Born of civic spirit to facilitate public travel and transportation of the mails between New Haven and the Naugatuck Valley, the New Haven & Derby originally operated over a route of 13 miles. It was chartered by the state legislature in 1864 but construction work did not begin until 1867 after a survey by Colonel M.O. Davidson of New York City was completed. The first contractor, George Chapman & Co. abandoned work in 1869 for non-payment. After the charter expired, the City of New Haven funded the railroad by acquiring bonds and a new charter was approved. The N.H. & D. existed at a time when railroads were regulated by the State Railroad Commission. Interstate Commerce Commission regulation came later. State law permitted cities to invest in speculative ventures such as the N.H. & D.
The new contractor, Willis Pratt of Springfield, Ma. also quit in 1871 when the directors decided to build the line to Ansonia rather than end it at Derby. Local assorted contractors finished the line. With great fanfare, the first train full of "proper New Haven citizens" arrived in Ansonia on August 5, 1871. Rural Ansonia and Derby now had a steel highway direct to the "Elm City" of New Haven. A ballad about a fictitious Derby heroine of the time went:
"...as the train pulled out of the station, she gave forth this explanation, I'm off for New Haven, so-long, goodbye; I'm off to New Haven, I don't know why..."
In 1889 the railroad was leased to the Naugatuck Railroad which was in-turn later absorbed by the New Haven Railroad.
The railroad operated on 16.79 miles of track over its 13 route miles. Trestles carried 5, 560 feet of the line. Construction occurred before the era of earth-moving equipment utilizing animal power and human labor, (likely augmented by quantities of liquor). It was cheaper to erect wooden trestles over shallow depressions than to use fill, however the Commission pressed the railroad to use fill. The Commission complained that the railroad was slow to replace iron rail with steel rail. It was finally all-steel by 1884. Substantial stations were built in Orange, Tyler City, Derby and Ansonia, with a flag-stops at West Haven, Alling Crossing and Turkey Hill. In New Haven, the N.H. & D. used the Chapel Street Union Station owned by the New Haven Railroad and the New Haven & North Hampton Railroad. The N.H. & D. was very profitable due in-part to failure of the directors in upgrading track and eliminating trestles. In 1877 it grossed $100,000 with a net profit of $46,475. Not bad for those days!
Two major trestles included one spanning Grassy Hill Road / Weapawaug River in Orange.
It was of wood construction resting on 50-foot stone piers. All piers were removed after
the railroad closed.
In 1871 the N.H. & D. owned 3 engines, 4 passenger cars, 8 box cars and 20 gravel or coal hopper cars. By 1887 it owned 7 engines, 9 passenger cars, 53 hoppers and 16 box cars. Trains were short. A freight train may have 8 cars and a passenger train two cars. Two round-trips a day served Orange. An 1883 timetable shows a travel time of 26 - minutes from Orange to New Haven. Over 110,000 passengers used the railroad in 1887. It employed 48 persons. In 1888 passenger trains ran 5,693 miles and freights 4,679 miles. In 1889 40,635 tons of traffic was generated on-line and 75,305 tons received-off line. Traffic for 1889 included 17,000 tons of coal, 13,000 tons of sand and gravel, 5,572 tons of lumber and 2,184 tons of liquor! Copper and sheet-metal provided significant business. In 1889 the Housatonic Railroad leased its “New Haven and Derby Division.” In order to connect together, the N.H. & D. built to Huntington while the Housatonic also built to Huntington from Botsford Junction.
Mack Railbus passenger service ended on June 13, 1925. By 1937, the New Haven-to-Orange
section was torn-up. Service to Orange was provided from Derby Junction. The line at
that time carried cement to a mix plant used in the construction of Route 15 / Wilbur Cross
Parkway. Power was a T-2-B, 0-6-0 wheel arrangement steam switcher weighting 71 tons. The
railroad ceased operation with Derby Junction-to-Orange being torn-up on May 26, 1941.
Most of the track and infrastructure were abandoned or dismantled however some of it still
exists if you know where to look. Much of the right-of-way can still be imaged on Google
Earth, especially in Orange. The main freight yard was located at the present Yale School
of Nursing site. The level earth depression was the foundation of the yard. The right-of-way
traveled through Allingtown via a steel viaduct, under Rt. 1 via a tunnel (where the pre-fab
tool shed business stands today), and over West Haven's Campbell Avenue on a concrete trestle.
Passing through part of the present VA Hospital grounds, it then snaked into
Orange (much of the cinders / tree lined right-of-way exists); traveled along the north
border of the Orange Hills Country Club ...across Race Brook Road... and crossed Lambert Road at
Porter Lane on its way to Tyler City. One can see a culvert on the east side of Lambert
Road as you approach Porter Lane. From the northwest corner of Porter and Lambert the
railroad traveled north, crossing Tyler City Road. (If you walk along Tyler City Road
between Lambert and Orange Center Road; off to the south is an open rock cut and some
well-deteriorated ties. You will need to walk deep into the woods to find this, keeping
the pond on your right). The railroad crossed Orange Center Road along the north edge of
the shopping center. Look for the preserved Railroad Crossing Sign indicating the Orange
Center Road crossing. The line continues through the woods, crossing Ridge Road; then
Grassy Hill Road before heading to Turkey Hill. It crossed the Derby-Milford Road three
times; twice by grade and once over a trestle (whose one huge 40-foot stone abutment still
exists at the sharp curve in the road), then down the (existing) earthen ramp and finally
connecting with today's Metro North-
Connecticut Railroad Commission Annual Reports, (available at Quinnipiac Univ. Law Library).
Connecticut Railroads, Turner, Greg M. and Jacobs, Melancthon, W.
The Connecticut Historical Society, 1986
New Haven and Derby Railroad Club, New Member Packet, Trowbridge, James A.
New Haven Streetcars, The Branford Electric Railway Association, Images of Rail. Arcadia Publishing Company.
New Haven Railroad Employees Timetable
The Shoreliner, Belletekie, Robert. The New Haven Railroad Historical and Technical Association, Inc. 1981 issue, month unknown.