Dutchess and Columbia Railroad

Newburgh, Dutchess and Connecticut Railroad

The company headquarters as seen in 2012
Locale	Dutchess County, NY
Dates of operation	1869–1905
Track gauge	4 ft 8 1⁄2 in (1,435 mm) standard gauge
Headquarters	Matteawan, New York

Affectionately known as "The Never Did and Couldn't", the Newburgh, Dutchess and Connecticut Railroad, began as the Dutchess and Columbia Railroad, a link in the New York, New Haven and Hartford Railroad system in New York state.

The Dutchess and Columbia Railroad was chartered September 4, 1866. It was to run from Fishkill northeast and north to meet the New York and Harlem Railroad at Craryville. Millbrook resident, George H. Brown, was elected president. The road was promoted largely by New York bankers who had financial interests in the town of Washington. Several Dutchess County towns along the proposed route bonded themselves to aid in the construction of the road. Hesitation on the part of Columbia County townships to do likewise, together with the influence of some politicians in the northern section of Dutchess County, caused the promoters change the route to turn east at Pine Plains, going over the mountains to Millerton by way of Bethel, Shekomeko and Winchells. It was also extended to State Line to connect with the Connecticut Western.

Construction began in 1868, and teams of horses pulled wagon loads of rails to be distributed along the right of way from Little Plum Point (Dutchess Junction) through Matteawan, Glenham, Fishkill and Brinckerhoff to near Old Hopewell. Bridges were built over Fishkill Creek and Sprout Creek. After this section was in place more rails would be hauled by trains to complete the line. The line reached north to Pine Plains by July 1, 1869. Construction reached Millerton in the northeast corner of the county in November 1871.

A short four-mile connecting Railroad called the Clove Branch was chartered in 1868 and opened in 1869. The CB connected with the D&C near Old Hopewell, and its main purpose was to haul iron ore out of the mine at Sylvan Lake. Later the CB was extended another four miles and ran passenger and freight service to a few customers and an iron furnace in Clove Valley. The president was the same George H. Brown who was President of the D&C RR. Operations were suspended in 1897 and it was abandoned in 1898.

The Boston, Hartford and Erie Railroad was formed from three separate companies:

In 1849, the two Connecticut companies merged to form the Hartford, Providence and Fishkill Railroad, with a modified charter to continue past Brewster to Fishkill, New York on the Hudson River. In 1851 the Rhode Island company was merged into it. Later that year the first section opened, from Hartford east to Willimantic. Extensions opened east to Providence in 1854 and west to Waterbury in 1855. The HP&F went bankrupt on January 1, 1858, and was run by the trustees until 1863, when it was leased by the newly formed Boston, Hartford and Erie Railroad. In May 1863, the Boston, Hartford and Erie Railroad was chartered to take over operations of the failed lines and continue the line west to Fishkill, New York, with a car float from there to the Erie Railroad at Newburgh. On December 1865 a number of Erie Railway men were elected to the BH&E board, placing it under partial control of the Erie.