A library patron, Al Brecken, recently brought in some photographs he took of a remnant railroad bed he found in backcountry. It seems that around 1868 work was begun on the New York, Housatonic and Nothern Railroad, which was to run from White Plains across the northwest corner of Greenwich through Danbury to Brookfield. Silas D. Mead, who owned a 336-acre estate along the proposed route, even had his own men work on the roadbed. Local people were hired to haul dirt and lay track. Mr. Brecken also came across some gold stock certificates which were issued to finance the project. Unfortunately, the railroad never materialized. The owners defaulted (never paid) and the railroad was never finished. All that remains is the railroad bed and the gold certificates.
In researching the history of this railroad, I discovered that this wasn't the only rail line planned to cut through Greenwich. A Ridgefield and Port Chester Railroad (R&PCRR) was to be built from Port Chester through the heart of Greenwich. It would follow the main line in Byram, follow Water Street to the Post Road, curve northeast toward North Street, then head toward the northeast corner of town. Once again, the owners ran out of money, and could not complete the project! In 1906, the New York, New Haven and Hartford Railroad (NY, NH & HRR) acquired the Ridgefield line, but released the railroad when its charter expired in 1907.
In July 1906 the NY, NH & HRR proposed building two "relief branches" from Bruce Park in Cos Cob - one for passengers and one for freight. The routes would be double-tracked and electrically powered. One would parallel North Street and the other would run northeast between Indian Harbor and Cos Cob Harbor, cutting right through the present day Milbrook Country Club. The new lines were to be called the Greenwich-Danbury Route 1 and Route 2, respectively. At the end of 1906 it was decided that there would be only one line running northeast through Ten Acres - once a meadow owned by Theodore Mead at the foot of Put's Hill, where the high school is today. A Mrs. Anderson, who owned property at the end of the route, objected and a new route was surveyed through E. T. Seton's property. In January 1907, a special town meeting was called to discuss the issue. Seton was opposed to Route 2, which he felt would ruin his property. Others were opposed to Route 1 and still others objected to any route! Nonetheless, the first route was selected by a unanimous vote. After the meeting, many opponents petitioned the railroad and officials gave up on building the line. Instead, a line was eventually built from the station in Stamford, thorough Glenbrook and Springdale to New Canaan. I've heard it referred to as the New Canaan Line.
Not very often mentioned was the tentative plan to run a spur line parallel to King Street up to the proposed United Nations Headquarters in 1946. The compound was to be built where American Can used to have its headquarters. Residents opposed the site, citing the stress it would cause on utilities such as water, electricty, sewage, etc. Also, residents were afraid that the pristine rural landscape would turn into an urban setting. A train line would no doubt contribute to this problem. It is no surprise that this plan was abandoned, and the United Nations Headquarters was built on the East River in New York City.
At one time, railroads were the most used form of transportation for people and goods. Many people made fortunes investing in railroads. If any or all of these proposed railroads had been built, many of the beautiful estates in back country Greenwich might not exist today. No doubt small villages with general stores and post offices would have sprung up at various locations along the routes. Greenwich might have evolved into an urban environment, much like Port Chester or Yonkers.
The Golden Age of Railroads began to fade by the mid-1950s as over-the-road (truck) transportation spread. Trucks offered flexibility in terms of schedules and mobility. If the railroads had been built in Greenwich, the town could have ended up with many more abandoned railroad beds and deserted back country villages.