The Poughkeepsie and Eastern Railroad was chartered April 13, 1866 to be built from Poughkeepsie on the Hudson River northeast to Boston Corners in Ancram, Columbia County, NY, and then southeast to the Connecticut state line, where it would connect with the Connecticut Western Railroad, which would continue east to Hartford, Connecticut. The line opened on January 24, 1871 and ran from Poughkeepsie to Stissing. At Stissing the P&E had trackage rights to use that portion of the Dutchess and Columbia Railroad line that ran from Stissing to Pine Plains. On October 1, 1872 the remainder of the P&E line was opened from Pine Plains to the state line. The P&E's main yard and engine facilities were at the Smith Street Yard in Poughkeepsie, where there was a passenger station, a freight house, turntable and engine house. The localtrolley line on Smith St. also served the station. From the Poughkeepsie yard P&E trains traveled east through Pleasant Valley, Salt Point, Clinton Corners, Stanfordville, Stissing, Pine Plains, Boston Corners and State Line near Millerton. It was anticipated that in addition to passenger service, the railroad would make money hauling iron ore from the ore beds of Columbia County, and milk from local dairy farms; however, revenues were not as great as expected.
Receivership
On June 24, 1874 the company went into receivership. It was sold in April 1875 and reorganized May 15 as the Poughkeepsie, Hartford and Boston Railroad. It again went bankrupt and on January 26, 1884 the Hartford and Connecticut Western Railroad bought the section southeast of Boston Corners, to which they already had track rights. The rest was sold in late 1886 and on January 22, 1887 it was reorganized as the New York and Massachusetts Railway. Profit was still hard to come by, and it entered receivership for a third time in February 1893. It was sold under foreclosureMarch 2 and reorganized April 13 once under the name, the Poughkeepsie and Eastern Railway Company. Yet again, on June 17, 1898, the company went into receivership. On July 12, 1904 P&E had a wreck at Salt Point when a passenger train was mistakenly switched to a siding where a freight train was waiting. The conductor on the passenger train was injured. In 1907 the New York, New Haven and Hartford Railroad bought it and on June 25 merged it into the Central New England Railway. The CNE had been forced to build the parallel Poughkeepsie and Connecticut Railroad in the late 1880s due to the Poughkeepsie and Eastern's refusal to sell. In 1910 the P&C was abandoned between Salt Point and Pine Plains, with trains rerouted over the P&E. With the 1925 abandonment of the P&E from Ancram Lead Mines northeast to Boston Corners, the P&C served as the sole route east of Pine Plains. Abandonment came in 1938 to the rest of the P&E.
