Shop Small Business Saturday Celebration

November 30

10:00 am – 7:00 pm

Day-long event of Special Sales, Raffle Drawings, Free Live Music to celebrate and support the small, independently-owned business of Winter Garden. Live Music & Raffle at Centennial Plaza Gazebo, 101 W. Plant St.:

Teddy Henderson, 11:00 am – 2:30 pm

Mud Rooster, 3:30 pm – 7:00 pm

Raffle Drawing: 5:00 pm

Downtown Winter Garden

Click here for more info 

Holiday Market at Winter Garden Farmers Market

November 30

9:00 am – 2:00 pm

Shop for holiday/gift-related hand-crafted ítems at special guest vendors.

Winter Garden Downtown Pavilion

104 S. Lakeview Ave.

Click here for more info 

Holiday Boutique Crawl

December 5

5:00 pm – 8:00 pm

Join downtown Winter Garden retailers specializing in women apparel and accessories for a fabulous evening of shopping, sips, and snacks.

Downtown Winter Garden

Join the fun here 

A Merry Winter Garden Light Show

December 7, 13, 14, 15, 20, 21

6:00 pm – 9:00 pm

Spectacular animated holiday light show synchronized to music projected onto the front façade of Winter Garden City Hall.

300 W. Plant St.


Holiday Carriage Tours through Downtown Winter Garden

December 7, 13, 14, 20, 21

5:30 pm – 9:30 pm

Starting at the Winter Garden Downtown Pavilion

104 S. Lakeview Ave.

Cost: $65.00

Reservations required, book here

A Very Merry Farmers Market

December 7, 14, 21

9:00 am – 2:00 pm

Visit Santa, wreath-making workshop (fee), shop for seasonal food and unique gifts, seasonal food demonstrations and podcasts, yoga classes.

Winter Garden Downtown Pavilion

104 S. Lakeview Ave.


Click here for more info 

Holiday Music at Friday’s on the Plaza

December 13, 20, 27

7:00 pm – 9:00 pm

Line up of talented musicians performing favorite holiday tunes:

December 13 - Key Harmony

December 20 – Roots & Rosin/Nicole Equerme/Abigail Collins

December 27- Paint it Black Quartet

Centennial Plaza Gazebo, Downtown Winter Garden

101 W. Plant St.


Holiday Golf Cart Parade

December 15

Staging of participants: 4:00 pm, Bradford Park, 220 W. Division St.

Parade Viewing: begins 5:45 pm along Plant St. from Central Ave. to Main St.

Golf carts adorned with impressive holiday decorations will parade through downtown Winter Garden to amaze viewers.

Click here for more info 

Dickens Carolers on the Plaza

December 21

6:30 pm – 8:30 pm

Quartet of traditional Dickens-era carolers performing a repertoire of holiday favorites.

Centennial Plaza Gazebo

101 W. Plant St.


Visit Santa at the Gingerbread House

Santa Claus is coming to town! Visit Santa in downtown Winter Garden on Saturdays, December 14 & 21, 10 am-1 pm; and on Sunday, December 15, 2-5 pm at the Gingerbread House. Pictures welcome! Free! Santa’s Gingerbread House located at 160 S. Boyd St., Winter Garden.

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