Eastern Long Island, Mystic, CT – Beaches and Car Ferr

A Vacation Based on Curiosity

Did you ever wonder what’s at the very eastern tip of Long Island? What happens when you travel out the end of Queens, then Nassau County, past the cemeteries, and just keep on going? No? Well I did – on an island seemingly disjoined from the rest of the country, past the cities, past the Hamptons even – there’s … the end of the highway as the roads get smaller and smaller followed a lot of farms, vineyards, and some really nice beaches and very chilled people. Modern technology makes the visit a breeze – not sure I would have attempted it before AirBNB, Waze, and even Google Maps reviews of locations.

Kite flying at Orient Beach State Park

At the end of Long Island, the island forks into two – in the north fork is Orient Point and Greenpoint which have the Long Island Sound to the north with Connecticut on the other. In the south fork you’ll find Montauk. The drive between the two is 1.5 hours! There’s a car ferry which will take you over to Shelter Island between the two – we didn’t do this because we took the ferry the “other way” – between Orient Point and New London, Connecticut. This ride is about an hour twenty minutes, leaves punctually on time, and takes your car with you. Once on board, they sell food with quite a bit of the packaged goods and drinks being kosher. Bring a board game or activities for your kids because looking out the boat wasn’t quite enough for the entire ride.

Beautiful Beaches; No Crowds

A flower in one of the pebble beaches.

We went in June – the weather was perfect and everything was empty. You won’t kosher food in the area (nearest kosher restaurant seems to be in Great Neck on the other side of Long Island – 1 hr 45 min drive if you’re lucky), but you won’t really find much in the way of food or supermarkets at all. There’s a 7-11 in Greenpoint which is the “city” in the area, the “city’ portion filling up about a block and a half with a marina where you can rent boats. Greenpoint has it’s share of beaches such as the 62 step beach which, after descending probably that amount of steps (didn’t count it) you’re on a pebble beach interspersed with large rocks – this is on the north side. Beaches on the south side, such as Klipp Marine park (put Manhasset ave in your GPS and drive to the end), are a 5 to 10 minute drive at most because the north fork is so narrow. A friendly local selling firewood told us the south side is always a bit warmer.

Sixty-two step beach so named because it takes that many steps down the stairs to get to it.

Then, traveling east from Greenpoint towards Orient Point, the land narrows to be not much more than the one lane road with a lake on one side and Truman Beach on the other – yet another nice beach. Interesting point of fact: if you use Optimum Online there are WiFi hotspots at every one of these places so far – seems to be the only internet in town so free WiFi was everywhere. This is almost purely a pebble beach with pebbles of all sorts of colors … and variations of smooth and rounded shapes.

Orient Beach State Park

Finally, go all the way to the eastern tip and you’ll reach Orient Beach State Park. Travel down a few miles of a single lane road with water on both sides of you, traveling generally southwest, and you reach one of the more interesting beaches I’ve encountered. There’s a beautiful beach with some sand and some pebbles with nearby picnic tables for at least a few hundred people. We did actually see a few people coming and going, but very few during our June visit. Weather was beautiful and the wind kept our kite in the air the entire time we were there. A portable propane grill was my weapon of choice for cooking and the seagulls enjoyed our food too. On the beach are playgrounds for the kids, swinging chairs, and if you’re so inclined, areas to fish. One note about this beach: no swimming is allowed anywhere!

A deer running across Truman beach. The first case in law school I read was about “giving chase” to a fox on the “beaches of queens” – apparently there are still animals on the beaches at the other end of Long Island.

The parking lot and beach / picture area right there are not nearly the end of the park. From there, you can walk down miles of narrow beach, the beach stretching on both sides of a very narrow peninsula which is kept in place by the plant life – cactus and others that survive salt-water sprays. On one side are ocean-like conditions, and the other a lagoon-like condition with very still water. Being with kids, I wasn’t able to take the trail through the miles of empty beach too far, but my kids did make the observation that walking in the lagoon area wasn’t technologically swimming – this is also the area where the rent kayaks in the higher seasons.

That basically covers it for the north fork – it’s pastoral and a whole lot of beaches. We did about four in one day and you can’t go wrong with kids at a beach. The best kids activities are the free ones.

Mystic Seaport

A model at Mystic Seaport

Drive your car on the ferry to New London, CT and suddenly you’re in “civilization” again. It’s a really city and from there you can make your way to Waterbury or New Haven with sizable Jewish communities. Also about a 12 minute drive away is Mystic, CT with Mystic Aquarium and Seaport. I haven’t been to the former but the latter is fun for a trip with any kid, say, about 12 or under. It’s an old seaport where boats were actually constructed under about the Great Depression. They had the wise idea to turn it into a museum and tourist destination. You sort of have to “find your adventure” here because a) it’s very big (they keep adding to it), and there’s a lot of interesting things to see but b) there’s a lot of things that won’t interest many people. Some is “hands on”, some is silly, some is lectures, some is looking at buildings but with some “breaking in” you can figure it out. E.g. the rope making demonstration where you turn the rope and see how it’s made was fun and educational … the singing while they put a stuffed cow on a boat and dropped it in the water … eh.

The actual Gerda III which saved the lives of about 300 Jews during the Holocaust – a gift from the government of Sweden

Then there are places like an old house where you see someone cooking in pots directly over a fire “before” stoves (not quite true though perhaps they weren’t popular in New England in the time period they’re trying to represent). Basically, it depends on the guide you find in the particular area. A lot tend to have narrow knowledge or aren’t so forthright with information so you have to ask questions and get them talking. That’s how I got the clock maker talking about his extreme socialist views … okay kids, time to go to the next building …

One interesting thing of note is they have the actual boat, the Gerda III which was used to ferry Jews from Denmark to Sweden, saving about 300 from the Nazis before a larger convey of boats was eventually used to saved almost all the Jews of Denmark. I heard the story before but it was quite a surprise to stumble upon the boat itself!

Claire’s Corner Cornucopia in New Haven, CT

If you’re making the rounds from New York City through Long Island and back through Connecticut (or the other way around…), be sure to stop at Claire’s Corner Cornucopia in New Haven. It’s not far off the highways – we always stop here when traveling to the northeast. It’s a dairy restaurant that caters to a the local college crowd and others – it also happens to be kosher. They have all sorts of baked goods, pastas, eggs, and things that I’ve never really heard of that probably every vegan out there knows. Also, plenty of gluten free. It’s one of those health conscious places I suppose – I’m an omnivore and appreciate it just the same because it’s very good quality food.

Put your car on a boat to get from Long Island to Connecticut


In short, with the exception of Mystic Seaport, it’s a great car trip that you can do from the New York or Boston area for a few days that won’t set you back very much while your kids will have a great time. You can stay in Connecticut to be near minyanim and go over to Orient Point for a day trip or rent a house in the Orient Point / Greenpoint area. Enjoy. Feel free to ask questions in the comments.


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3 Responses

  1. Benjamin Hirsch says:

    I never heard of a car fairy. Is it bigger than Tinker Bell?

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