The Ashokan Rail Trail is located on the north side of Ashokan Reservoir and Esopus Creek in the towns of Hurley and Olive, New York, United States. It is an 11.5-mile-long (18.5 km) pathway along the former route of the Ulster and Delaware Railroad (U&D) between West Hurley and Boiceville. It was opened partially in 2019 and fully in 2020, allowing the general public recreational access to that land for the first time in over a century, since New York City built the reservoir for its water supply system.^[1]

Prior to the construction of the rail trail the tracks, last used commercially by Conrail in 1976, were used by the Catskill Mountain Railroad (CMRR) for excursion trains along that portion of the U&D line it owned between Kingston and Phoenicia. The CMRR was never able to fully rehabilitate the tracks, and damage caused by Hurricane Irene in 2011 was beyond its ability to repair, and in 2017 Ulster County terminated the railroad's lease on section where the rail trail is now, replacing the damaged Boiceville Trestle in the process with a newer, flood-resistant structure.

Discussions continue over plans to connect the rail trail to longer regional trails in the state's Empire State Trail network. The use of the 1.7-mile (2.7 km) section of the rail line just east of the West Hurley trailhead in the towns of Woodstock and Kingston has never been designated. The CMRR has advocated for rail-with-trail on the segment and has applied for a permit to build a station complex to serve the rail trail. Local conservationists have advocated for an extension of the rail trail on that section, arguing that environmental and engineering issues make the rail-with-trail option more costly than the railroad estimates.

The rail trail officially begins at the railroad's 10th milepost (MP), marked along its route by signs every half-mile (800 m) with the number prefixed by a "K", just west of where it crosses over Basin Road near the western corner of the town of Woodstock. It is just east of the Ashokan Reservoir, part of the New York City water supply system's Catskill/Delaware watershed, and a short distance south of New York State Route 28, at 581 feet (177 m) above sea level. Within its first half-mile it crosses into the town of Hurley^[2] and runs abreast of the reservoir at Woodstock Dike, site of its eastern trailhead and parking lot in West Hurley, where views of the 13-square-mile (34 km²) reservoir and adjacent peaks of the Catskill Mountains are available.^[3]

Continuing west through the forested lands that buffer the reservoir for another half-mile, sometimes through rock cuts, the trail bends slightly towards the northwest. It reaches the longer Glenford Dike, with wider views of the reservoir and some of the Catskill High Peaks to its west. This section continues for a quarter-mile (400 m) after which the trail re-enters a narrow strip of woods between the reservoir and NY 28. A mile further, it returns to its western course, running less than a hundred feet (30 m) south of the highway, reaching 680 feet (210 m) in elevation and curving southwest after another mile.^[3][2][4]

After another four miles, the trail enters the town of Olive and reaches the site of the former Ashokan station, now another trailhead and parking lot. Some sections in the next mile are on wooden boardwalk over wetlands abutting the reservoir. Following that it crosses under Reservoir Road south of the hamlet of Shokan. Three-quarters of a mile west of that crossing, it curves northwest again and crosses Butternut Creek at Butternut Bridge near MP 18.5.^[3][5]

Over the next two miles, the trail begins curving northward and eventually runs along the bank of the reservoir, offering views to mountains like 3,090-foot (940 m) Ashokan High Point south of West Shokan across the reservoir and High Peaks Balsam Cap, Cornell, Friday, and Wittenberg mountains to the southwest. At MP 20.5, a half-mile causeway section takes the trail to the western end of the reservoir, where the upper section of Esopus Creek drains into it. The trail continues turning, going almost due north as it crosses the Esopus at the rebuilt Boiceville Trestle and ends at its western trailhead and parking lot near Boiceville, along New York State Route 28A.^[3][6]

In the middle of the 19th century, Thomas Cornell, already wealthy from the steamboats he operated along the Hudson River, saw further opportunity in developing a rail link from Kingston across the Catskills in Ulster County that would connect with other railroads in New York's interior serving the Great Lakes. In 1866 he incorporated the Rondout & Oswego Railroad, which built tracks as far west as Roxbury in Delaware County over the next six years before being reorganized as the New York, Kingston & Syracuse after going bankrupt. In 1875 it became the Ulster & Delaware Railroad (U&D) following another bankruptcy.^[7]

The U&D made the line profitable through the early 20th century. It shipped bluestone quarried in the Catskills to the river where it was shipped to New York City for use as sidewalks, dairy products from the region's farms and coal from Northeastern Pennsylvania. In return, passengers came upriver to spend their summers at the Catskill Mountain House and other popular large resorts. Ferries across the Hudson also allowed passengers from that region to take what was advertised as the only all-weather route to the Catskills. In 1900 the U&D achieved Cornell's original goal, reaching Oneonta in Otsego County, where it interlinked with the Delaware & Hudson Railroad's service along the Susquehanna River.^[7]

In 1913, over half a million passengers rode the U&D in the railroad's peak year. At the same time freight shipments were up as it brought material for the construction of the reservoir. That project would require moving the stretch of track north, to the current route of the rail trail. Several settlements were also inundated and the stations serving them moved or abandoned. This adversely affected the railroad's passenger volume, along with a trend towards shorter summer vacations and the opening of competing resorts in other mountainous areas. Freight, too, began to suffer during the 1920s as roads improved and trucking became economically feasible.^[7]

By the onset of the Great Depression, the U&D was again financially strapped. Its directors approached the dominant New York Central Railroad (NYCRR) about purchasing the U&D, the only way they saw to save service. Initially rebuffed, they achieved their goal when the Interstate Commerce Commission, the national rail regulator at the time, made a consolidation of NYCRR subsidiaries in the Midwest contingent on the larger railroad also acquiring the U&D. The NYCRR immediately downgraded speeds on the line, now its Catskill Mountain Branch, and planned to eliminate passenger service. Due to World War II it did not do so until 1954.^[7]

In the late 1960s the NYCRR, facing financial difficulties itself, merged with its archrival the Pennsylvania Railroad to become the Penn Central. In 1970 the merged railroad itself went bankrupt. Such freight operations as remained on the Catskill Mountain Branch were taken over by Conrail, and ended in 1976.^[7]

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