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SHOP, DINE & STROLL RAFFLE MAY-NIA & LIVE MUSICSaturday, May 3, 2025
9:00 am – 10:00 pm
Winter Garden Downtown Historic District
Public: This event is open for all.
A perfect spring outing, you won’t want to miss SHOP, DINE & STROLL on Saturday, May 3, in quaint historic downtown Winter Garden. The annual event features live music, a downtown-
wide Raffle MAY-nia with the opportunity to win multiple prizes at shops & restaurants in addition to a grand prize cash gift card, free commemorative tote bag giveaway (while supplies last), unique dining & shopping options, blooming spring scenery, and so much more.
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.
LIVE MUSIC OUTDOOR CONCERT, 11:00 am – 8:00 pm
Centennial Plaza
CRENSHAW (Indie-Folk duo) | 11:00 am – 3:00 pm
The strong harmonies and quirky, yet thoughtful songwriting of Indie-Folk duo Sarah and Steven Cardwell of Crenshaw easily captures fans with their music that you will want to listen to again and again.
BRAD KRIEBEL (Acoustic Loop) | 4:00 – 8:00 pm
The Acoustic Loop Artist Brad Kriebel is known for his heartfelt performances that connect deeply with audiences with his soulful sound that blends elements of Pop, Alt, and R&B into unique covers of classic and contemporary hits.
FREE REUSABLE TOTE BAG GIVEAWAY, 11:00 am – 12:00 pm
Centennial Plaza
A commemorative reusable tote bag will be given to the first 1,000 event goers from 11:00 am to 12:00 pm at Centennial Plaza (while supplies last, one bag per family). What's more -- randomly selected tote bags will include a $20 cash gift card to kick off your shopping spree!
RAFFLE MAY-NIA
How the Raffle Works:
1. Shop & Dine Local, Earn Entries
Every participating business will host its own raffle for a gift card or prize.
Prize value depends on the type of business:
SHOP & DINE merchants: $50 minimum prize
STROLL merchants: $25 minimum prize
2. How to Earn Raffle Tickets:
SHOP & DINE Merchants (retail stores and restaurants):
Spend $25 = 1 raffle ticket
Max 10 tickets per transaction
STROLL Merchants (coffee shops, ice cream parlors, bakeries):
Spend $10 = 1 raffle ticket
Max 5 tickets per transaction
The more places you shop and/or dine — and the more you spend — the more entries and chances you have to win prizes!
BONUS JACKPOT DRAWING:
After the individual business raffles, all tickets (including winning tickets) go into a Grand Prize Jackpot drawing.
Prizes:
1 winner of a $500 Visa gift card
2 winners of $250 Visa gift cards
2 winners of $100 Visa gift cards
You can win at one store, multiple stores, and also in the Grand Prize drawing!
ADDITIONAL INFO:
Max 10 tickets per SHOP & DINE merchant per transaction
Max 5 tickets per STROLL merchant per transaction
You don’t need to be present to win
Winners will be posted online on Friday, May 9, 2025, on www.cwgdn.com. (Winning Raffle Ticket Stub must be presented when claiming prize.)
FREE PARKING – Always!
Convenient public parking is always free throughout Downtown Winter Garden including 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.).
LOVE LOCAL
SHOP, DINE & STROLL RAFFLE MAY-NIA is a great way to show support for the downtown Winter Garden businesses that make our community so unique!
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 & Nearby Stays
Winter Garden Downtown Historic District, 127 S Boyd St, Winter Garden, FL 34787-3501, United States,Winter Garden, Florida
Tickets
USD 0.00
