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Shop, Dine and Stroll in Winter Garden Downtown Historic District

March 25, 2023

Shop, Dine and Stroll in Winter Garden Downtown Historic District

Outdoor Shopping & Dining Experience with LIVE MUSIC in the picturesque Winter Garden Downtown Historic District in celebration of the annual National Mom and Pop Business Owners Day!

All-Day (Open to Close)

Location: Winter Garden Downtown Historic District, 300 W. Plant St.


Shop the outdoor sale racks of the local stores; dine al fresco surrounded by blooming spring flowers, and stroll the charming historic streets of Downtown Winter Garden. An outdoor live music performance at Centennial Plaza will add to the day’s festivities. SHOP, DINE & STROLL is a fun way to enjoy the season’s pleasant weather while enjoy sale!


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.


Take a shopping break to take a seat in the expansive outdoor dining areas to enjoy a meal, dessert, or beverage encased by beauty and charm. The umbrella seating areas line the historic streets to enjoy a side of Florida sunshine with your meal.


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 the BREEZEWAY TRIO takes center stage at Centennial Plaza, 4 PM – 7 PM. Grab a nearby swing, bench or outdoor table, or bring your own chair for a front row seat.

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


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.


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.)


March 25, 2023
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Winter Garden Downtown Historic District
Winter Garden, FL 34787 United States + Google Map