Treat Yourself to Festive Fun at Downtown Winter Garden Small Business Saturday Event

October 22, 2025

The Small Business Saturday event happens on Saturday, November 29th, and it’s the best reason to get the family out to explore the charming streets of downtown Winter Garden over Thanksgiving weekend. The beautiful brick-lined streets will be transformed into a festive wonderland complete with live music as the community celebrates its unique downtown shops for the nationally observed holiday. It’s the perfect way to make new memories while taking part in a celebration of community and cozy small-town fun.

Kick Off Holiday Shopping

Begin the day by visiting local mom-and-pop shops that make Winter Garden a premier destination and check out the sidewalk sale outdoor racks and tables for some early holiday shopping. You’ll find everything from boutique apparel and jewelry to home décor, gourmet foods, sporting gear, pet supplies, and more—each shop with its own personality and local touch.

Capture some Holiday Magic 

Downtown Winter Garden is always a festive environment for the holidays. Come get a sneak peek at downtown’s merry decorations and great holiday photo ops.

Live Music All Day Long 

Free live music will fill the streets with feel good sounds from 11 a.m. to 7 p.m. at the Centennial Plaza stage.

Kick off your afternoon with Red Mint (11 a.m.–2:30 p.m.), whose blend of pop, jazz, and Brazilian bossa nova brings a breezy energy that’s perfect for a sunny Florida afternoon. Later in the day, Joey & Danielle (3:30–7 p.m.) take the stage with a mix of rock, pop, and country favorites, which makes for an ideal soundtrack for your early evening stroll as the lights begin to twinkle across the historic district. 

Eat, Sip, and Treat Yourself

Shopping and dancing to live music will surely mean you need time to refuel. Just step in any direction, and you will find a variety of dining options including coffee houses, farm-to-table restaurants, bakeries, ice cream parlors, chocolate shops, and even a craft brewery for a well-deserved break. Grab a latte and a pastry on a patio surrounded by holiday decor and twinkling lights or enjoy lunch alfresco while local musicians play nearby.

Why Shopping Small Matters

When you shop, dine, and enjoy this special event, you’re supporting neighbors, creators, and dreamers who make this community so unique. You’re also keeping your money in your local economy. 

 Event Details at a Glance

• Event: Downtown Winter Garden Small Business Saturday Sidewalk Sale
• Date: Saturday, November 29, 2025 (Rain or Shine)
• Location: Historic Downtown Winter Garden
• Farmers Market 8 a.m. – 1 p.m. (Downtown Pavilion, 104 S. Lakeview Ave)
• Live Music: 11 a.m. – 7 p.m. (Centennial Plaza Gazebo)
  • Red Mint Duo – 11 a.m. – 2:30 p.m.
  • Joey & Danielle Duo – 3:30 p.m. – 7 p.m.
• Parking: FREE throughout downtown

 Participation, promotions, and operating hours vary per business.