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Small Business Saturday Celebration: Sidewalk Sale & Live MusicSaturday, November 28, 2026
ALL-DAY
Location: Historic Downtown Winter Garden
What better way to kick off your holiday shopping then at festive Downtown Winter Garden – a 2026 Official Hallmark Christmas Town! Join us for a SMALL BUSINESS SATURDAY
CELEBRATION including a SIDEWALK SALE & LIVE MUSIC on Saturday, November 28.
The mom-and-pop shops in historic downtown make this a must-stop to observe the national holiday. Stroll and shop the outdoor racks while enjoying the holiday vibe. Be sure to also pop inside the shops for even more gift ideas.
Great holiday photo ops too with merry decorations throughout downtown!
LIVE MUSIC SCHEDULE: 11:00 AM - 7:00 PM
CENTENNIAL PLAZA GAZEBO
PhoeNyx: 11:00 am – 2:30 pm (‘80s, current pop, rock, RBB)
EarthTonez Trio: 3:30 pm - 7:00 pm (soul, jazz, alternative, hip hop)
MAIN STREET / GARDEN MUSIC SCHOOL, 40 S. Main Street.
Acoustic Solo: 12:00 – 2:00 pm
The Downtown Small Business Saturday Sidewalk Sale will be held rain or shine.
Sales, special offers, and operating hours vary per merchant.
WINTER GARDEN FARMERS MARKET, 8:00 am – 1:00 pm
Come early to stop by the Winter Garden Farmers Market and support its small business vendors.
PARKING – FREE!
Convenient public parking is free throughout downtown, including at:
Downtown Parking Garage (three levels), 160 S. Boyd St
37 N. Boyd Street Parking Lot
Winter Garden City Hall, 300 W. Plant St.
695 W. Plant Street Parking Lot
Sam Williams Little League Complex, 415 S. Park Ave.
Veterans Memorial Park, 420 S. Park Ave.
S. Woodland St. & E. Joiner St. (2 parking lots on either side of S. Woodland St.)
Behind Winter Garden Post Office (off N. Lakeview Ave. between W. Plant St. and W. Newell St.)
W. Bay St. and N. Highland Ave. Parking Lot
WHAT IS SMALL BUSINESS SATURDAY?
Small Business Saturday takes place annually on the Saturday after Thanksgiving and encourages shoppers to “shop small” by supporting local, independently owned businesses. It
started as a campaign by American Express in 2010 to remind shoppers to support the smaller, lesser-known businesses in your local community; and in 2011, the U.S. Senate passed a
resolution to support the day.
The impact of Small Business Saturday not only helps small business owners but also supports local communities with $68 of every $100 spent remaining local.
Thank you for SHOPPING SMALL
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Event venue
300 W. Plant Street, Winter Garden, FL, United States, Florida 34787
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Concerts, fests, parties, meetups — all the happenings, one place.