top of page
  • Writer's pictureGotta Go Orlando

Shop, Dine & Stroll returns to downtown Winter Garden, bigger and better than ever before

The daylong event in historic downtown Winter Garden will be a fun time to share with friends, a date, or mom for an early Mother’s Day celebration.

Shop, Dine & Stroll returns to downtown Winter Garden

Mark your calendars for a special all-day event on Saturday, May 4 in downtown Winter Garden. Shop, Dine & Stroll is back bigger and better than ever before.

The downtown streets will be filled with the sound of live music, and while you shop and dine, you will be participating in RAFFLE "MAY"NIA! for chances to win prizes from participating businesses, PLUS a downtown-wide GRAND PRIZE DRAWING up to $500!

SHOP, DINE & STROLL on Saturday, May 4, is the perfect spring outing to relish the outdoors and flowering scenery while live music fills the air. It’s a chance to discover unique shopping and dining options and win great prizes in multiple raffles.

Music will fill the air as you SHOP, DINE & STROLL when special live performances take center stage at Centennial Plaza. Grab a nearby swing, bench, or outdoor table for a front row seat. The free outdoor concert features two popular local bands: Hanger 61 and Mud Rooster.

Shop, Dine & Stroll returns to downtown Winter Garden

The excitement of Raffle “May”nia has struck downtown with chances to win prizes at shops and restaurants in addition to a grand prize of cash gift cards!

For EVERY $25 spent at a participating store or restaurant, a shopper earns one entry into that establishment’s raffle (max. 10 tickets per customer, per store).

Each participating business will conduct a raffle drawing for in-store gift cards or merchandise, and then all downtown entries (including the winners’ tickets) will be combined and entered in a grand prize drawing to win $500, $250, and $100 Visa gift cards.

The more purchases you make, the more entries you earn; and the more places you patronize…the more chances you have to win multiple prizes.

Look for the raffle ticket sign in the windows of participating businesses, and “May the Fourth Be with You” for good luck!

For more information on SHOP, DINE & STROLL, check out Downtown Winter Garden's website.

Shop, Dine & Stroll returns to downtown Winter Garden

Gotta Go Orlando is committed to offering locals and visitors the best coverage of things to do in Orlando, and Central Florida, including the latest entertainment news, live music, theater, nightlife, food & drink. theme parks, attractions, events, culture, and more.

For the latest entertainment news and things to do in Orlando, and throughout Central Florida, join us on X, Facebook, Instagram, and YouTube.

Never miss any Orlando news! Sign up to the Gotta Go Orlando Newsletter.

Got a story to tell? Contact us here. To advertise with us, click here, and to list your upcoming event with us, submit it here.


bottom of page