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5 on this page| № | Name | Category | Address | Record |
|---|---|---|---|---|
| 01 | Kneaded Baking Co Artisan bakery and cafe known for scratch-made pastries and desserts, run as a mother-daughter business. | Bakery | 22675 Washington StLeonardtown, MDLeonardtown Historic District | Listed · independent · address on record |
| 02 | Everyday Saint Brewhouse Nano-brewery and taproom in historic downtown Leonardtown, the only brewery taproom in St. Mary's County. | Brewery | 22760 Washington StLeonardtown, MDLeonardtown Historic District | Listed · independent · address on record |
| 03 | Social Coffeehouse & Cocktail Bar Downtown coffeehouse by day that turns into a 1930s-themed speakeasy cocktail bar by night. | Coffee Shop | 41655 Fenwick StLeonardtown, MDLeonardtown Historic District | Listed · independent · address on record |
| 04 | Shepherd's Old Field Market A converted former lumber yard now housing local shops, a beer garden, and a coffee shop/deli, a community gathering hub. | Market | 22725 Duke StLeonardtown, MDLeonardtown Historic District | Listed · independent · address on record |
| 05 | The Front Porch Casual Southern-coastal restaurant known for its crab cakes, in a cozy downtown space. | Restaurant | 22770 Washington StLeonardtown, MDLeonardtown Historic District | Listed · independent · address on record |