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5 on this page| № | Name | Category | Address | Record |
|---|---|---|---|---|
| 01 | The Upper Crust A longtime neighborhood bakery near Main Street known for pies, cakes, buns, and other baked goods. | Bakery | 2 N Pendleton StreetMiddleburg, VAHistoric Washington Street District | Listed · independent · address on record |
| 02 | The Artists In Middleburg A nonprofit community gallery hosting rotating monthly exhibitions by local artists and offering art classes to the Middleburg community. | Gallery | 102 W Washington StreetMiddleburg, VAHistoric Washington Street District | Listed · independent · address on record |
| 03 | Mt. Defiance Cidery and Distillery A working cidery and distillery with a Main Street tasting room pouring house-made ciders, rums, apple brandy, and Virginia's only absinthe. | Bar | 207 W Washington StreetMiddleburg, VAHistoric Washington Street District | Listed · independent · address on record |
| 04 | Cuppa Giddy Up A family-owned coffee shop operating since 2001, serving organic, fair-trade coffee and espresso with locally sourced pastries from a basement-level space just off Main Street. | Cafe | 8 E Washington StreetMiddleburg, VAHistoric Washington Street District | Listed · independent · address on record |
| 05 | Red Fox Inn & Tavern A fieldstone tavern reputedly established in 1728, considered one of the oldest continuously operated inns in the United States, serving American tavern fare in a historic setting. | Restaurant | 2 E Washington StreetMiddleburg, VAHistoric Washington Street District | Listed · independent · address on record |