City of Winter Garden, FL

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A charming little city with a juicy past

Special Events

City of Winter Garden
300 West Plant Street
Winter Garden, FL 34787

Tis The Season 2016

Winter Garden will be transformed into a Winter Wonderland – filled with all the festive trimmings!

Take a ride on Santa's sleigh or go for a romantic carriage ride through historic downtown. Enjoy live holiday music, caroling or see Charlie Brown and his friends come to life for A Charlie Brown Christmas! Watch a holiday movie at the downtown pavilion and don't miss the second-annual Merry Winter Garden Light Show at City Hall! Every Saturday in December come out for a Very Merry Farmers Market. This year enjoy the new holiday-themed photo vignettes found in a variety of places in downtown Winter Garden!

Click here for a flyer!

Merry Winter Garden Light Show

City Hall comes alive!

Event Time: 6:00pm to 9:00pm
Event Location: In front of City Hall


Select nights:

December 9, 10, 16, 17, and 23



The Winter Garden Fire Rescue Department will be escorting Santa Claus on his annual visit to neighborhoods in Winter Garden! This moving parade takes place between 5:45 PM and 9:00 PM each night as Santa, along with his firefighter, police, and city helpers spread holiday music, treats, and good cheer along the way. An alternate date is scheduled for December 19th if weather interrupts one of Santa’s visits. Check for Santa’s route any time after December 1st.

Holiday Golf Cart Drive-in

Sponsored by the Garden Theatre

Event Date: Saturday, December 17th, 2016
Event Time: 6:30PM - 9:00PM
Event Location: Downtown Pavillion

Drive your golf cart or bring a chair and enjoy a classic holiday movie!

6:30 - Mickey's Christmas Carol

7:00 - Dr. Seuss' How the Grinch Stole Christmas

Martin Luther King, Jr. Celebration

An event honoring Dr. Martin Luther King, Jr.

Event Date: Saturday, January 14th, 2017
Event Time: 1 - 4 pm
Event Location: Orlando Magic Gym, 309 S. West Crown Point Road

Come celebrate and honor this great leader of the civil rights movement. Enjoy entertainment, speakers, vendors, kids’ activities and much more! A community march will travel from East Bay Street to the Orlando Magic Gym. To participate in the march, please meet at 118 E. Bay Street at 12:30pm. For a vendor application form, please click here.

Little Cupids Carnival

Event Date: Tuesday, February 14th, 2017
Event Time: 10 am - 12 pm
Event Location: Jessie Brock Community Center, 310 North Dillard Street

A special sweetheart filled morning for children ages 3 to 5! Join us for arts & crafts, fun games, face painting and so much more! Bring a friend or a group. Group headcounts are required in advance.

6th Annual Winter Garden Blues & BBQ

Event Date: Saturday, February 18th, 2017
Event Time: 4 - 10 pm
Event Location: Downtown Pavilion, 104 Lakeview Avenue

FREE Admission • BBQ available for purchase This festival pairs the hottest Blues and Roots musicians with award winning local BBQ connoisseurs, for an afternoon celebration of true Southern Soul. An exciting annual event that is not to be missed! For a vendor application form, please click here. *All profits benefit the American Cancer Society

Ongoing Events:

Winter Garden Farmers Market

Event Time: Saturdays 9am - 2pm
Event Location: City Pavilion, Tremaine Street

The Winter Garden Farmers Market is your hometown market open every Saturday from 9:00am to 2pm in beautiful Historic Winter Garden. 

The Market has quickly grown into a community staple and offers a large selection of vendors from locally grown produce and baked goods, to homemade soaps and fresh flowers, and even live entertainment each week! 

Bring the whole family (even your four-legged friends) and experience what makes the Winter Garden Farmers Market so special. 

Enjoy LIVE MUSIC every Saturday from 10:00am to 2:00pm