Downtown Summer Sidewalk Sale – August 26, 2023


Summer Sidewalk Sale
Saturday, August 26, 2023
All Day
Historic Downtown Winter Garden

The Downtown Summer Sidewalk Sale is an ideal time to snag boutique apparel, accessories, home décor, and more at discounted prices! Enjoy the sights and small town charm of downtown while you stroll, shop, and dine. The event is a fun summer outing for locals and visitors alike!

Stroll and shop the OUTDOOR sale racks and tables along the scenic brick-lined streets in historic downtown. Find great deals on all those one-of-a kind items that you have been eyeing, which can only be found at downtown’s unique stores. Take advantage of the summer merchandise on sale, which, as we all know, can be worn year round in Central Florida. Plus, Labor Day gatherings are just around the corner! 

Pop INSIDE the stores for additional sales, promotions, and raffles. The air conditioning is cranking for a dose of chilly air in between enjoying the Florida sunshine. 

Take a shopping break at the multitude of downtown dining options: sit down and quick service restaurants, cafes, bakeries, ice cream shops, and even a brewery. Outdoor dining patios with tables, chairs, and umbrellas are conveniently located throughout downtown amidst the beautiful scenery.

The Summer Sidewalk Sale is held along West Plant Street and the surrounding side streets, stretching from Woodland Street to Central Avenue. 

Make a day of it and come early for the weekly Winter Garden Farmers Market (104 S. Lakeview Ave.), 8:00 am – 1:00 pm.

Summer Sidewalk Sale Flyer

Summer Sidewalk Sale is a rain or shine event.
Participation, sales, special offers, and operating hours are at the sole discretion of the individual businesses and vary per merchant.


Convenient parking is always free throughout Downtown Winter Garden, including at the City’s three-level parking garage (160 S. Boyd St.) and the 117-space parking lot (37 N. Boyd St.).


Downtown Winter Garden is comprised of independent, locally owned businesses that are a vital part of the United States economy, and the backbone of our community. For every $100 spent at a locally owned business, $68 will remain in the local community, versus only $43 when shopping at national chains, according to Independent We Stand. Thank you for supporting Local!



WARNING of Fraudulent Online Solicitation: Please note that the City of Winter Garden is NOT soliciting outside vendors for this event. If you receive correspondence by either a third-party company or the likeness of the City of Winter Garden via email or social media about vending at a city event, it is fraudulent solicitation and do NOT engage in providing information or any form of payment.