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SHOP, DINE & STROLL RAFFLE MAY-NIA & LIVE MUSICSaturday, May 2, 2026
9:00 am – 10:00 pm
Winter Garden Downtown Historic District
Public: This event is open for all.
Feeling lucky? Raffle MAY-nia hits downtown at the annual SHOP, DINE & STROLL on Saturday, May 2, with chances to win multiple prizes at your favorite shops and restaurants in addition to a grand prize cash gift card.
Hosted by the downtown merchants and the City of Winter Garden, SHOP, DINE & STROLL 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.
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. (Plus, easy online form to enter drawings by scanning the QR code on the raffle tickets.)
TOTE BAG GIVEAWAY
A commemorative event reusable tote bag will be awarded to the first 20 customers that 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. Another opportunity to win a prize!
LIVE MUSIC, 11:00 am – 7:00 pm
Centennial Plaza
SAMMY VELEZ | 11:00 am – 2:30 pm
Sammy Vélez has been a mainstay in Latin music for decades, first garnering acclaim touring the world with legendary groups like Menudo, Tommy Torres, and Pedro Capó. Now based in
Orlando, Sammy continues to evolve his sound while highlighting his Puerto Rican roots.
EARTHTONEZ TRIO | 3:30 – 7:00 pm
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 – Always!
Convenient public parking is always free throughout Downtown Winter Garden including, for example, along West Plant Street, 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.
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.
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Event Venue
Winter Garden Downtown Historic District, Winter Garden, Florida, United States
Tickets
Concerts, fests, parties, meetups - all the happenings, one place.
