By the 1980s, the corridor's then-owner, Conrail, had routed all rail traffic in the region north through Selkirk Yard and was eager to relieve itself of the bridge and adjoining rights-of-way.

During the 1990s, a broadband utility seeking to lay fiber optic cable paid the town to pass through the former corridor.

As it passes through Highland, the trail is carried by several bridges, connects to four parking areas, and traverses a wetlands complex.

[6] After Penn Central went bankrupt, Conrail assumed control of the corridor, but opposed renovating it due to budgetary concerns.

[7] Rail traffic up to the bridge continued until March 1982, when Conrail received permission from the Interstate Commerce Commission to completely cease using the corridor; the tracks were removed the following year.

[8] Donald L. Pevsner, a transportation lawyer from Florida, secured a first-refusal option for purchasing the corridor to create restaurants and tourist attractions, but allowed it to expire on November 1, 1984, because he could not secure financial backing;[9] he claims that Conrail expressed a desire to sell the corridor, at that point a potential liability, to the "first warm body" that would buy it.

[10] Conrail immediately sold the Poughkeepsie Bridge and adjoining rights-of-way on November 2, 1984, for one dollar to Gordon Schreiber Miller, a convicted bank fraudster[11][12] who "seemed uncertain what he wished to do" with the corridor.

In 1991, Ulster County seized the right-of-way west of the Poughkeepsie Bridge and gave over 5 miles (8.0 km) of the abandoned corridor to the town of Lloyd.

[17] Initially 2.5 to 3 miles (4.0 to 4.8 km) long,[16][17] it stretched from Riverside Road in the west to Vineyard Avenue in the east; the removal of an overpass on Vineyard Avenue, as well as a blockage under a bridge on U.S. Route 9W, prevented the trail from continuing east to the Poughkeepsie Bridge.

[18] Additional funding for the eastern extension was provided in November 2006, when the state granted $1.5 million to construct a bridge and a tunnel, and to complete the path.

[24] Costantino subsequently became town supervisor,[25] and the caboose had its paint replaced and was repaired at a total cost of $4,500.

[23] Lloyd's police department became the first in the county to purchase a Segway,[27] in 2007,[28] for the express purpose of patrolling the rail trail.

[31] The Rail Trail Association also received a $1,500 grant from a public-benefit corporation, the Hudson River Valley Greenway, to print brochures.

The only remaining obstruction was the placement of a bridge[25] carrying Mile Hill Road over the trail,[16] which was expected to be completed in August.

[23] Black Creek is one of the two "principal streams" to run through Lloyd; it bisects the town as it flows north and pools in a pond.

[47] The trail continues an additional 0.5-mile (0.80 km) past the beginning of the complex to Tony Williams Park.

[23] The trail is 12 feet (3.7 m) wide and 4 miles (6.4 km) long; it is paved with asphalt and suitable for hiking, bicycling, horseback riding, roller blading, and cross country skiing.