When traveling to Annapolis from his land in Frederick County (now Carroll County) John Reister must have noted that the point where the Pipe Creek Road (now Westminster Pike) joined with the older road to Pennsylvania was only sixteen miles from Baltimore Town. This would provide an ideal site for a settlement, and the fork would be an excellent location for an inn. While in Annapolis he learned about a twenty acre tract of unpatented land half a mile south of the junction of the roads. It was located just south of an Indian trail leading to the Patapsco River now known as Cockeys Mill Road.

A tavern, which provided lodging as well as food or drink, was constructed as soon as possible. Acquisition of property gave John Reister a stretch of land extending along both sides of the Conewago Road almost five eighths of a mile. As early as 1787 the name Reister's Town had been acknowledged by the Electors of Baltimore County. The first businesses catered to travelers - taverns, a store, smithshops, saddleries, and a tannery - they were soon followed by other types of commercial establishments. With the acquisition of more land the whole area north and south of the Reister land, became known as Reisterstown. Real Estate Agents in Reisterstown, MD.