Shop, Dine & Stroll with Live Music & Raffle “May”nia

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. 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.


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.

Music Schedule:

HANGER 61  (Electric Rock Band) │11:00 am – 3:00 pm
Fasten your seatbelt and take flight with Hanger 61 as it provides a musical adventure with crowd-pleasing, eclectic mix of songs in an authentic “from the heart” way. The group will have the audience singing along to well-known hits and deep cuts across a variety of genres.

MUD ROOSTER (Blues/Roots/Jazz) │ 4:00 – 8:00 pm 
Rocking local establishments for 15 years, Mud Rooster brings their funky and stylish takes on the blues, rockabilly, and classic rock greats to downtown Winter Garden. Their high energy performance will have the crowd on their feet!


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!


It is the perfect time to update your wardrobe, accessories, and home décor; stock up on your favorite gourmet provisions; and take advantage of special promotions during the one-day SHOP, DINE & STROLL. You never know what unique finds await, so be sure to visit both your trusty shops as well as explore new ones. 


From casual restaurants, coffee cafes, bakeries, and ice cream parlors to fine dining and even a local brewery, there are dining options for all tastes and interests adding to the fun downtown experience. The numerous outdoor dining tables provide a convenient way to soak up the lush scenery as well as a side of sunshine with your meal.


Stroll the streets of historic downtown surrounded by small town charm, beautiful sights, lush foliage, and spring flowers. Hum along to the musical tunes in the air as you walk up and down the brick-lined streets taking in the sights and sounds. From 8 a.m. to 1 p.m., you can stroll through the award-winning Winter Garden Farmers Market taking place right in downtown for a vast selection of fresh produce and artisan goods. Enjoy the downtown vibe while getting steps into your day.


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 at Winter Garden City Hall (300 W. Plant St.).


SHOP, DINE & STROLL is a great way to show support for the downtown businesses that make Winter Garden so unique! 

Small, locally owned businesses are a vital part of the United States economy and the backbone of a local community. For every dollar spent locally, 68 cents stay in the local community while only 30-40 cents stay local when shopping at a national retailer.

Shop, Dine & Stroll will be held rain or shine. Operating hours, sales, and promotions vary per merchant. Raffle participation and guidelines are at the discretion of individual establishments. You do not need to be present for the raffle drawings to win. Winners of in-store raffle drawings will be notified by individual businesses. Winners of the Grand Prize raffle drawing of Visa Gift Cards will be notified by the City of Winter Garden no later than Friday, May 10, 2024.


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