Best Ways to Celebrate the Holidays in Winter Garden

Winter Garden is a romantic date night destination any time of year. But it's especially charming during the holidays when the city is aglow with twinkling lights and ripe with holiday festivities for celebrating the season. From embarking on a holiday dessert food tour (complete with a golf cart tour of neighborhood lights) to snuggling up in a horse drawn carriage or catching a free movie under the stars, here are a dozen amazing ways to enjoy the holidays in Winter Garden with your love.

A Christmas Story at Garden Theatre

November 24 – December 23, 2018
Garden Theatre
Based on the humorous writings of Jean Shepherd and the motion picture of the same name, you’ll want to make this wonderful, nostalgic bit of Americana part of your family’s holiday celebration.
$30 – $35

A Merry Winter Garden Light Show

December 7, 8, 15, 22, 2018
6 – 9pm
300 W. Plant St.
Spectacular animated light show projected onto the front façade of Winter Garden City Hall.

Holiday Music at Fridays on the Plaza

December 7, 14, 21, 28, 2018
7 – 9pm
Winter Garden Centennial Plaza Gazebo (101 W. Plant St.)
Come enjoy live music every Friday night on the Plaza! The December line up includes talented musicians performing your favorite holiday tunes.


  • December 7- Nicole Equerme w/Sam Trawick (Holiday Music)
  • December 14- Key Harmony (Acapella Holiday Music)
  • December 21- Safia Hudson Trio (Holiday Music)
  • December 28- Paint it Black Quartet (Holiday Music)

Winter Garden Food Tours Christmas Dessert Tours

December 8, 9, 12, 13, 15, 19, 20, 21
6pm and 8pm tours available
Tours begin at Centennial Plaza
See the best Christmas lights in town on a guided golf cart tour while enjoying some Cocoa and sweet treats. No walking required! Tour includes a 1-hour golf cart tour and five tasting stops.

Image credit: Winter Garden Food Tours

A Very Merry Farmers Market

December 8, 15, 22, 2018
9am – 2pm
Winter Garden Downtown Pavilion (104 S. Lakeview Ave.)
Visit Santa, shop for seasonal food and gifts, and enjoy holiday music.

Holiday Carriage Rides

December 8, 15, 22, 2018
5 – 9:30pm
Carriage rides begin at the Winter Garden Downtown Pavilion (104 S. Lakeview Ave.)
$65 for 15 minutes
Reservations required, call 407.656.4111 or visit

Meet Santa at Plant Street Market

December 8, 15, 2018
Times vary
Plant Street Market
Join the festivities on Saturday, December 8, 2018 from 3pm-6pm and Saturday, December 15, 2018 from 12pm-3pm as Santa Claus mix, mingles and spreads holiday cheer for all of Winter Garden to hear!

Old-Fashioned Hayride with Santa

Saturday, December 8, 2018
6 – 9pm, departing every 30 minutes
Winter Garden Downtown Pavilion (104 S. Lakeview Ave.)
FREE, call 407.656.4111 for reservations

Annual Santa Bike Ride

Saturday, December 15, 2018
3 – 8:30pm
Ride begins at Winter Garden Wheel Works
Enjoy a meet and greet with Santa and his elves outside of the shop from 3 – 5:30pm, then decorate your bike for the relaxed 2-mile community bike ride (led by Santa of course!) beginning at 6pm. Drinks and snacks will be provided after the ride.

Image credit: Winter Garden Wheel Works

Holiday Movie Night: Polar Express

Saturday, December 15, 2018
6 – 8:30pm
Winter Garden Downtown Pavilion (104 S. Lakeview Ave.)
Bring a blanket or chair to watch this holiday classic under the stars! The movie will be preceded by a holiday caroling performance from a Dickens-era quartet. Caroling begins at 6pm followed by the movie at 6:30pm.

Holiday Golf Cart Parade

Sunday, December 16, 2018
5:30 – 7pm
Tour begins at Bradford Park
Head to the streets of downtown Winter Garden to watch a parade of golf carts cruising by and decked out in holiday decor. The tour begins in Bradford Park and ends at the north end of Walker Field near the Plant Street Market

Image credit: Winter Garden Golf Cart Parade

Home Alone: Interactive Film & Fun

Sunday, December 16, 2018
Pre-show entertainment begins at 6:30pm, movie at 7:30pm
Garden Theatre
Celebrate the Christmas season with an interactive screening of the classic family comedy, Home Alone! Before the movie begins, enjoy Christmas-themed games, come dressed to impress for the Ugly Christmas Sweater Contest, and participate in “Finish the Christmas Carol” and other trivia games. Miss P. Tart will be your host for the evening. All tickets include a prop bag.

For more details, visit

Florida food and travel photographer and writer Stephanie Patterson

About the Author
Stephanie Patterson is the editor of Orlando Date Night Guide. She’s a talented professional food and travel photographer and writer with a passion for creativity, the beach and great eats. When she’s not taking photos or writing, you can find her exploring the state for her Florida travel blog, Travel Taste Click. Find her online at and