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Small Business Saturday Sidewalk Sale with Live MusicSaturday, November 29, 2025
ALL-DAY
Location: Historic Downtown Winter Garden
Kick off your holiday shopping at festive Downtown Winter Garden with a SMALL BUSINESS SATURDAY SIDEWALK SALE & LIVE MUSIC!
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
Red Mint: 11:00 am – 2:30 pm (pop, jazz, Brazilian bossa nova)
Joey & Danielle Duo: 3:30 pm - 7:00 pm (jazz, rock, country, pop, dance, top 40)
Come early to stop by the Winter Garden Farmers Market and support its small business vendors (8:00 am – 1:00 pm).
The Downtown Small Business Saturday Sidewalk Sale will be held rain or shine.
Sales, special offers, and operating hours vary per merchant.
Thank you for SHOPPING SMALL to HELP BIG!
PARKING – Always FREE!
Convenient public parking is always free throughout Downtown Winter Garden, including at the
three-level parking garage (160 S. Boyd St.), 117-space parking lot (37 N. Boyd St.), City Hall (300 W. Plant St.), along West Plant Street, etc.
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.
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Event Venue & Nearby Stays
Winter Garden Downtown Historic District, 127 S Boyd St, Winter Garden, FL 34787-3501, United States
Concerts, fests, parties, meetups - all the happenings, one place.
