10 Romantic Holiday Events in Winter Garden to Celebrate the Season

SPONSORED – With its quaint brick-lined streets, local eateries and boutiques, and paved pathways, Winter Garden is one of our favorite locales for date night. This year is looking especially merry with hundreds of twinkling lights and a large Christmas tree adorning the city plus a calendar full of festive events to enjoy with your favorite plus one. From horse-drawn carriage rides to holiday performances, live out your own holiday romance with this list of a dozen date night-approved holiday events in Winter Garden.

A Christmas Carol – A Ghost Story of Christmas at Garden Theatre

Through December 22, 2019
Garden Theatre
This spirited version of A Christmas Carol puts the ghostly qualities of Charles Dickens’ classic tale on center stage. A swirling chorus of ghosts weave through this uplifting holiday story of redemption, magic, and hope as the greedy Scrooge learns the error of his ways.
$25 – $37

A Christmas Carol at Garden Theatre
Image credit: Garden Theatre (photo by Patrick R. Murphy)

Holiday Boutique Crawl

December 5, 5-8pm
Historic Downtown Winter Garden
Join downtown Winter Garden retailers specializing in women’s apparel and accessories for a fabulous evening of shopping, sips and snacks.
FREE admission

Holiday Events in Winter Garden - Holiday Boutique Crawl 2019

A Very Merry Farmers Market

December 7, 14 and 21, 9am-2pm
Winter Garden Downtown Pavilion (104 S. Lakeview Ave.)
Visit Santa, partake in a wreath-making workshop (fee), shop for seasonal food and unique gifts, see seasonal food demonstrations and podcasts, and join outdoor yoga classes. Santa will be at the market December 14 & 21.
FREE Admission

Holiday Carriage Tours through Downtown Winter Garden

December 7, 13, 14, 20 and 21, 5:30-9:30pm
Starting at the Winter Garden Downtown Pavilion
104 S. Lakeview Ave.
The weather — as well as the quaint charm and festive scenery — are lovely for a horse drawn carriage tour through Historic Downtown Winter Garden! Holiday Carriage Tours last 15 minutes and can accommodate up to 4 adults or 2 adults and 3 children.
Reservations required; online or call 407.509.1981

Image credit: SOUL Haven Ranch

A Merry Winter Garden Light Show

December 7, 13, 14, 15, 20, and 21, 6-9pm
300 W. Plant St.
Feast your eyes on a spectacular animated holiday light show synchronized to music projected onto the front façade of Winter Garden City Hall.

Holiday Music at Fridays on the Plaza

December 13, 20, 27, 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 13 – Key Harmony
  • December 20 – Roots & Rosin/Nicole Equerme/Abigail Collins
  • December 27- Paint it Black Quartet

Holiday Golf Cart Parade

December 15, Parade Viewing begins at 5:45pm
Plant St. from Central Ave. to Main St.
Golf carts adorned with impressive holiday decorations will parade through downtown Winter Garden to amaze viewers.

Holiday golf cart parade in Winter Garden, FL
Image credit: Winter Garden Christmas Golf Cart Parade

Garden Theatre Interactive Movies: Home Alone 2 – Lost in New York

December 15, 7:30pm
Garden Theatre
The Wet Bandits are back! Can Kevin stop them from ruining Christmas in The Big Apple? Be a part of the movie in this fun interactive movie series.

Dickens Carolers on the Plaza

December 21, 6:30–8:30pm
Centennial Plaza Gazebo (101 W. Plant St.)
Listen to a quartet of traditional Dickens-era carolers performing a repertoire of holiday favorites.

Holiday events in Winter Garden - Dickens Carolers

Annual Santa Bike Ride

December 21, 3-8pm
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.

Feature image Courtesy of the City of Winter Garden

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