 US 11 is the descendent of a trail blazed from Pennsylvania following the establishment of Evan Watkins 's ferry across the Potomac River at the mouth of Conococheague Creek in 1744 . This trail became part of the Great Wagon Road from Philadelphia south through the Great Appalachian Valley to Virginia and North Carolina . In the center of the Hagerstown Valley along the trail , German immigrant Jonathan Hager laid out his namesake town in 1762 . In the 19th century , the Hagerstown and Middleburg Turnpike was constructed between Hagerstown and Middleburg , a settlement on the Pennsylvania side of the state line . In <unk> the Williamsport and Hagerstown Turnpike was constructed between the town that sprung up at the Potomac River crossing and the county seat of Washington County . Starting in 1896 , the Hagerstown Railway Company of Washington County operated an interurban between Williamsport and Hagerstown adjacent to the turnpike . The streetcar suburb of Halfway developed along the turnpike and trolley line at the midpoint between the two municipalities . 
