On a clear day you can see it from the Connecticut shoreline (only about 20 miles away). But actually getting to Long Island often involves a very long, out of the way journey.
Maybe you’re going to LaGuardia or JFK. Or a Met’s game at Citi Field. Perhaps you’ll want to see the Belmont Stakes at Belmont Park. Or a Nets game in downtown Brooklyn (yes, officially a part of Long Island). Or maybe you fancy a summer beach trip to the Hamptons or Montauk. They’re all on Long Island… along with eight million residents.
With so much to do on Long Island one wonders why it’s so hard to get there from Connecticut.
Assuming you’re driving, most people take the usually-crowded (and forever-under-construction) Throgs Neck or Whitestone Bridges, always a delight.

Photo from Wikimedia Commons
Whitestone Bridge
Or if you’re a real masochist you could drive to the RFK (Tri-Borough) Bridge connecting the mainland Bronx to Queens. Want to avoid paying tolls? You’ve got to first go into Manhattan, then take the 59th St., Manhattan, Williamsburg or Brooklyn Bridges. You’ll save a few bucks but it will cost you a lot of time.
History buffs will remember that developer czar Robert Moses once proposed a bridge and causeway from Rye (in Westchester County) to Oyster Bay (in Nassau County). The 1966 plan would have seen a 6.1 mile cable-stayed bridge costing $150 million ($1.4 billion in today’s inflated dollars). Seen as an extension of I-287 it would have connected with Long Island’s Seaford – Oyster Bay Expressway. Of course, the plan never went through.

Image from MTA archives
The never-built Rye-to-Oyster Bay Bridge
But in 2007 the idea was revived, this time as a two-tube tunnel with three lanes in each direction. This would have been the longest in the world. Price tag: up to $16 billion. That, too, never went anywhere.
There are two ferry boats connecting Connecticut and Long Island: the Bridgeport-to-Port Jefferson ferry (a 75 minute crossing first established by P.T. Barnum in 1883) and the New London-to-Orient Point ferry (an 80-minute cruise).
Both are well patronized, especially in the summer. The Bridgeport ferry is even building a 300-foot-long new boat, “The Long Island,” due early next year.

The new ferry, due in March 2024
Amtrak has been dreaming of a cross-Sound railroad tunnel as a high-speed rail alternative to its current tracks along the Connecticut shore, but those ideas are still in the “hopeful and maybe” but unfunded stage.
What is a reality now is a much better rail connection between Metro-North and the Long Island Railroad. No longer do you have to schlep from Grand Central to Penn Station (a taxi ride or two subways).
Now you can arrive at GCT and just go downstairs to Grand Central Madison, the LIRR’s new station 140 feet under Vanderbilt Avenue. You can even buy a through-ticket, say, from New Haven to Montauk: a six hour trip costing only $25.75 off-peak, one-way.
So yes, you can get to Long Island from the nutmeg state. It just won’t be easy or fast.
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Contributed photo
Jim Cameron
Jim Cameron has been a Darien resident for more than 25 years. He is the founder of the Commuter Action Group, sits on the Merritt Parkway Conservancy board and also serves on the Darien RTM and as program director for Darien TV79. You can reach him at CommuterActionGroup@gmail.com.