- April 29, 2026
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If you’re in need for some retail therapy, downtown Winter Garden is the place to be this weekend.
Downtown Winter Garden will host its Shop, Dine and Stroll event from 9 a.m. to 10 p.m. Saturday, May 2, in downtown Winter Garden.
Hosted by the downtown merchants and the city of Winter Garden, this event is sure to be a fun day for all. Whether you are shopping for upcoming Mother's Day and graduations; wanting to refresh your wardrobe and home for spring and summer; or looking for a fun event to enjoy the blooming spring scenery and weather, this event is sure to satisfy.
RAFFLE MAY-NIA
Look for the raffle ticket displayed in the window of participating stores and restaurants. With any purchase, a raffle ticket is awarded. Then, with every $25 spent, an additional raffle ticket is awarded. You can win at multiple shops and restaurants and win a grand prize cash gift card up to $500.
TOTE BAG GIVEAWAY
A commemorative event reusable tote bag will be awarded to the first 20 customers who make a purchase at each participating retail store. In addition, one of the 20 tote bags includes a $20 store gift card for that shop.
LIVE MUSIC
Sammy Vélez will perform from 11 a.m. to 2:30 p.m. at Centennial Plaza. Vélez has been a mainstay in Latin music for decades, first garnering acclaim touring the world with legendary groups such as Menudo, Tommy Torres, and Pedro Capó. Now based in Orlando, he continues to evolve his sound while highlighting his Puerto Rican roots.
EarthTonez Trio will perform from 3:30 to 7 p.m. at Centennial Plaza. EarthTonez Trio is a vibrant and dynamic band that blends the colors of soul, jazz, alternative, and hip hop to create a kaleidoscope of music experiences. Based in Orlando, this group takes its listeners on a musical journey as passion and emotion shine onstage whether performing original or cover songs.
FREE PARKING
Public parking is always free throughout Downtown Winter Garden, including along West Plant Street; in the three-level parking garage (160 S. Boyd St.); 117-space
parking lot (37 N. Boyd St.); and City Hall (300 W. Plant St.).
Shop, Dine & Stroll will be held rain or shine. Operating hours, raffle participation, and promotions vary per merchant. Participation is at the discretion of the individual establishments.