Construction was initially set to begin in July 2007.[3] It was built in five phases. The final stage from Morgan lake in the Town of Poughkeepsie to the Walkway over the Hudson was completed in July 2013.[4]
Conrail's Maybrook Line was double tracked, allowing for a simultaneous paved and packed dirt trail.
The railroad line was built in 1892 by the Central New England Railway; it was severed by a fire on the Poughkeepsie Bridge on May 8, 1974. Dutchess County originally purchased the Maybrook Line to build a limited access highway to Interstate 84 but did not want to pay the monetary and environmental costs of connecting from Hopewell Junction to I-84. At the Hopewell Junction terminus of the train, the Maybrook Trailway, another nearby trail, was later completed and connected in 2020 as part of the Empire State Trail project.