On land owned by him along the old military road Jesse Tomlinson erected a tavern. When the Cumberland Road was built, his first tavern was deserted and a new one built near the old site. Another tavern, erected by one Fenniken, stood on both the line of the military road and the Cumberland Road, two miles west of Smithfield ("Big Crossings") where the two courses were identical.
The first taverns erected upon the road which followed the portage path from Uniontown to Brownsville were Collin's Log Tavern and Rollin's Tavern, erected in Uniontown in 1781 and 1783, respectively. These taverns offered primitive forms of hospitality to the growing stream of sojourners over the rough mountain path to the Youghiogheny at Brownsville, where boats could be taken for the growing metropolis of Pittsburg. Another tavern in the West was located on this road ten miles west of Uniontown. As the old century neared its close a score of taverns sprang up on the road from Uniontown to Brownsville and on the road from Brownsville to Wheeling. At least three old taverns
