Downtown Winter Garden Summer Sidewalk Sale & Live Music
Saturday, August 2, 2025
All Day
Winter Garden Downtown Historic District
Winter Garden, FL 34787
Participation, sales, special offers, and operating hours are at the sole discretion of the individual businesses and vary per merchant. A rain or shine event.
SIDEWALK SALE
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 (per Florida Department of Revenue).
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.
LIVE MUSIC SCHEDULE: 11:00 am - 7:00 pm │ Free
Performing at Centennial Plaza in the center of downtown, enjoy the outdoor music concert and the fun vibe!
The Absent Trio │ 11:00 AM – 2:30 PM
THE ABSENT TRIO is 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 - 7:00 PM
L&G LIVE is 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.
FREE TREAT ON MAIN STREET for Kids │11:00 am – 2:00 pm
Kids 12 and under are treated to a FREE treat - stop by the tented booth located on South Main Street from 11:00 am to 2:00 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 │9:00 am – 1:00 pm
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, 9:00 am – 1:00 pm or while supplies last).
DINING
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.
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 City Hall parking lot (300 W. Plant St.), along West Plant Street, and
more.
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!
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.
Also check out other Music events in Winter Garden, Entertainment events in Winter Garden, Kids events & activities in Winter Garden.
