Evolution of Rye’s Major Roads and Rails

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Published June 26, 2019 6:41 PM
3 min read



                                           New England Thruway construction at Rye train station looking south on Purchase Street


A Little Local History

Evolution of Rye’s Major Roads and Rails

By Paul Hicks


Baird’s History of Rye describes the principal colonial roads that ran through Rye:

“The old Westchester Path was originally an Indian trail, that led from Manhattan island to a ‘wading place’ not far from the mouth of Byram River, and thence through the present town of Greenwich, perhaps to Stamford and beyond. It was used by the Dutch and English, from the very first occupation of the country; and long before any towns or plantations appeared along its course, it formed a line of travel between New York and New England…

The roads here provided for were for the most part neighborhood roads simply…But the convenience of every town would require that there should be at least a road to the nearest settlement. This, at Rye, was the road to Greenwich or Stamford, which …We suppose this to be identical with our present post road, leading from Mamaroneck River to Byram River, in the same general course as now. That portion of it which passes through the village of Rye along the bank of Blind Brook, must have been opened before the year 1676.”

For most of the next two centuries, these were the main routes of land travel and transportation, connecting Rye with other communities, both near and far. Then in 1849, the newly-formed New York and New Haven Railroad (NH) reached Rye. Soon after, its steam-powered trains were running frequently between New Haven and the Bronx, where they connected with the New York and Harlem Railroad, leasing its tracks into New York City.

In 1872 the NH was merged into the New York, New Haven and Hartford Railroad. The “New Haven,” as the larger company was generally known, grew rapidly, largely through mergers and acquisitions. By the turn of the century it had absorbed more than 25 other lines.

In 1902, a group of investors revived a long-defunct company, the New York, Westchester & Boston Railroad, known to its riders as “the Westchester.” It was an electric commuter railroad from 1912 to 1937, which ran from the South Bronx to Mount Vernon with branches north to White Plains and east to Port Chester.

The line was completed as far as Larchmont in 1921, Mamaroneck in 1926, Harrison in 1927, Rye in 1928, and Port Chester in December 1929. The rise of the automobile, however, denied railroads the revenue benefits from the growth of the suburbs to whose growth they had contributed. The “Westchester” line closed in 1937.

The Rye station became part of the Penn Central Railroad in 1969, but due to the railroad’s financial difficulties throughout the 1970s, it was forced to turn over its commuter service to the Metropolitan Transportation Authority. For many years, Rye was also the eastern Westchester County station for Amtrak, but that stop was moved to New Rochelle in 1987.

Robert Moses first recommended the construction of what became the New England Thruway in 1940. Major work on the highway commenced in 1956 and lasted until 1961. The New England Thruway (I-95) was made a part of the Thruway toll system, but, ironically, the fifteen-mile, six-lane highway does not actually cross any part of New England, as it ends at the Port Chester/Greenwich border.

Plans for a limited-access road to cross Westchester County east to west date back to the 1920s and became more needed after post-World War II traffic increases. When the Tappan Zee Bridge was proposed around 1950, the Cross-Westchester Expressway was becoming a more realistic idea. Design and construction of the freeway, which began in 1956, was officially designated as I-487 when it opened in late 1960. Later, it was re-designated as I-287 to make it a part of the beltway around New York City.

There were plans for I-287 cross Long Island Sound via the proposed Oyster Bay–Rye Bridge. Fortunately, the plans for the bridge, and the I-287 extension onto Long Island, were dropped in 1973 by Governor Nelson Rockefeller as a result of community opposition and environmental concerns.

In August, 2018, the New York State Thruway Authority announced the start of construction on a section of the New England Thruway (I-95) known as the “Last Mile.” Improvements are being made along the final one mile stretch from exit 22 to the Connecticut state line. Work is expected to be completed in 2021.

The announcement stated that more than 140,000 motorists travel the “Last Mile” every day, which is likely to be more than all the people who traveled between Rye and Greenwich in a year even a century ago

New England Thruway construction at Rye train station looking south on Purchase Street


Photo courtesy of the Westchester Historical Society

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