Holiday Market at Downtown Winter Garden

Holiday Market – plus Free Merry Entertainment & Activities
December 2, 2023
1:00 pm – 4:00 pm
Historic Downtown Winter Garden
HOLIDAY MARKET – OUTDOOR & PEDESTRIAN ONLY
Join us for an outdoor holiday market 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! Look for the Holiday Market booths 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!
MERRY ENTERTAINMENT & ACTIVITIES – All FREE, 1:00 – 4:00 pm:
DICKENS CAROLERS
Traditionally dressed Dickens Carolers will serenade shoppers throughout the market as they stroll and sing holiday classics a cappella.
HOLIDAY CARICATURE TAKE-HOME 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
Gather the kids for an outdoor story time of holiday classics! Children will love the tales while sipping complimentary hot cocoa samples. (Holiday pajamas welcome!) Story time starts at 1:00 pm, 2:00 pm, and 3:00 pm outside of Writer’s Block Bookstore, 32 W. Plant Street.
MORE REASONS TO ENJOY THE HOLIDAY MARKET:
HOLIDAY WONDERLAND
Downtown has all the sights and sounds of the season with colorful decorations, displays, lights, and holiday music in the air.
HOLIDAY-THEMED PHOTO STATIONS
Multiple holiday-themed photo stations providing festive backdrops for holiday photo cards, social media, and to preserve fun memories in pictures!
SWEET TREATS, HOT CHOCOLATE, & MORE!
Indulge in the tastes of the season with a spice latte, a hot chocolate, a caramel Boba tea, peppermint ice cream, holiday chocolates, etc. – and gingerbread galore and the cafés and bakeries downtown.
PET FRIENDLY
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!
SELECT DOWNTOWN ROADS CLOSED – PEDESTRIAN ONLY MARKET
West Plant Street from Dillard Street to Park Avenue, as well as adjoining side streets, will be CLOSED for the Holiday Market, providing a pedestrian only, convenient way to enjoy downtown.
The road closures are in effect from December 1 at 2:00 pm through December 2 at approximately 11:00 pm.
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.).
Please note that 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.
WARNING of Fraudulent Online Solicitation: Please note that the City of Winter Garden is NOT soliciting outside vendors 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 a City event, it is fraudulent solicitation and do NOT engage in providing information or any form of payment.