Shop, Dine & Stroll Raffle MAY-nia with Live Music

March 28, 2025

Downtown Winter Garden’s annual SHOP, DINE & STROLL returns on Saturday, May 3 — and this year, the rewards for shopping local are bigger than ever! Enjoy a day of browsing charming boutiques, savoring delicious eats, and soaking up live music as spring blooms line the streets. Plus, with chances to win exciting prizes in the downtown-wide Raffle MAY-nia, it’s the perfect way to spend a sunny Florida day. Also, with Mother’s Day just around the corner, it’s the ideal time to find that unique gift or create memories strolling downtown with loved ones.

Shop – Dine – Stroll

Downtown Winter Garden is known for many locally owned places to Shop. Spring is the perfect time to update your wardrobe or find an excellent gift for an upcoming celebration, such as Mother’s Day, Father’s Day, Graduations, and more! Check our list of Downtown Retail Shops.

You need fuel to keep shopping, and there are several options to Dine at, from casual restaurants to fine dining and even a local brewery just steps apart. Check out all your Downtown Dining & Drinks options.

While you Stroll the downtown Winter Garden streets, be sure to pop into the coffee cafes, bakeries, and ice cream parlors to grab a quick refreshment, visit the museums including the free one-day photo booth at the Central Florida Railroad Museum, and take in the historic sights that make it a premier destination for locals and visitors. Get more information on what downtown has to offer.

How to Win Big while Shopping Small

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 Locations (retail stores and restaurants):
  
  • Spend $25 = 1 raffle ticket
    
  • Max 10 tickets per transaction
    
• STROLL Locations (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 Cash Jackpot Drawing:

• After the individual business raffles, all tickets (including winning tickets) go into Grand Cash Prizes drawings.
  
• Grand Cash 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 Cash Prize drawing!

Additional Info:

✅ You don’t need to be present at the raffle drawings to win.
✅ Winners will be posted online on Friday, May 9, 2025, on the City of Winter Garden
website.
✅Must present winning raffle ticket stub to claim prize. Prizes must be claimed no later than June 2, 2025.

Live Music While You Shop, Dine & Stroll

Music will fill the air as you SHOP, DINE & STROLL when special live music performances take center stage in the heart of downtown. Grab a nearby swing, bench, or outdoor table for a front-row seat. The free outdoor concert is provided by the City of Winter Garden to create a memorable experience for all. 

LIVE MUSIC OUTDOOR CONCERT, 11:00 am – 8:00 pm
Centennial Plaza, Center of Historic Downtown

11:00 am – 3:00 pm: CRENSHAW

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.

4:00 – 8:00 pm: Brad Kriebel

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.

Get a FREE REUSABLE TOTE BAG – Giveaway to First 1,000 (plus free $20 gift card jackpot in random bags)

To commemorate the event, the first 1,000 event goers will receive a free reusable tote bag. Stop by the Event table at Centennial Plaza on West Plant Street in center of downtown from 11:00 am to 12:00 pm to pick up a shopping bag (one bag per family, while supplies last).

What’s more — limited, randomly selected tote bags will include a $20 cash gift card to add to the jackpot frenzy! Yet, another opportunity to win a prize!!

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!

Shop, Dine & Stroll Raffle MAY-nia will be held rain or shine. Raffle participation is at the discretion of individual establishments. Operating hours vary per merchant.