Roberts Inn was one of several 19th-century taverns that stood along Frederick Turnpike, also known as MD 144, a road that had reached this area by 1808 and connected Baltimore with Frederick and western Maryland. The turnpike quickly became popular with drovers and passenger coach services. Thomas Cook, founder of Cooksville, built the inn, and by 1820 Zachariah Roberts had rented the house from Cook and opened a tavern there. He lived there with his family and at least two enslaved African Americans. Cows were raised to supply the inn with milk, butter, and beef, while hay was grown to feed guests' animals. By the mid-19th century, the turnpike faced direct competition from the railroads, which hauled goods faster and more cheaply, and the tavern soon closed and returned to use as a home and working farm. Tradition holds that Lafayette ate breakfast there during his 1824 tour of America. An archaeological dig at the site uncovered a dense trash pit in the front yard with many butchered animal bones, mostly from the upper legs of cows, suggesting that guests ate beef roasts and stews rather than steaks or ribs. Archaeologists also found dining-related artifacts including a wine glass stem and a plate, and an 1880 map showed the inn and other Cooksville businesses such as stores, a post office, physicians, a blacksmith shop, and numerous residences.