The Westchester Northern Railroad project was supposed to extend the New York, Westchester & Boston Railway from White Plains through to Brewster and Danbury. After some false starts, the project was officially cancelled in 1925 and the funds diverted to construction of the Port Chester extension. Early reports of construction activity refer to the line as the “Westchester & Northern Railroad,” but all accounts point to the legal name of the entity as the “Westchester Northern Railroad.”
The first public mention of the Westchester Northern project comes in February 1910, with an incorporation announcement in the New York Times:
New Westchester Road Incorporates
ALBANY, Feb. 8 — The Westchester Northern Railroad Company of White Plains was incorporated today with a captial of $1 million to operate a steam or electric railroad forty-five miles long, of which thirty-five miles is to be in New York and ten miles in Connecticut. The main line is to be operated from the New York, Westchester & Boston Railway at White Plains to the line of the New York, New Haven & Hartford Railroad at Danbury, Conn. There will be a branch line fourteen miles long from Pound Ridge, Westchester County to the New York, New Haven & Hartford line in Putnam County. The Directors are L.S. Miller, W.A. Cokeley, New York City; Allan Wardwell, Lawrence; R.P. Buell, Bayside; Robert T. Bird, Hartford; James L. Crider, Mount Vernon; John C. Gleason, New Rochelle; Charles L. Nagle, Bayside; and James J. Dwyer, Brooklyn.
—New York Times, February 9, 1910
An excerpt from a 1910 New York Times article describes the finances and proposed route of the Westchester Northern Railroad:
Stations on Newest Railway – Westchester & Boston Line Lets Contracts for Nine
…At White Plains the New York, Westchester & Boston Road connects with the Westchester & Northern Railroad at Westchester Avenue. While the two companies are now distinct and run separately in every particular, they are working together and in perfect accord. …Operations on the Westchester & Northern Road are temporarily suspended. Before the late financial disturbance President Miller was ready to award contracts calling for an expenditure of between $6 and $7 million. The Westchester & Northern Railroad is to run from White Plains to Brewsters, with a branch track at Pound Ridge running to Danbury, Conn. Above White Plains it passes through the towns of Harrison and the northwestern part of Greenwich, cutting through a corner of Connecticut; then through New Castle, Bedford, Pound Ridge, Bontonville, South Salem, and North Salem, to the terminal at Brewsters. The Danbury branch passes through Ridgefield, which will be the important station on that division.
—New York Times, July 13, 1910
Here is a 1912 New York Times article describing the financing and intent of the new construction:
New Westchester Bonds – $2 Million for Starting Railroad’s Extension to Danbury, Conn.
WHITE PLAINS, N.Y., Nov. 7 – It was announced today that the New York, Westchester & Boston Railroad had sold an additional $2 million of 4.5% bonds to be used for the construction of the new Westchester Northern Railroad Company, an extension of the Westchester & Boston system. This new road will extend from the White Plains terminal of the Westchester road northward through Westchester County to Danbury, Conn. The bonds sold will provide for about 30% of the construction money. The remainder of the road will coast $5 million and bonds will be disposed of when the money is needed. The bonds just sold bring the total outstanding of the Westchester Company to $19,300,000 under an authorized mortgage of $600,000,000. Work on the construction of thw Westchester Northern, it is understood, will be started on Monday. The completion of this new road will give the New York, New Haven & Hartford Railroad, which is the chief backer of the line, a through passenger and freight system from the coal fields by the way of the Poughkeepsie Bridge through Dutchess County, Connecticut, and Westchester County to tidewater. The New Haven company also expects to run fast Pittsfield expresses over this route, as well as freight trains from Boston. The construction of this new road has caused a boom in real estate in the eastern section of Westchester County through which it will pass.
—New York Times, November 8, 1912
The next reference to the WN we could find was a 1915 article that once again announces that construction will begin soon on the extension from White Plains:
To Extend Westchester & Northern
WHITE PLAINS, N.Y., April 29 – It was reported here today that the new Westchester & Northern Railroad Company intends to start work soon on the construction of a railroad from the Westchester Avenue terminal station of the New York, Westchester & Boston Railroad Company and that the line will be built through to Danbury, Conn. It is said that the company will spend $5 million.
—New York Times, April 30, 1915
It is not known how much construction work actually took place on the WN. The NYW&B officially cancelled the WN project in 1925, diverting the funds to construct the remainder of the Port Chester extension from Larchmont. The following is a 1927 letter from railroad president Leverett Miller in response to an inquiry from Westchester County realtors about why the project was cancelled. In essence, the concept of building new passenger rail lines had been abandoned completely.
Further Co-ordination in Westchester County
Leverett S. Miller, president of the New York, Westchester & Boston Railway, proposes to solve the transportation problem of Westchester County northward from White Plains through Brewster, N.Y., and Danbury, Conn., by the establishment of feeder lines, rather than by the extension of existing railway lines. Mr. Miller’s opinion was contained in a communication to L. Ward Prince, president of Ripley & Ripley, who had asked on behalf of Westchester realtors, that the New York, Westchester & Boston extend northward its western division all-electric commuter service now terminating at White Plains.
In his letter to Mr. Prince, Mr. Miller said: “You are familiar, I know, with the fact that this company originally contemplated the extension of its lines from White Plains to Brewster and Danbury. Within the last few years, the company was faced with the obligation of completing its routes, both from Larchmont to Port Chester, and from White Plains to Brewster and Danbury, within the time limit specified by law, or lose its franchise rights.” To accomplish this would have required the expenditure of millions of dollars. The time did not seem propitious for the extension to Brewster and Danbury, but the extension from Larchmont through Mamaroneck, Harrison and Rye to Port Chester appeared warranted. “It was for this reason that the railway sought remedial legislation to relieve it of the obligation to build to Brewster and Danbury. At present-day prices it would cost to build these latter extensions double the estimate made at the time when these lines were first considered.”
In the meantime, much of the remaining undeveloped property to the south and east of White Plains has come into the market, and the growth to the north undoubtedly now will increase. But I do not believe that it is yet of sufficient extent to warrant a rail line such as was originally contemplated. “It seems to me that the more practicable solution of the transportation problem for this section is through the use of motor vehicles co-ordinated with the existing rail lines, to be followed later by the extension of the rail lines as soon as the traffic may warrant.” You refer to present-day values of land in this section and the very large increase that would result in values if transit facilities were furnished. Transportation must, to a certain extent, be a pioneer in such development, but it cannot carry the load for too long a period.” As you say, the property owners would be well repaid if they were to underwrite the cost of such an extension, but as you also remark, they won’t; they will expect the transit lines to carry the bag. The development through motor vehicle transportation would require far less investment, and consequently the underwriting by property owners in such an undertaking might be more favorably considered by them. “The working out of these problems requires the cooperation of realtors interested in the development of the section and those connected with the transportation companies. We all have a common interest in the development of the section which it seems cannot be efficiently accomplished without such team work.”
–Electric Railway Journal, September 10, 1927