Originally constructed by the Wallkill Valley Railroad to continue its rail line from New Paltz to Kingston, the bridge rises 150 ft (46 m) above Rondout Creek, spanning both Route 213 and the former Delaware and Hudson Canal.

Concern over the sturdiness of the trestle has persisted since its opening, and was a major reason Conrail closed the Wallkill Valley rail line in 1977.

After the rail line's closure, Conrail sold the bridge in 1986 for one dollar to John E. Rahl, a private area businessman, who tried unsuccessfully to operate the trestle as a bungee jumping platform in the 1990s.

[7] Though the trestle was difficult to build,[8] and viewed as weak by modern standards,[9] it was remarkable for its time,[10] and can be considered the "most awesome part" of the Wallkill Valley rail line.

[3] The bridge was opened on April 6, 1872, in a ceremony attended by 5,000 people,[11] including prominent men from across Ulster, Orange, and Dutchess counties.

[1] In 1888, the Wallkill Valley Railroad received a permit from the town of Rosendale to "construct and maintain abutments to support [the] trestle" as long as such work did not interfere with traffic along the underlying highway (present-day NY 213).

That same year, the Delaware and Hudson Canal allowed the railroad to temporarily use some of its property by the Rondout Creek to place bents for bridge repairs.

The "speed, weight, and positioning of rolling stock on the bridge" was monitored,[3] and it was repeatedly reinforced to "carry the ever heavier loads of modern railroading".

[29] By 1975, the rail line had deteriorated to the point where federal regulations allowed only 8-mile-per-hour (13 km/h) traffic over the trestle,[30] though engineers were instructed to go no faster than 5 miles per hour (8.0 km/h).

[33] Conrail sold the bridge, along with 11.5 miles (18.5 km) of the Wallkill Valley rail corridor, in 1986 to a private businessman, John E. Rahl, for one dollar.

[32] Rahl's reason for buying the rail line was originally to open a "dining car restaurant" along the corridor,[33] and to establish a tourist railroad from Kingston to the trestle.

[9] He claimed the purchase granted him the right to "restore rail service on the whole Wallkill line",[37] and also joint ownership of Conrail: an incredible assertion which did not prevail.

[32] On May 16, 1989, a storm caused such severe damage to the Binnewater station that part of it broke-off and fell into the road;[35] the building was subsequently demolished by the town of Rosendale's highway department.

The Wallkill Valley Land Trust and Open Space Conservancy offered to purchase the property, and the county authorized the sale in July 2009.

[50] The Land Trust agreed to pay all outstanding taxes before receiving full ownership and adding it to the Wallkill Valley Rail Trail.

[58] On February 17, 2011,[59] a Bergmann Associates employee used the trestle as a case study in a seminar on adaptive reuse of defunct railroad bridges.

[60] By late March, 2011, the estimated cost of renovating the trestle had risen to $1.1 million,[61] and the expected time to completion had increased to two years.

Rahl had claimed that he retained ownership of the property because only the state, and not the county, had the right to seize the trestle, which was "forever railroad under 19th century eminent domain legal doctrines – long forgotten by modern jurisprudence".