Shop, Dine & Stroll – March 25, 2023



Saturday, March 25, 2023

All Day

Historic Downtown Winter Garden

Outdoor Shopping & Dining Experience with LIVE MUSIC in picturesque Historic Downtown 

Winter Garden in celebration of the annual National Mom and Pop Business Owners Day!

Spring is the perfect time to stroll the charming historic streets, peruse the outdoor sidewalk sale, and dine al fresco at the expansive outdoor dining areas to enjoy a meal, dessert, or beverage surrounded by blooming flowers. SHOP, DINE & STROLL is a fun way to enjoy nice weather, special sales and promotions, and update your wardrobe and home for spring. There will also be a special LIVE MUSIC performance!

Click here for more information about SHOP, DINE & STROLL on your Downtown Winter Garden website.


The retail shops will display special sales and spring merchandise on the sidewalks. It is the perfect time to update your wardrobe and accessories for the new season, as well as to refresh the décor of your home or grab some of your favorite gourmet foods to enjoy with family and friends. Be sure to pop inside the shops for additional savings, promotions, and expanded seasonal merchandise. Click here for a list of Downtown retail shops.


Take a shopping break to enjoy freshly prepared menu items at Downtown’s one-of-a-kind eateries, and grab a seat at one of the many outdoor umbrella tables that line the historic streets to enjoy a side of Florida sunshine. Click here for a list of Downtown restaurants, cafes, and bakeries.


Stroll the brick-lined streets of historic downtown surrounded by small town charm, beautiful sights, and blooming spring flowers. Stroll in and out of the unique shops to seek one-of-a-kind finds.


Music will fill the air as you Shop, Dine & Stroll when a special live music performance by Breezeway Trio takes center stage from 4:00 pm to 7:00 pm. Grab a nearby swing, bench or outdoor table, or bring your own chair for a front row seat. Don't get too comfortable because the band's jazz tunes will have you on your feet dancing!

Breezeway Trio Live Music Performance, 4:00 - 7:00 pm

Centennial Plaza Gazebo, Historic Downtown

Shop, Dine & Stroll will be held rain or shine. Operating hours, sales, and special offers vary per merchant. Participation is at the discretion of the individual retail establishments.


Convenient parking is always free throughout Downtown Winter Garden, including at its three-level parking garage (160 S. Boyd St.) and the 117-space parking lot (37 N. Boyd St.).


Shop, Dine & Stroll is held in celebration of NATIONAL MOM AND POP BUSINESS OWNERS DAY, an annual holiday to honor small

businesses. Independent, locally owned businesses are a vital part of the United States economy and the backbone of a local

community. For every $100 spent at a locally owned business, $68 will remain in the local community, versus only $43 when shopping

at national chains, according to Independent We Stand.


Show support for ALL Mom & Pop Businesses Citywide, on this weekend and always, to help preserve what makes Winter Garden so unique.

WARNING of Fraudulent Online Solicitation: Please note that the City of Winter Garden is NOT soliciting outside vendors for this event. If you receive correspondence by either a third-party company or the likeness of the City of Winter Garden via email or social media about vending at a city event, it is fraudulent solicitation and do NOT engage in providing information or any form of payment.