Annual Summer Sidewalk Sale Combines Savings with Entertainment

July 2, 2025

Looking for something fun to do in downtown Winter Garden as the summer season comes to an end? Mark your calendar for Saturday, August 2, 2025, and experience one of the season’s most exciting events: the Annual Summer Sidewalk Sale! This all-day event offers the perfect mix of bargain shopping, free kid treats/activities, live music, and local eats — all in the heart of historic downtown Winter Garden.

SUPPORT LOCAL WITHIN DOWNTOWN WINTER GARDEN’S SCENIC STREETS

Explore the charming, brick-lined streets of downtown Winter Garden during this outdoor shopping event, where dozens of local boutiques, specialty stores, and small businesses roll out sale racks and tables filled with end-of-season closeout markdowns on clothing, accessories, shoes, home décor, gifts, and more. Many shops will also offer exclusive in-store promotions, so don’t forget to step inside and browse!

Don’t miss any deals — be sure to check out the side streets of downtown Winter Garden, where hidden gems await.

BACK TO SCHOOL TAX HOLIDAY – Extra Savings!

The timing of our Sidewalk Sale coincides with Florida’s Back to School Holiday! Stack your savings with tax-free shopping on items eligible for the Back to School Sales Tax Holiday! This includes apparel, footwear, and accessories priced $100 or less. For a list of qualifying tax-exempt items, visit floridarevenue.com/BacktoSchool.

LINGER DOWNTOWN AND ENJOY FREE LIVE MUSIC

Live Music Schedule:

The Absent Trio: 11:00 a.m. – 2:30 p.m. (Pop & Rock)
L&G Live: 3:30 p.m. – 7:00 p.m. (Acoustic, 90s Hits, Pop-Punk)

These talented local musicians will provide the perfect soundtrack of pop, soft-rock, punk rock, and 90s hits as you stroll by, or take a break and hang out in Centennial Plaza.

FREE KID-FRIENDLY ACTIVITIES IN DOWNTOWN WINTER GARDEN

Families looking for free things to do with kids in Winter Garden will love these special offerings:

Free Treat on Main Street (10:00 a.m. – 2:00 p.m.): Kids 12 and under can choose between fresh-squeezed lemonade from Bryan’s Lemonade or a flavorful Italian Ice. Stop by the booth on South Main Street — one treat per child while supplies last.

Free Back to School Craft (9:00 a.m. – 1:00 p.m.): Hosted by SOBO Art Gallery at 127 S. Boyd Street, this outdoor craft station lets K-12 students create their own custom zippered pencil case — a fun and useful project to kick off the school year!

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

Hungry after racking up all those savings? Downtown Winter Garden is home to some of the best local restaurants, cafes, ice cream shops, and bakeries in Central Florida. Enjoy a wide variety of cuisines including Italian, Mexican, Indian, Thai, German, Japanese, and more!

Choose from cozy indoor dining or scenic outdoor patio seating with umbrellas and shade — all just steps from the action.

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.), the Downtown Pavilion, 104 S. Lakeview Ave., the City Hall parking lot (300 W. Plant St.), and along West Plant Street.

LOVE LOCAL

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!

PLAN YOUR DAY IN DOWNTOWN WINTER GARDEN

Whether you’re a local or visiting from nearby Orlando, the Downtown Winter Garden Summer Sidewalk Sale is one of the best free events in Central Florida. Come out and enjoy a day filled with shopping deals, live entertainment, and family-friendly fun in one of the most walkable and picturesque towns in Florida.

This is a Rain or Shine event. Participation and store hours vary by merchant.