On one of the lots, John Hopkins established an ‘ordinary’ that later became a boarding house for immigrant Irish laborers. On another lot was a tavern and stage coach office to serve people traveling from Culpeper Court House to New Market, Virginia. On other lots were a cobbler’s shop, stores, and individual homes. In the early 1800s John Kiger built Conestoga wagons in the area. The post office was established in the village in 1840. In the 1850s several turnpikes were constructed that accessed Sperryville: Thornton’s Gap from Culpeper to Sperryville, Newmarket & Sperryville, and Sperryville-Rappahannock from Sperryville east to the Rappahannock River. A tannery and worker’s homes were constructed in the late 1860s by the Smoot family.  Four churches were established in the area by 1880, as well as a woolen mill, seven distillers, two hotels, four general stores, and one saloon.  There were also ten corn and flour mills nearby. An apple processing facility was built in 1918 to serve the many local apple orchardists. Sperryville high school was constructed adjacent to the town. In the 1930s, a Civilian Conservation Corps camp located at Beech Spring west of the village provided farmers with a nearby market for produce, meat, milk, and eggs to feed the corpsmen housed there.  The Sperryville apple packing and juice plant was created on the site of the former Smoot tannery.