Shop, Dine & Stroll Brings Raffle MAY-nia & Live Music to Downtown

April 27, 2026

Spring in Central Florida has a way of turning even an ordinary Saturday into something worth celebrating—and on May 2, historic downtown Winter Garden is dialing that feeling all the way up with its annual Shop, Dine & Stroll: Raffle MAY-nia & Live Music event.

From the moment the day begins, the brick-lined streets will hum with a kind of cheerful energy that only comes from sunshine, music, and the promise of a little friendly luck. Whether you’re browsing for the perfect Mother’s Day gift, refreshing your wardrobe, or just looking for an excuse to wander outdoors, this all-day event blends leisure, local flavor, and a dash of excitement.

A Stroll with a Side of Serendipity

At the heart of the festivities is Raffle MAY-nia, a playful twist on your typical shopping day. The concept is simple: the more you explore, the more chances you have to win. Every purchase—big or small—earns raffle tickets, and every ticket is another shot at winning a prize.

Spend a little, get a ticket. Spend more, stack your odds. Hop between boutiques, cafés, and restaurants, and suddenly your afternoon outing turns into a mini treasure hunt. Each participating business (look for raffle ticket in window) will award its own prize (valued at $50 or more), and then—just when you think the fun is over—every ticket goes back into the mix for the grand prize drawings.

And those grand prizes? Think gift cards worth $500, $250, and $100—perfect for fueling your next shopping spree. RAFFLE DETAILS

Tote Bags, Treats, and Tiny Thrills

Adding to the excitement is a charming perk for early birds: the first 20 shoppers at each participating retail store will receive a commemorative tote bag. But here’s the twist—one lucky bag at each store contains a hidden $20 gift card. It’s a small surprise that captures the spirit of the day: you never quite know what delightful bonus might be waiting around the corner.

The Soundtrack of the Day

No spring gathering is complete without music drifting through the air, and this event delivers with a full lineup of live performances at Centennial Plaza.

Expect vibrant Latin rhythms from Sammy Vélez in the late morning and early afternoon (11 a.m. – 2:30 p.m.), followed by the soulful, genre-blending sounds of EarthTonez Trio into the evening (3:30 – 7 p.m.). Whether you’re pausing on a shaded bench or simply passing by mid-stroll, the music becomes part of the atmosphere—an easygoing soundtrack to your day downtown.

Shop, Sip, Savor, Repeat

Between raffle entries and music breaks, the real joy lies in the experience itself. Pop into locally owned shops filled with unique finds, from home décor to fashion. Step into a cozy café for an iced latte or linger over a leisurely lunch at an outdoor table surrounded by blooming flowers. Maybe end your day with something sweet—ice cream in hand as the sun dips lower over Plant Street. There’s no rush, Shop, Dine & Stroll is an invitation to slow down, explore, and enjoy. And with free parking throughout downtown, getting there—and staying awhile—is refreshingly easy.

Whether you bring a friend, pack the family in the car, or relish a day to yourself, be sure to leave a little room in your plans for spontaneity—you might just walk away with more than you expected.

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.