When the railroads were king

Clockwise from top left: The O&W Station in Uptown Kingston, torn down in 1969 (Bob Haines Collection); the U&D Railroad turntable (used to turn trains around) and roundhouse (for maintenance and storage) in Rondout (Jerry Mastropolo Collection); the train bridge over the creek and the D&H Canal under construction in Rosendale, now part of the Wallkill Valley rail-trail (D&H Canal Society).

Four railroad lines carrying both passengers and freight passed through Kingston during the industry’s heyday in the late 19th and early 20th centuries. All but the Ontario & Western (O&W) passed through Midtown’s Union Station, built in 1883 and torn down in 1967. Rail service began its decline in the 1930s due to the Depression followed by a rise in automobile use.

The Ulster & Delaware Railroad (U&D) began as the Rondout and Oswego (R&O) founded by Thomas Cornell in 1866. After a series of bankruptcies, it was reorganized as the U&D in 1875. The line extended from Kingston to Oneonta, passing through four counties: Ulster, Delaware, Schoharie, and Otsego. Passengers could transfer from steamships docked in Rondout to the train station located near today’s Hudson River Maritime Museum. 


The U&D was extended to Kingston Point when the amusement park opened in 1897. The station was situated directly across from the steamship landing so travelers could easily catch trains heading to popular resorts in the Catskill Mountains. 

Freight made up a large part of the railroad’s income, carrying industrial goods from the terminus of the D&H Canal into the mountains and returning with vegetables, fruit, and milk from Catskills farms. From 1908–1912, the railroad carried supplies for the construction of the Ashokan Reservoir, and 12.5 miles of its track were relocated after the route along the Esopus Creek was flooded to create the reservoir. After the D&H Canal closed in 1899, the vast majority of rail freight consisted of coal until the industry waned in the 1920s. 

By 1932, the struggling U&D was acquired by the New York Central Railroad, which gradually reduced trips and closed the Rondout station in 1938. Passenger service ended in 1954 and freight in 1976.  

The Catskill Mountain Railroad began operating a tourist train in 1983 that continues today along part of the line with a popular fall foliage tour and the kids’ favorite, The Polar Express. In 2019, an 11.5-mile section was converted to a well-used recreational path, the Ashokan Rail Trail, along the reservoir between West Hurley and Boiceville.

A packed platform at Union Station in Midtown Kingston during World War II. (Bob Haines Collection)

The Wallkill Valley Railroad was founded in 1866 primarily to transport agricultural goods north from Montgomery in Orange County, NY. It was designed as a six-foot gauge in order to connect with the Erie Railroad. Thomas Cornell became president in 1872, presumably to ensure its extension to Kingston, and then purchased the struggling line again in 1877. He sold it to the West Shore in 1881 at a substantial profit. 

Passenger service ceased in 1937 and freight in 1977. The route was later converted to the popular Wallkill Valley Rail Trail that includes a renovated trestle bridge in Rosendale and a nearby cafe offering snacks and live music to hikers and bikers.  

The New York, Ontario and Western Railway (O&W) began as the New York and Oswego Midland Railroad in 1868. It followed a rugged route through small inland towns between Lake Ontario and New Jersey. It went bankrupt almost immediately and was reorganized in 1880 with its new name. 

The O&W became a major tourist transport to the mountain hotels and camps in Orange, Sullivan, and Delaware counties, known as the “lower Catskills.” Freight trains transported dairy and coal. In 1902, a spur was added from Ellenville to Kingston, but never turned profitable. The railroad’s ongoing financial struggles and lumbering pace earned it the nickname ”the Old & Weary.” 

The railway’s rural routes became obsolete when coal use declined, manufacturing moved south, and populations moved to urban and suburban areas. By 1937, the line went bankrupt. Passenger service ended in 1940 and the last load of freight traveled the line in 1957. 

The New York, West Shore & Buffalo Railway Company was founded in 1881 to connect Weehawken, New Jersey with Buffalo, NY in direct competition with the New York Central & Hudson River Railroad which ran parallel across the Hudson River. It went bankrupt only a few years later and was reborn as the West Shore Railroad Company under the ownership of its former competitor. 

West Shore passengers from New York City could continue north all the way to Buffalo or transfer at Kingston’s Union Station to U&D trains that would carry them west to the Catskill Mountains.

Passenger service on the West Shore line ended in 1958. A portion of the track continues to be used for freight, now run by CSX, which stands for Chessie Seaboard X, the latter used as a symbol of consolidation.

To see sample pages and information about supporting this 450-page book featuring 850 images that will be released in December 2021, please visit:  HudsonValleyHistoryAndArt.com.

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