Long Island to Connecticut: 80 Years of Bridge and Tunnel Ambitions

The idea of connecting Long Island to Connecticut—or even Westchester and Rhode Island—has been around for over 80 years. Here’s a fascinating look at the history of the “Long Island Sound link,” a proposal that has sparked endless debate, massive studies, and plenty of drama.

Origins

  • The first proposal came in 1938, when U.S. Senator Royal Copeland suggested an 18-mile bridge from Orient Point, NY, to either Connecticut or Rhode Island.
  • Throughout the decades, there were suggestions to connect Oyster Bay to Rye, NY, and Orient Point to Watch Hill, RI.
  • The idea was significant enough to warrant its own Wikipedia page and even appeared as a plot point on the Netflix show House of Cards.

1960s: Rockefeller’s Push

  • In 1965, Robert Moses proposed a $100 million bridge from Rye to Oyster Bay.
  • By 1967, Governor Nelson Rockefeller signed legislation authorizing the Oyster Bay-Rye Bridge and proposed another 14.6-mile bridge from Port Jefferson to Bridgeport, CT.
  • Despite Rockefeller’s enthusiasm, fierce opposition arose from environmental groups, local governments, and Congress.
  • A 1973 New York Times article detailed widespread concerns: dwindling wetlands, increased traffic, loss of green spaces, and threats to the Sound’s recreational value.

Port Jefferson to Bridgeport (1968)

  • A study proposed a 14.6-mile bridge costing $368.3 million, with a new expressway linking Port Jefferson to Nicolls Road in Centereach.
  • The NYSDOT’s 1971 study considered five alternative crossings but ultimately favored a Nassau-to-Westchester span.

Shoreham to New Haven (1970s)

  • In the late 1970s, proposals shifted east to Shoreham, envisioning a 19.3-mile bridge with a $565 million price tag in 1971. By 1979, inflation raised the cost to $1.4 billion.
  • Studies estimated the bridge would carry 15,500 vehicles daily, with a $6 toll each way.
  • Plans included turning William Floyd Parkway into a four-lane expressway capable of handling 57,000 vehicles per day.

Modern Proposals

  • In 2016, Governor Andrew Cuomo reignited the idea with a feasibility study for a tunnel linking Long Island to the Bronx, Westchester, or Connecticut.
  • A 2018 Montreal company study proposed three crossing points:
    • Oyster Bay to Rye (18 miles, $8.5–$55.4 billion)
    • Kings Park to Bridgeport (30 miles, $13–$31.2 billion)
    • Wading River to New Haven (32 miles, $15.8–$32 billion)
  • In 2021, the North Atlantic Rail project included a 16-mile tunnel from Port Jefferson to Connecticut as part of a high-speed line from NYC to Boston.

A Bridge Too Far?

Despite bold ideas, escalating costs and environmental concerns have shelved every proposal to date. Whether it’s a bridge or a tunnel, the Long Island Sound link remains an enduring “what if.”

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