Celebrate the End of Summer at the Annual Downtown Winter Garden Summer Sidewalk Sale

July 3, 2024

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. Our local shops always host 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 Summer Sidewalk Sale on Saturday, August 3, 2024, 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. 

SUPPORT LOCAL WITHIN DOWNTOWN WINTER GARDEN’S SCENIC STREETS 

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. Look for the outdoor Summer Sidewalk Sale along the main drag of Plant Street, in addition to on all the adjoining side streets in downtown — make sure to explore each one and see what awaits.

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. Participation, sales, special offers, and operating hours are at the sole discretion of the individual businesses and vary per merchant.

BACK-TO-SCHOOL TAX HOLIDAY

Make sure to take full advantage of the timing of the Summer Sidewalk Sale, as it coincides with the tax-free holiday! Stack your savings with tax-free shopping on items eligible for the Back to School Sales Tax Holiday! If you need clarification on what qualifies, visit floridarevenue.com/BacktoSchool for a list of qualifying tax-exempt items. 

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!

LINGER DOWNTOWN AND ENJOY FREE LIVE MUSIC

We are setting the soundtrack to your shopping journey all day! 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! A downtown favorite, Mud Rooster kicks up the downtown vibe a notch from 11 a.m. to 3 p.m. with a high energy performance of their funky and stylish takes on the blues, rockabilly, and classic rock greats. Up next from 4 p.m. to 7 p.m., the brother bandmates of American Jones will turn onlookers into adoring fans. The easy listening duo with a soul-rock vibe have a following around the world. Patrons to downtown are in for a treat with these two performances!

MUSIC SCHEDULE:

Mud Rooster (Blues / Roots / Jazz) │ 11 a.m. – 3 p.m. 

American Jones (Easy Listening) │4:00 – 7:00 p.m.

FREE GELATO FOR KIDS ON MAIN STREET 

You won’t have any problem getting the kids to come along on your shopping trip with the promise of a FREE gelato – the perfect summer treat! Kids 12 and under are invited to stop by the remote Gelato Cart located on South Main Street during the Summer Sidewalk Sale for the complimentary delectable, icy dessert (one free gelato per child), available from 11 a.m. to 4 p.m. or while supplies last. Gelato is available for adults to purchase. (Gelato is provided by Downtown’s own Mangoni Italian Market Pizza restaurant.)

FREE BACK-TO-SCHOOL KIDS CRAFT

Kids are invited to create a personally-designed canvas pencil case free-of-charge at the art tent located at the SOBO Art Gallery front patio, 127 S. Boyd St. (across from the parking garage). Stop by from 10 a.m. to 2 p.m. to make this handy custom creation to hold school supplies. Conducted by a certified art instructor, the activity is provided courtesy of the Winter Garden Art Association in collaboration with the City of Winter Garden.

FUEL YOUR SHOPPING WITH LOCAL EATS AT ONE OF OUR LOCAL RESTAURANTS 

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 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.).