Calendar and Family Calendar



An Old Fashioned Christmas

”An Old Fashioned Christmas” will be performed Dec. 9-12 at Breakthrough Theatre of Winter Park, located at 419A W. Fairbanks Ave.


Christmas in the Park

Take in the holiday season at the 38th annual Christmas in the Park from 6:15 to 8 p.m. on Thursday, Dec. 1 in Central Park.


Holiday Pops concert

Celebrate the spirit of the holidays as the Orlando Philharmonic Orchestra presents its annual Holiday Pops concert at Winter Park’s Central Park on Nov. 27.


Winter in the Park

Beginning Friday, Nov. 18 through Sunday, Jan. 8, the city of Winter Park will host Winter in the Park, the city’s annual holiday ice skating rink at Central Park West Meadow on the corner of New York Avenue and Morse Boulevard.

Tease photo

Great Day in the Country is back!

Craft festival

Great Day in the Country Arts and Crafts Festival is back for its 43rd year on Saturday, Nov. 12!


Veterans Day Celebration

This Veterans Day, Winter Park will host its sixth annual Veterans Day Celebration to honor heroes of the city. The event will be at the Winter Park Community Center Ruby Ball Amphitheatre, 721 W. New England Ave.


Chalk the Walk

Winter Park’s Parks and Recreation Department is pleased to present “Chalk the Walk” in Central Park on Saturday, Nov. 5 from 8 a.m. to 4 p.m. Artists will decorate the sidewalks of Central Park with art.

Senior Calendar

Festival of Trees

Tickets are now on sale for one of Central Florida's favorite holiday traditions: Festival of Trees, which runs Nov. 12 to 20 at the Orlando Museum of Art, located at 2416 N. Mills Ave.

Tease photo

Goldenrod Parade and Festival arrives!

Parade, pancakes, fun

Come out to the Goldenrod Festival and Parade on Saturday, Oct. 29, at the Goldenrod Station!


Halloween Pet Costume Contest

On Sunday, Oct. 30, it's time for the 17th annual Pet Costume Contest hosted by The Doggie Door in Winter Park's Central Park.

Tease photo

Oktoberfest returns to Winter Park

German festival Oct. 26

Like beer, music and a festive atmosphere? Winter Park is about to give it to you German style.


Winter Park’s Oktoberfest

Come out to Winter Park’s Oktoberfest, featuring authentic German beer, food, music, a yodeling competition, a stein-holding competition and more!


'Young Frankenstein' at Theatre UCF

Just in time for the Halloween season, Theatre UCF comes alive with “The New Mel Brooks Musical Young Frankenstein,” running Oct. 20 to 30 on the UCF Main Stage.


Winter Park Wine & Dine

The 2016 Winter Park Wine & Dine event will be held on Wednesday, Oct. 12, from 6 to 9 p.m. at the Winter Park Farmers Market.


Winter Park Autumn Art Festival

Get your art fix at the 43rd annual Winter Park Autumn Art Festival in Winter Park’s Central Park on Oct. 8 and 9.