Holiday Market at Downtown 2023 – December 2

Winter Garden Holiday Market Flyer 2023

Holiday Market 2023
Saturday, December 2
1:00 – 4:00 pm
Historic Downtown Winter Garden


Wander freely through the pedestrian-only streets of historic downtown aligned with vendor booths of holiday décor, ornaments, flowers, gingerbread cookies & breads, desserts, chocolates, arts and crafts, jewelry, apparel and accessories, as well as a variety of gift items and more! 

Check items off your gift list, discover items to make your home and holidays festive, indulge in holiday sweets, and enjoy festive entertainment and activities. Plus, with the streets closed, you can enjoy downtown with no worry about cars or traffic. 

Look for the Holiday Market booths and entertainment along West Plant Street from Woodland Avenue to Lakeview Avenue, as well as along South Main Street, and South Lakeview Avenue (stretching from Plant Street to Tremaine Street).

The Holiday Market is a great way to support local businesses while making merry memories! 


Free live holiday entertainment (1:00 - 4:00 pm) will add to the festivities:

Dickens Carolers

Traditionally dressed Dickens Carolers will serenade shoppers throughout the market as they stroll and sing holiday classics a cappella. 

Holiday Caricature Hand Drawings

A caricature artist will hand draw caricatures, with a holiday twist, for attendees. Stop at the Holiday Caricature Booth to have a complimentary custom take-home artwork created to mark this holiday memory. 

Holiday Story Time & Hot Cocoa

Gather the kids for an outdoor story time of holiday classics! Children will love the tales while sipping complimentary hot chocolate.
Story time starts at 1:00 pm, 2:00 pm, and 3:00 pm outside of Writer's Block Bookstore, 32 W. Plant Street. 

Garden Music School Band

The youth band will provide a holiday performance during the Holiday Market, 1:00 - 3:00 pm, at the stage on West Plant Street and North Lakeview Avenue.

Gingerbread Character Meet and Greet

Look for the roaming Gingerbread character to meet and greet -- and pose for holiday photos.


Take pictures at holiday-themed photo stations located throughout downtown. The festive backdrops are perfect for holiday photo cards, social media, and to preserve fun memories in pictures! 


All of historic downtown is decorated like a holiday wonderland with seasonal displays and lighted decorations. The historic small town charm is accentuated by the traditional holiday decorations, reminiscent of a Norman Rockwell painting. Downtown is definitely holiday central for making merry memories and providing the perfect backdrop for breathtaking photos. 


Embrace the holiday charm by grabbing a spice latte, a hot chocolate, a caramel Boba tea, or your favorite beverage. Be sure to get a gingerbread cookie or cake to go along with it. Or, perhaps some peppermint ice cream or holiday chocolates will satisfy your holiday sweet tooth. 


As you leisurely stroll the outdoor market along the festive-adorned streets, holiday music fills the air with a repertoire of familiar holiday tunes playing through the city sound system to sing along. 


Bring your four-legged furry family members too as the outdoor market is dog friendly (leash required) and has lots of great photo ops. You will even find pet holiday accessories, gifts, and treats for sale - including gingerbread flavored! The event is truly a fun outing for the entire family!

GINGERBREAD HOUSE MAKING FAMILY EVENT (hosted by Winter Garden Art Association)

The SOBO Art Gallery, located amidst the Holiday Market, is hosting a Gingerbread House Making Class immediately after the Holiday Market. Not only is it a fun holiday activity, the Gingerbread House serves as a perfect decoration for the holidays. RESERVATION required and spots fill quickly.

SOBO provides step-by-step guidance, one preassembled base, house, and everything you could want to make your masterpiece.

Saturday, December 2, 4:00 – 5:30 pm
$42 per house for 1 Adult and 1 Child
$65 each for additional artists working on the same house
Class fills quickly. Click here to register.

ROAD CLOSURES (December 1 at 10:00 am through December 2 at approximately 11:00 pm)

West Plant Street from Dillard Street to Park Avenue, as well as adjoining side streets, will be CLOSED for the Holiday Market, providing a convenient way to enjoy downtown.

PARKING – Always Free!

Parking is always free downtown, including at the public three-level parking garage (160 S. Boyd St.), 117-space parking lot (37 N. Boyd St.), Sam Williams Little League Complex (415 S. Park Ave.), and a little further up the road at Veterans Memorial Park (420 S. Park Ave.). NO Shuttle Services are available for this event.

Parking along West Plant Street from Dillard Street to Park Avenue, and a portion of the adjoining side streets, will not be available for parking due to the road closures.


To add to the day's celebratory fun, come early for A Very Merry Farmers Market (8 am - 1 pm) and the Winter Garden Christmas Parade (10 am) just before the Holiday Market, and stay after the Holiday Market for the Winter Garden Christmas Golf Cart Parade
(6 pm).

A Very Merry Farmers Market

The festive-decorated market boasts more than 100 vendors and holiday items galore.
8:00 am - 1:00 pm
Downtown Pavilion, 104 S. Lakeview Avenue 

Winter Garden Christmas Parade

Holiday floats and groups from the community parade through historic downtown at the delight of spectators. Look for Santa and Mrs. Claus on the last float! The parade kicks off at 10:00 am from Wells Fargo on Dillard Street and proceeds down West Plant Street through historic downtown. Parade ends at approximately 11:15 am.

Winter Garden Christmas Golf Cart Parade

Elaborately holiday-decorated golf carts parade through historic downtown, looping around West Plant Street. The Parade kicks off at 6:00 pm.

 Shop Local and 120th


WARNING of Fraudulent Online Solicitation: Please note that the City of Winter Garden is in direct contact with outside vendors for this event, and NO collection of payment is required for this event. If you receive correspondence by either a third-party company or the likeness of the City of Winter Garden via email or social media about vending at this event and soliciting payment, it may be a  fraudulent solicitation and do NOT engage in providing information or any form of payment. If you have any questions or concerns, contact Betsy Sorg at

 Please Note: The use of drones at City events is prohibited.