LEONARDTOWN, Md. — A fresh wave of commercial activity is reshaping Leonardtown’s business landscape in St. Mary’s County, with new restaurants opening, popular eateries relocating, professional services arriving, and retail concepts launching in quick succession.
The Leonardtown Business Association compiled the developments in a February 2026 update, emphasizing how these changes reflect private investment and adaptation in the county seat’s downtown and surrounding commercial corridors.
Among the most immediate additions is Domoishi, which began serving customers in the former SIP space adjacent to Dunkin’ Donuts on Washington Street. The restaurant introduces a menu centered on customizable poké bowls, ramen dishes, chicken wings, and boba beverages, targeting both quick lunches and casual dining in a busy section of town.
Nearby on Fenwick Street, Smash House held a ribbon-cutting event to mark its official opening at a new, expanded location. The relocation from its previous spot allows the smash-burger specialist to accommodate more patrons and strengthen its position as a go-to casual dining option in Leonardtown.
The original Smash House space inside Shepherds Old Field Market will soon transition to Bowl 29. The incoming business intends to preserve the market’s community-oriented atmosphere while adding its own menu selections, continuing the site’s role as a local staple for groceries and prepared foods.
Professional services expanded with the opening of a First Home Mortgage branch on Courthouse Drive. The new office provides mortgage lending and home-financing expertise directly in town, serving residents navigating Southern Maryland’s active housing market.
Kneaded bakery is preparing to move into a significantly larger space within the historic Old Bell Motor Company building. The shift to the prominent downtown property will enable greater production volume, an extended lineup of pastries and treats, and improved accessibility for walk-in customers drawn to Leonardtown’s historic core.
Italian dining favorite Noli’s Italian Cucina has transferred to new owners who plan to reopen the establishment shortly. The changeover seeks to maintain the restaurant’s longstanding reputation while introducing operational updates to keep it competitive in the local food scene.
Retail diversity grows with The Vintage Collective scheduled to occupy the former Kenny’s Flowers location. The store will focus on curated vintage goods, antiques, and one-of-a-kind items, offering shoppers an alternative to standard retail in the town center.
Taken together, these transitions and launches illustrate Leonardtown’s ability to retain and attract entrepreneurs amid broader economic patterns in St. Mary’s County. The Leonardtown Business Association views the activity as a sign of sustained optimism, with businesses actively reinvesting in physical spaces and customer experience.
Additional information on these businesses and future announcements is available through VisitLeonardtownMD.com. Leonardtown’s ongoing evolution combines its preserved 19th-century architecture with contemporary commercial offerings, supporting its status as a regional draw for dining, shopping, and services in Southern Maryland.