December 1st, when the town’s Winter on the Avenue street party kicks off the holiday season. Everyone’s invited to Park Avenue, the town’s central thoroughfare, which lights up the night with festive decorations, family-friendly entertainment, and even a visit from Santa Claus. Park Avenue shops are open late for browsing, and there’s also live music with plenty of Christmas classics to sing along to.

Winter on the Avenue is filled with countless fun events for families, and we think you’ll want to savor them all while soaking up the town’s abundance of Christmas cheer. There’s a tree lighting ceremony, performances from children’s choirs, and, of course, photo opportunities with Santa and Mrs. Claus. You can bundle up the little ones (or, depending on the weather, bring a light jacket—it is Florida, after all) for twilit outdoor screenings of How the Grinch Stole Christmas and The Santa Clause.

It may be a mild-winter sort of town, but when the holidays arrive, Winter Park lives up to its name. Be sure to bring your sense of adventure and brave the ice for a spin around the Winter in the Park Ice Skating Rink, which is open this season from November 18th through January 7th. When the community spirit and holiday festivities abound, you’ll feel like you’ve been transported to the North Pole.

On Thursday, December 4th, Winter Park's Central Park will host another beloved Christmas tradition. An outdoor concert accompanies the 36th annual Christmas in the Park event, during which The Morse Museum of American Art lights a glowing collection of rare Tiffany leaded-glass chapel windows in Central Park at dusk.

Rollins College is the home of yet another special Winter Park Christmas event. For 80 years, the institution's candlelit Christmas Vespers program has brought visitors into the college's Knowles Memorial Chapel for evenings of music, carols, and scripture readings shared by members of the Rollins College community. This year's Christmas Vespers will be held on the evenings of December 8th, 9th, and 10th.

These three unforgettable Winter Park events—Christmas in the Park, Rollins College's Christmas Vespers, and the Winter on the Avenue extravaganza—will usher you into the holiday spirit in no time at all.

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You don’t want to miss the festivities in this Central Florida winter wonderland. If you’re visiting Disney World this holiday season, Winter Park's nearby small-town Christmas celebration is well worth a visit.