Long Island Crossing

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The Long Island Crossing was a proposed idea to span the Long Island Sound and connect New York's Long Island with Connecticut and/or Rhode Island. These proposals were intended to provide access between Long Island and points north that would bypass New York City.

The idea included building a variety of bridges.

A bridge connecting Mamaroneck in Westchester County, New York, with Sands Point on Long Island. This bridge would lead to a possible spur of Bronx-White Plains Expressway^{[citation needed]} onto Long Island via the unbuilt Western Nassau Expressway in Nassau County.
A bridge connecting Rye in Westchester County, New York, with Oyster Bay on Long Island. This bridge would be an extension of Interstate 287 onto Long Island via the existing Seaford-Oyster Bay Expressway in Nassau County.
A second bridge connecting Rye to the City of Glen Cove on Long Island. This bridge would've connected to the Glen Cove Arterial Highway on Long Island.
A bridge connecting Asharoken, New York to either Stamford, or Norwalk, Connecticut. This bridge would have connected to the unbuilt Babylon-Northport Expressway in Western Suffolk County. In Norwalk, it would've lead to the already upgraded U.S. Route 7, while in Stamford, it would more than likely have connected to the unbuilt Pound Ridge-Stamford Expressway, and lead back into New York.
A bridge and possible dam connecting Poquott, New York to Bridgeport, Connecticut. This bridge would've connected the unbuilt Suffolk County Road 110 (A.O. Smith Turnpike) to CT 8-25.
A bridge connecting either New Haven, Connecticut or East Haven, Connecticut, with Shoreham, New York, on Long Island. This bridge would be an extension of Interstate 91 which would continue through Long Island via the already existing William Floyd Parkway.
A bridge connecting Riverhead, New York with Guilford, Connecticut. This bridge would have connected at an alternate extension of Interstate 495 to Exit 59 on the Connecticut Turnpike.
A bridge connecting Old Saybrook, Connecticut with East Marion, New York. This bridge would have connected the east end of the Long Island Expressway with CT 9 near Interstate 95 in Connecticut.
A causeway and bridge connecting Orient Point, New York, with Rhode Island along a series of islands between the North Fork of Long Island and an eastern terminus at Interstate 95 in Rhode Island.

All nine ideas were discussed in the 1950s, 1960s, and 1970s, but all were canceled. Some were reconsidered during the 1990s, but the New York State Department of Transportation backed away from the idea in belief that it would not relieve congestion, however, Long Islanders seem to favor a bridge but New Englanders are not very supportive of the idea, claiming that it would benefit Long Island at their expense.