Jump into May with daylong Shop, Dine & Stroll

The city of Winter Garden and the downtown merchants are hosting a day of shopping, raffles live music and dining Saturday, May 3.

By Amy Quesinberry Price
| 10:29 a.m. April 30, 2025

Arts + Entertainment
Things to Do

If you’re looking for a new spring wardrobe, or you just like hanging out in downtown Winter Garden, this Saturday, May 3, is the “Shop, Dine & Stroll Raffle May-nia & Live Music” event.

The daylong event features a downtown-wide raffle, outdoor live music concerts, a commemorative tote bag giveaway, shopping and dining options and more. It is hosted by the downtown Winter Garden merchants and the city of Winter Garden.

The more you shop, the more chances you will have of winning one of the many raffle prizes. Raffle participation and in-store promotions will vary by merchant.

To commemorate the event, the first 1,000 event-goers will receive a free reusable tote bag. Stop by the event booth at Centennial Plaza from 11 a.m. to noon to pick up a bag (one per family, while supplies last).

If you enjoy live music, Sarah and Steven Cardwell, a Central Florida indie-folk duo who make up the group Crenshaw, will play from 11 a.m. to 3 p.m. and acoustic loop artist Brad Kriebel will perform from 4 to 8 p.m.

author

Amy Quesinberry Price

Community Editor Amy Quesinberry Price was born at the old West Orange Memorial Hospital and raised in Winter Garden. Aside from earning her journalism degree from the University of Georgia, she hasn’t strayed too far from her hometown and her three-mile bubble. She grew up reading The Winter Garden Times and knew in the eighth grade she wanted to write for her community newspaper. She has been part of the writing and editing team since 1990.