The roads they never built across the North Fork

We all know the Long Island Expressway doesn't lead to Greenport and Orient — this is actually a Route 58 sign — but what you might not know is that throughout the 1950s and 1960s many local officials hoped it would. (Credit: Grant Parpan photo illustration)
We all know the Long Island Expressway doesn’t lead to Greenport and Orient — this is actually a Route 58 sign — but what you might not know is that throughout the 1950s and 1960s many local officials hoped it would. (Credit: Grant Parpan photo illustration)

Driving to the end of the Long Island Expressway and exiting onto the western edge of Route 58, Riverhead’s commercial capital, it’s difficult to imagine that a plan once called for the island’s longest road to extend into Southold Town.

But drawn on a map titled “Expressway Plan 1959 County Planning Board” are two thick red lines that run from the Riverhead Town line to Old North Road in Orient. One line indicates eastbound Long Island Expressway traffic. The other shows traffic lanes heading west. 

In this vision of the expressway, Long Island’s major thoroughfare stretched across almost the entire North Fork, running east-west and paved so far north that drivers would have been able to see Long Island Sound at certain points.

When residents from Riverhead to Orient banded together recently to block a plan to send 3,000 more heavy-duty trucks across the North Fork annually via the Cross Sound Ferry, it stood as a reminder of both the limited capacity of our principal roads and how easily that could have changed over the years. So, too, did a recently withdrawn plan to expand the United Riverhead Terminal into a gasoline distribution center, which had the potential to add even more trucks to our roadways.

Scanning through town and county documents, historical society archives and newspaper articles from the past 80 years makes it obvious that the idea of having two bucolic highways to transport motorists across the North Fork was never exactly the plan.

Instead, proposals to expand the expressway, to connect Long Island to New England with a series of bridges and to widen County Route 48 were once the norm for our growing region. Even during the Great Depression there was a road plan for East Marion that would have seen 18 streets built off Main Road, many of them connected by traffic circles. We’ve all heard of the road less traveled, but it’s these roads never built that would have dramatically altered the North Fork.

“It probably would have been the death knell for the region’s rural character,” Bob DeLuca, president of the environmental organization Group for the East End, said of these abandoned proposals. “For all the complaining people do about traffic, the sprawl that accompanies such projects outweighs any short-term traffic benefits.”

From as far back as 1953, when the plan for the Long Island Expressway was first pitched, Riverhead was proposed as the final exit. But almost immediately local officials were calling for an expansion into Southold Town.

While it’s hard to imagine today that anyone in Southold would have supported such a proposal, the supervisor at the time was among its biggest proponents. At an April 1954 meeting of the Suffolk County Board of Supervisors, Southold Town Supervisor Norman Klipp drafted a resolution to build the expressway out to Orient Point, something he said was supported by the entire Town Board.

The resolution, which also included the expansion of Sunrise Highway on the South Fork, was approved by all but the Southampton supervisor. The bill stated that the entire county was “experiencing a remarkable growth and the eastern section is also sharing in the expansion of population and industry.” 

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