- December 4, 2025
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If you’re in need of a little retail therapy, make sure you head to downtown Winter Garden this weekend.
The Downtown Winter Garden Summer Sidewalk Sale takes place from 10 a.m. to 10 p.m. Saturday, Aug. 2.
Take advantage of end-of-season clearance closeout prices on boutique originals. Stroll the outdoor sale racks and tables and pop inside the shops for additional sales and promotions.
Stack your savings with tax-free shopping on items eligible for the back-to-school sales tax holiday. Qualifying tax-exempt items include apparel, footwear, and handbags priced at $100 or less.
The event also will feature live music from 11 a.m. to 7 p.m. at Centennial Plaza. The Absent Trio performs from 11 a.m. to 2:30 p.m., and L&G Live from 3:30 to 7 p.m.
The event also will include free treats from Bryans Lemonade for kids from 11 a.m. to 2 p.m., as well as a free back-to-school kids craft from 9 a.m. to 1 p.m. hosted by SOBO Art Gallery, 127 S. Boyd St.. Swing by the gallery's outdoor patio to make a custom-designed, zippered, cloth pencil case for the new school year.