Downtown is Merry & Bright

November 26, 2024

When you combine the small-town charm of historic downtown Winter Garden with its festive decorations, you get the quaintest holiday wonderland that’s fitting for a Hallmark movie. Besides the festive ambiance, downtown events throughout December are sure to create merry experiences to make the holiday season extra special.

Light Up Winter Garden

The holiday season kicks off with the 37^th annual Light Up Winter Garden on Friday, December 6, 6 – 9 p.m. In addition to downtown aglow, there are children snow play areas, live music, strolling holiday entertainment, Santa visit area, and so much more!

Winter Garden Christmas Parade

The Winter Garden Christmas Parade (December 7 at 10 a.m.) is a long-standing tradition that delights spectators and exudes holiday cheer! Bring a lawn chair or blanket and head to your favorite viewing spot.

Holiday Night Market

Market stalls of holiday goods, gifts, and treats line the Downtown Pavilion area for the first Holiday Night Market on December 7, 4 – 8 p.m. Cheerful entertainment including Dickens Carolers, holiday story time, local school chorus groups, and even a visit from Santa himself will add to the festive market atmosphere! In fact, the weather is predicting snow flurries! Be sure to stop by the City of Winter Garden booth for a free commemorative Holiday Night Market reusable tote bag (while supplies last).

Winter Garden Golf Cart Parade

The Winter Garden Christmas Golf Cart Parade is a yearly holiday occurrence that never disappoints. Whether you are a participant or bystander, everyone will enjoy the procession of joyous decorated golf carts on Saturday, December 7, at 6 p.m.

Holiday Flix at the Garden – New!

Enjoy a cozy, nostalgic holiday movie at the historic Garden Theatre for the great price of $5 with Holiday Flix at the Garden. The classic It’s a Wonderful Life will be shown on December 10 at 4 p.m. and on December 11 at 7 p.m. Catch the holiday favorite Elf on December 17 at 4 p.m. and December 18 at 7 p.m. Hosted by the City of Winter Garden, get your tickets now!

Holiday Opera at the Garden – New!

Holiday Opera at the Garden is a magical and heartwarming concert featuring world-class soprano Samar Salamé Hawat. The festive performance is a beautiful blend of classical repertoire with iconic Christmas carols in the magnificent setting of the historic Garden Theatre. Hosted by the City of Winter Garden, the event will be held on Saturdays, December 14 and 21, 7 – 8 p.m. Get your tickets now!

A Merry Winter Garden Light Show

A warm and joyous tradition for many locals. Come enjoy A Merry Winter Garden Light Show, a spectacular animated holiday-themed light show synchronized to music projected onto the front façade of Winter Garden City Hall. The display runs in a continuous loop from 6 – 9 p.m. on December 6-8, 13-15, and 20-22. On those same nights, be on the lookout for holiday street performers throughout downtown, providing festive music and fun antics.

Main Street Holiday Stroll – New!

New this year, the Main Street Holiday Stroll is a festive addition to downtown with a picturesque, season-long display of Christmas trees, glittering decorations, twinkling lights, and store fronts shining bright. Located on South Main Street between West Plant Street and West Joiner Street, the walk-through display is open every day from December 6 through January 5.

Horse Drawn Holiday Carriage Tours

Brought to you by SOUL Haven Ranch, aboard your chariot and take a magical 20-minute Horse Drawn Holiday Carriage Tour through festive downtown Winter Garden. Available from 5:30 – 9:30 p.m. on December 9-12, 16-19, 23, and 24. Limited spots so book your tour now at SOUL Haven Ranch. Reservations recommended / fee required.

Holiday Fridays on the Plaza

Your weekly Fridays on the Plaza will turn merry and bright during the month of December. Enjoy live holiday music on Fridays, 7 – 9 p.m. at the Centennial Plaza in the center of downtown. Grab a nearby swing, bring a chair, or hum along to the holiday tunes as you stroll by.

A Very Merry Farmers Market

Santa Claus is making a special stop at the Winter Garden Farmers Market on Saturdays, December 14 and 21, 9 a.m. – 12 p.m. It is a great opportunity to visit with Santa and pose for photos. Create your wish list at the kids’ craft tent and drop it in the special mailbox that delivers straight to the North Pole.

Every Saturday in December is merry at the market (open 8 a.m. – 1 p.m.)  with festive gifts, seasonal décor, sweet treats, fresh produce, artisan foods, and more! Downtown Pavilion, 104 S. Lakeview Ave.

Holiday Shopping

Look no further than downtown to find the perfect gift! Local owned shops have one-of-a-kind gifts and personalized customer service in a stress-free atmosphere, making shopping a pleasurable experience. From apparel, accessories, jewelry, and sporting goods to home décor, gourmet seasonings, bakeries, chocolate shops, and more, downtown is one-stop shopping.

Holiday Dinning

The variety of eateries downtown (casual, upscale, or just a sweet treat) make it easy to find the right spot to celebrate the season with family and friends. Outdoor dining provides a close-up view of the holiday decorations adding to the occasion. Cheers!