Nestled in the Berkshire Hills of western Massachusetts and Connecticut is a hidden gem of railroading. Housatonic Railroad is a 120-mile short line, headquartered in Canaan, Conn., a small town 47 rail miles north of Danbury, Conn., and 37 rail miles south of Pittsfield, Mass. Canaan is the base of operations, home to the locomotive shops, dispatcher, clerk, main office, and maintainers, and is where most of the train crews report for duty.
To understand how the present-day Housatonic gained its identity, you need to explore its roots. The original Housatonic Railroad was chartered in 1836 to build from Bridgeport, Conn., on Long Island Sound, north to the Massachusetts state line. From there, Berkshire Railroad was chartered the following year to build to West Stockbridge, Mass. West Stockbridge Railroad was incorporated to build to the New York state line, and continue as Hudson & Berkshire Railroad to reach the Hudson River.
The final portion of the route was Stockbridge & Pittsfield Railroad, incorporated in 1847 to connect its namesake cities. All of the segments were unified under Housatonic Railroad in 1850. A short segment of the grandly named New York, Housatonic & Northern was acquired in 1871, and Danbury & Norwalk Railroad joined the fold in 1881.
ABOVE: Canaan is the heart of Housatonic, with the crew office, shops, and maintainers located at milepost 48. A southbound train passes the enginehouse on February 10, 2019. —Dave Jacobs photo
New York, New Haven & Hartford acquired Housatonic in 1892, and operated the route right up to its forced takeover by Penn Central in 1969. The railroad was a popular way to travel for weekend vacationers destined for the Berkshire Mountains, with service offered from New York to Danbury and Pittsfield. When Amtrak was formed in 1971 to take over the nation’s long-distance passenger trains, the Pittsfield train was not included, and made its last run on April 30 that year. By 1974, the middle section between Canaan and New Milford, with no active industries, was abandoned. However, by nothing short of a miracle, the state of Connecticut stepped in to purchase that section and banked it for future rail use.
When Conrail assumed operation of the former Penn Central lines in 1976, freight service was operated between Pittsfield and Canaan, and from Danbury to New Milford. Conrail eventually gave up on the northern half — the “Canaan Secondary” — and sold it to Boston & Maine in April 1982. In 1984, B&M was purchased by Guilford Transportation Industries, but sporadic strikes and other issues saw service reduced to once a week.
The “new” Housatonic Railroad Company (HRRC) was chartered in July 1984 by entrepreneur John Hanlon, who began running passenger excursions from Canaan to Cornwall Bridge, Conn., a distance of approximately 15 miles. Enjoying modest success, the remainder of the line was reopened in 1989 all the way to New Milford, where HRRC could interchange with Conrail. It was then Housatonic began servicing its first freight customers in Canaan.
ABOVE: Housatonic Railroad Train NX-12 passes through Risings, Mass., in September 2017. —David T. Magill photo
Hanlon continued to invest in the railroad by purchasing the northern portion of the Berkshire Line between the state line and Pittsfield from Guilford in 1991, establishing another interchange with Conrail at the northern end. The three-mile segment from the state line to Canaan was sold to the state and then leased to Housatonic, creating one continuous operation from Pittsfield to New Milford.
The railroad grew once again with the acquisition of Conrail’s Danbury Cluster on December 30, 1992, creating Housatonic subsidiary Danbury Terminal. This included the New Milford Industrial Track from Berkshire Junction (just north of Danbury) to New Milford, and the Danbury Secondary (a portion of the former New Haven Maybrook Line) from Derby Junction through Danbury and Beacon, N.Y. The deal also included trackage rights to serve the remaining freight customers on Metro-North’s Harlem Line from North White Plains to the end of track at Wassaic, connecting to the former New Haven track at Dykemans, N.Y. Passenger excursions ended in 1993 as the railroad had nearly doubled in size overnight and regular freight service became the priority.
By the time Housatonic took over in 1993, the only remaining freight customers on the upper Harlem Line were King Lumber in Golden’s Bridge and a Grand Union warehouse in Mount Kisco. The warehouse was closed by 1995 when the supermarket chain went bankrupt, and King Lumber switched to truck delivery soon after HRRC began regular operations. Despite a lack of customers, freight rights remain active…