Westchester County Parks constructed the trailway in segments beginning in 1990 and completed it on October 31, 2017.

Much of the trail is in the Saw Mill River floodplain, although the southern portion runs along Tibbetts Brook.

[citation needed] The Trailway has become a bicycle commuter route for Westchester residents traveling to jobs in business centers in Elmsford, Getty Square in Yonkers, the Bronx, and Manhattan.

[9] The South County Trailway is also a section of the Empire State Trail, a route that leads north from New York City to Albany and thence either to the Canadian border or to Buffalo.

[10] A controversy developed in 2013 with the announcement that Westchester County planned to put sponsorship signage along the trail.