Save the Date for the Annual Downtown Winter Garden Summer Sidewalk Sale

The popular event features participating stores with sidewalk sales racks, and more, so set a reminder to shop, support, and save!

As summer winds down in downtown Winter Garden and residents and locals prepare for the fall season, the local mom-and-pop shops invite all to stroll the bustling sidewalks for sales, live music, and family fun. Discover unique treasures, from home goods, gifts, jewelry, clothing, home décor, and more.

The warm sunshine and friendly faces of local shopkeepers create a welcoming atmosphere, making the annual Downtown Summer Sidewalk Sale on Saturday, August 2, 2025, a perfect outing for families and friends. 

Whether you’re hunting for a unique gift or simply enjoying the lively ambiance, sidewalk sales offer an excellent way to support small businesses and discover the heart of the community. Even better than treating yourself to a day of shopping and supporting locals is taking advantage of end-of-season clearance prices that you won’t want to miss out on. 

The event in scenic downtown is a fun summertime outing for all! Grab your shopping tote, put on some sunscreen and your best walking shoes, and explore all the local shops that make Downtown Winter Garden a premier shopping destination.

The annual sidewalk sale is the ideal time to visit each store and snag bargains on those unique, one-of-a-kind items that can only be found at downtown specialty stores.

Look for the outdoor Summer Sidewalk Sale along West Plant Street stretching from Woodland Street to Central Avenue, as well as along adjoining Main Street and Boyd Street.

Leave no rack and table undiscovered for many bargains on apparel, accessories, footwear, home goods, and more at discounted prices. If there is something you’ve had your eye on at one of these shops, now is the time to visit and see if it’s now a part of a sale or promotion!

BACK-TO-SCHOOL TAX HOLIDAY

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 (per Florida Department of Revenue).

LINGER DOWNTOWN AND ENJOY FREE LIVE MUSIC

You can search downtown for the best deals with fantastic live music from centrally located Centennial Plaza! When you need a shopping break, sit, and enjoy!

The Absent Trio: 11 AM - 2.30 PM

A crowd favorite duo comprised of the vocal/guitar stylings of Allie Sawicki & and the bass/percussion/vocal stylings of Noel Kunz. These versatile musicians have a repertoire spanning a broad range of genres such as pop and rock and their unique presentation makes them even more impressive to watch.

L&G Live: 3:30 pm - 7 pm

An acoustic duo that is made up of a blend of acoustic guitar, Cajón, and tight harmonies. This fun-loving duo performs uproarious pop, soft-rock, punk rock, and 90s hits. L&G LIVE’s roof-raising repertoire and rich and resonant vocal tones will have everyone singing and dancing along.

FUEL YOUR SHOPPING WITH LOCAL EATS

Searching for the best sales works up quite the appetite. Make sure to take a shopping break at one of the many downtown dining options: sit-down and quick-service restaurants, cafes, bakeries, ice cream shops, and even a brewery.

Downtown’s culinary scene offers Indian, Italian, Mexican, Thai, and German cuisines, to name a few! Grab a bite inside to cool down, or enjoy the many outdoor dining patios with tables, chairs, and umbrellas that are conveniently located throughout downtown amidst the beautiful scenery.

FREE TREAT FOR KIDS ON MAIN STREET 

Kids 12 and under are treated to a FREE treat - stop by the tented booth located on South Main Street from 11 am to 2 pm for a complimentary FRESH-SQUEEZED lemonade by Bryans Lemonade in choice of flavors or an Italian Ice (one free treat per child, while supplies last).

FREE BACK-TO-SCHOOL KIDS CRAFT

K-12 students will enjoy a FREE back-to-school craft project hosted by SOBO Art Gallery, 127 S. Boyd Street. Swing by the Gallery's outdoor patio to make a custom-designed, zippered, cloth pencil case for the new school year (no charge, one per student, 9 am – 1: pm or while supplies last).

FREE PARKING – Always!

Convenient parking is always free throughout Downtown Winter Garden, including at

the City’s three-level parking garage (160 S. Boyd St.), the 117-space parking lot (37 N.

Boyd St.), and the City Hall parking lot (300 W. Plant St.).

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