The Chester Valley Rail Trail enjoys a rich history closely connected to a number of American Revolutionary War parks and monuments.

The trail runs through Battle of the Clouds Park, a site known for a battle between the armies of General Washington and General Cornwallis in September 1777 in which torrential downpour spoiled the colonial troops' black powder and forced them to retreat prior to fully engaging the British.

A 2-mile (3.2 km) remnant of the branch (from Bridgeport to King of Prussia) survived until May 2011 when short line operator East Penn Railroad abandoned it; this stretch will be incorporated into Phase 2.

Authorities from Chester and Montgomery counties, in conjunction with the Pennsylvania Department of Transportation (PennDOT) looked to convert the road bed into a walking trail.

The trail's unpaved section near the Great Valley Corporate Center is crushed stone.