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The History of Trying to Connect Westchester and Long Island

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This 1965 rendition by design firm Madigan-Hyland shows the proposed Oyster Bay-Rye Bridge across Long Island Sound. The 6.1-mile crossing was to be a cable-stayed suspension bridge.
Illustration courtesy of MTA Bridges and Tunnels Special Archive

For nearly a century, people have been trying to connect Westchester and Long Island. Here’s the interesting history of why, despite the greatest of ambitions and the best of intentions, it never works.

In The Great Gatsby, F. Scott Fitzgerald refers to Long Island Sound as the “most domesticated body of salt water in the Western hemisphere.” He was no doubt thinking of the waterfront mansions, yacht clubs, and sailboat regattas that were the rage there in the 1920s. Yes, the westernmost section of the Sound, tucked between Southern Westchester and the north shore of Long Island, has been well-utilized by residents for hundreds of years, long before Fitzgerald cast a world-weary eye on the scene. Yet, “domestication,” or control, of the waterway has so far eluded a very specific and ambitious group.

Starting in the 1930s, developers and politicians have repeatedly proposed (and opposed) projects to link Long Island to Westchester (or Connecticut) by going over, or under, the Sound. The objective, of course, has been to bypass travel through the New York City area — something Long Islanders in particular, it seems, would stand to benefit from. Almost all drivers leaving the 118-mile, densely populated landmass must brave the Long Island Expressway and funnel onto a handful of metropolitan bridges. This trip can be a grueling experience, with cars often speeding dangerously or not moving at all — and that’s on a Tuesday.

Nonetheless, all of the tunnel and bridge proposals have met with the same fate — ending up, well, dead in the water. Before diving into the details of these nonstarters, a bit of perspective: The Brooklyn Bridge was built in 1883; the Williamsburg Bridge was completed in 1903; the Bronx/Whitestone Bridge debuted in 1939; and the Holland Tunnel opened to motorists in 1927. (The spiritual among us might want to say a prayer next time they traverse these structures… just kidding.)

The Oyster Bay-Rye Bridge was to complete the Interstate 287 beltway around the New York metropolitan area by connecting the Cross Westchester Expressway with the Seaford-Oyster Bay Expressway. Illustration courtesy of MTA Bridges and Tunnels Special Archive

The Oyster Bay-Rye Bridge was to complete the Interstate 287 beltway around the New York metropolitan area by connecting the Cross Westchester Expressway with the Seaford-Oyster Bay Expressway. Illustration courtesy of MTA Bridges and Tunnels Special Archive

It’s important to note that engineers and builders have been capable of these massive transportation feats for some time. It wasn’t completely pie-in-the-sky, then, when New York Senator Royal Copeland proposed the construction of an 18-mile bridge spanning Long Island’s Orient Point to Groton, CT, or Watch Hill, RI, in 1938. In fact, the bridge’s construction might have seemed more plausible then, when big infrastructure projects were being green-lighted and environmental concerns were not top of mind. Who knows what would have happened if Copeland hadn’t died that same year? His plan had garnered enough support to justify preliminary engineering studies, but enthusiasm faded without Copeland at the helm. Also, the nation had turned its attention toward the growing conflict in Europe, which may have contributed to the change in priorities, according to an engineering study from 2017 that looks at the Long Island Sound link from just about every angle. (This study will be analyzed later in the story.)

Some 20 years and a world war later, the Long Island-link idea resurfaced, in 1957, in the form of a two-bridge proposition, one on the east end of Long Island, connecting to Rhode Island, and another from Port Chester to Oyster Bay. New York State Public Works superintendent (and Cross River resident) Charles H. Sells was the catalyst behind this proposal. Then-Governor Averell Harriman nixed the notion, when (apparently dubious) feasibility studies suggested that traffic-volume predictions did not warrant moving forward.

It will surprise no one to learn that just a few years later, the traffic problems were becoming undeniable — most notably on the LIE and the Northern State Parkway. Cue master builder Robert Moses, who, as the driving force behind the construction of the Whitestone, Throgs Neck, Verrazzano, Henry Hudson, and more — was already a bridge-building legend. (In fact, it’s been widely reported, including in the pages of this magazine, that Moses biographer Robert Caro called him “power-hungry” and “bridge-obsessed.”) Moses revived and amended the Sells submission in 1965, proposing a $100 million bridge from Rye to Oyster Bay. His bid earned the support of the incumbent governor, Nelson Rockefeller, but even Moses could not turn the tide this time. Environmental regulations were starting to become a real obstacle in the infrastructure-construction process, unlike during Moses’ more prolific period. Also, his bridge was not popular with residents on either side of the Sound. Rockefeller ultimately withdrew his benediction, recognizing that it was political suicide.


Moses was no longer attached, but the project was only mostly dead. Similar ideations were proposed again, in 1968 and 1972, with the potential spans joining Rye to Oyster Bay, New Rochelle to Sands Point, and Rye to Glen Cove. By 1973, Governor Rockefeller had rejected them all, yielding to local opposition. Of course, these were locals with the political clout that comes from piles of NIMBY money. One bridge route was drawn almost directly over Rye’s Manursing Island. Enough said.

Political memories are apparently short, as Governor Hugh Carey decided to wade back into the cross-Sound-bridge waters in 1979 (when traffic on the LIE wasn’t getting any less dense). He initiated a study to consider five different alignments, all starting farther out east on Long Island, connecting with Connecticut or Rhode Island. One of the possible bridges was a $1.4 billion, 24.6-mile span from Orient Point to Watch Hill. (The longest auto bridge in the world currently is the Lake Pontchartrain Causeway, in Louisiana, which runs 24 miles. The bridge has its own police force, and its officers are often called upon to escort disoriented drivers across the span.) But after the report was completed and reviewed, state planners decided that all five alignments were bridges too far, adding that ferries, though slow, were preferable. (The Cross Sound Ferry travels daily, except on Christmas, from Orient Point to New London, and has done so since 1975, with smaller enterprises sailing the route long before that. The Port Jefferson Ferry to Bridgeport has been traversing the Sound since the 1800s.)

The subject seemed permanently sunk, and for years, ferries quietly remained motorists’ sole city-avoiding route on and off Long Island. But once again, an ambitious visionary decided that something should be done. This time, the plan was to go under the water. In 2008, Long Island developer Vincent Polimeni put forth the first serious tunnel proposal, and he wasn’t kidding around. In fact, he tapped Hatch Mott MacDonald, an engineering firm that worked on the famed railroad Chunnel, which spans the English Channel, for input. Polimeni’s aim was to build a massive tunnel connecting Rye to Nassau County. The behemoth structure was to comprise two tubes containing three lanes of traffic each, with a smaller tube running along the middle to allow for emergency access. The structure was designed to be 18 miles long, making it the longest undersea cars-only tunnel in the world. The tunnel was estimated to cost some $10 billion, although Polimeni was looking to fund the project privately, and his firm footed the bill for the feasibility study. His intent was to charge a $25 toll both ways, estimating that some 80,000 cars would pass through the tunnel daily. In addition, the sale of naming rights and advertising space were floated as possible revenue generators.

The bridge represented in this 1965 study would have significantly altered the layout of several Rye neighborhoods. Image courtesy of MTA Bridges and Tunnels Special Archive

The bridge represented in this 1965 study would have significantly altered the layout of several Rye neighborhoods. Image courtesy of MTA Bridges and Tunnels Special Archive

Polimeni admitted that his plan was initially met with “smirks and skepticism,” when put forward at a New York State Senate meeting, according to an article in the Boston Globe. But the developer added that many people “became intrigued” upon examining the specifics more closely. Interestingly, the Globe headline for the Polimeni piece labeled the tunnel “an auto shortcut to New England.” While this reads as a Boston-centric perspective, Polimeni mentioned this particular rerouting of traffic as a justification for the tunnel. Not surprisingly, then-mayor of Rye Steve Otis reportedly argued that tunnel traffic flowing into his town would render “our roads nonfunctional.” Oyster Bay supervisor John Venditto did not deliver a hard “no” to the project, although he admitted that it did seem “unrealistic.” Underscoring the breadth of this undertaking, Polimeni predicted that even with all systems go, the tunnel wouldn’t be completed until 2025. So, what happened? Consider this: In 2008, one of Polimeni’s prospective partners in the project was Bear Stearns. The Great Recession swept both the financial institution and Polimeni’s plan out to sea.

While Polimeni has since died, his son Michael has been widely quoted as saying his father’s meticulously researched plan was feasible but perhaps “a bit before its time.” However, it was only a few years later that Governor Andrew Cuomo thought the time was right. He commissioned Montreal-based engineering firm WSP to a conduct a lengthy study analyzing the possibility of a cross-Sound link. Completed in late 2017, this $5 million, 80-plus-page opus seems to leave no stone unturned in terms of considering the tunnel’s potential impact on traffic, the economy, and the environment.

The main takeaways: The proposal identified multiple potential configurations for the link. A number of the alignments stretched from central or eastern Long Island to Connecticut — the majority of which were deemed unviable. Two of the configurations deemed worthy of advancing to the next phase included a tunnel from Rye to Oyster Bay and a bridge/tunnel combo along the same route. According to the WSP study, the 18-mile Westchester-to-Long Island hybrid would start with a tunnel leading away from land, emerging onto a six-mile bridge over the Sound and back down into a tunnel for a mile before egress onto Rye roadways.

Newspaper columns from towns in both Westchester and Long Island reported the same type of local opposition that vexed every proposal throughout the years: too expensive and potentially devastating to the suburban status quo and the environment.

The report contends that tunnels are less environmentally damaging than bridges, as they burrow well under the wetland areas near shorelines and surface beyond them into less environmentally sensitive areas. But tunnels are also more expensive. The price tag for Cuomo’s tunnel-only version, according to the study, was $55 billion. WSP engineers did suggest a money-saving (and anxiety provoking?) alternative: a $31.5 billion one-tube tunnel, with two traffic lanes in each direction stacked on top of each other. The hybrid proposal came in at $43.5 billion. Meanwhile, the bridge-only model, at just $8 billion, was dismissed as too disruptive to local neighborhoods and fragile ecosystems, despite its cost-effectiveness. As you would imagine, toll prices were analyzed for all prospective alignments. The study based its projections on the understanding that higher tolls would decrease usership, but lower tolls would decrease revenue. The sweet spot was determined to be a both-way $25 auto toll (higher for trucks), which would generate $556 million annually, with about 74,000 cars passing through each day by 2040, when the tunnel was expected be a well-established part of the traffic flow. (Of course, given the drastic changes that 2020 has wrought, predicting 2040 seems somewhat unrealistic.)

At first, Cuomo appeared buoyed up by the report. “We should continue to pursue a tunnel from Long Island to Westchester or Connecticut,” he said in defense of the idea at a State of the State Address in 2018. “It would be underwater. It would be invisible. It would reduce traffic on the impossibly congested Long Island Expressway and would offer significant potential private investment.” He even progressed to soliciting requests for expressions of interest (REOI), asking qualified engineering and construction firms to submit preliminary bids on the project. While Cuomo continued to publicly express support for the tunnel, his administration unceremoniously dropped the idea within the same year. Leading up to this announcement, of course, newspaper columns from towns in both Westchester and Long Island reported the same type of local opposition that vexed every proposal throughout the years: too expensive and potentially devastating to the suburban status quo and the environment. Others argued that the money would be better spent shoring up our existing, and aging, infrastructure.

A notable perspective appeared in the Hartford Courant. Norman Garrick, a civil-engineering professor at UConn, pointed out that the auto-only tunnel was actually a notion whose time had passed, “an old-fashioned approach to transportation,” as it included no mass-transit feature. One must wonder, though, in this (not so) brave new world of the pandemic, with profound economic hardships and remote work sessions likely to become the norm, if the cross-Sound bridge/tunnel idea will bubble up again anytime soon.