Throughout Lancaster City's history, king Street has been a major throughfare between Philadelphia and points west. In 1733 work commenced on the King's Highway, now Route 340. This highway began at the square extended eastward on King Street and continued on to Philadelphia. Although the highway improved travel between Lancaster and Philadelphia, the dirt roadbed became impassable in inclement weather. In 1792 the State chartered the Philadelphia-Lancaster Turnpike Company which built the Philadelphia-Lancaster Turnpike, a part of the present-day U.S.30 and the first turnpike in the United States. The new route was constructed with a hard, macadam surface, making it passable year round.
Unfortunately, King Street itself was not surfaced, and continued to be dusty in dry weather and a sea of mud in wet weather. To avoid taxing citizens for paving the street, Lancaster received permission from the State Legislature to hold a lottery to raise $20,000. The drawing took place on May 1, 1802: First prize was $1,000, with second prize being $500; more than four thousand other prizes were awarded. On May 28th, paving began from the Conestoga River extending westward to the square.
In order to accommodate travellers, stagecoaches left Lancaster for points east and west. in the mid-eighteenth century, a traveller going to Philadelphia would catch Matthias Slough's dispatch stage line at the White Swan Hotel at 5:00 a.m. and would arrive in Philadelphia that evening.