Summer Sidewalk Sale Brings Boutique Bargains and Live Music

July 13, 2026

Get ready for a full day of shopping, live entertainment, family fun, and local flavor at Downtown Winter Garden’s Summer Sidewalk Sale!

Spend the day exploring the charming historic streets as local merchants bring their best bargains outdoors. From apparel and accessories to footwear, home décor, gifts, and more, you’ll find incredible deals on sale racks and tables lining West Plant Street, Main Street, and Boyd Street. Be sure to step inside participating shops for even more exclusive promotions and summer clearance specials.

Make your savings go even further by taking advantage of Florida’s Back-to-School Sales Tax Holiday on qualifying items, including apparel, footwear, and handbags priced at $100 or less.

Shop, Stroll & Enjoy Live Music

The festive atmosphere comes alive with free outdoor entertainment throughout the day.

Centennial Plaza Gazebo (Center of Downtown)

11:00 a.m. – 2:30 p.m. | CRENSHAW – An indie folk duo known for heartfelt harmonies, charming storytelling, and unforgettable melodies.
3:30 p.m. – 7:00 p.m. | MALCANTHEARYOU – Orlando’s inspiring powerhouse vocalist whose music has gained international recognition. Born deaf, Mal continues to inspire audiences through talent, determination, and resilience.

Garden Music School (40 S. Main Street)

12:00 – 2:00 p.m. | ACOUSTIC SOLO – Enjoy an acoustic solo performance from talented Garden Music School musicians.

Family Fun

From 9:00 a.m. to 1:00 p.m. (while supplies last), stop by SOBO Art Gallery for a free Back-to-School Kids’ Craft. K–12 students can design their own zippered cloth pencil case to kick off the new school year. One free craft per student.

Take a Break & Dine Local

After scoring great deals, recharge at one of Downtown Winter Garden’s many locally owned restaurants, cafés, bakeries, ice cream shops, or brewery. Whether you’re looking for a quick bite or a leisurely meal on one of the outdoor patios, there’s something to satisfy every craving.

Free Parking

Enjoy complimentary public parking throughout Downtown Winter Garden, including the three-level parking garage, City Hall parking lot, public lots, and convenient street parking.

Shop Local. Support Local.

Every purchase you make supports the independent businesses that make Downtown Winter Garden such a special destination. Shopping local helps strengthen our community and keeps more dollars invested right here at home.

Bring your family, invite your friends, and spend the day shopping, dining, listening to live music, and celebrating everything that makes downtown Winter Garden unique.