A Day’s Staycation on Shelter Island

A lot of young people think “The End” means Montauk; and it does, but there is also another end, and that end is Orient Point. Orient is great and all, but what if you wanted to do something a little different and get away for the day? Well, you can get on the North Ferry and go over to Shelter Island.

I personally love Shelter Island; my parents used to take me there a lot when I was a kid. We would drive around the island and stare in awe at the big houses. We’d also go to the beach and maybe get something to eat, and then call it a day. It was always nice going over to Shelter Island, because it seemed like a different world; it was so small and quiet. Now that I’m older I can still appreciate the quaintness of Shelter Island. Plus, it really does have nice beaches and places to eat, which is great for a 20-something who doesn’t want to spend an arm and a leg on a day trip.

First, you need to actually drive to Greenpoint and get on the ferry, either on foot or with your car. I recommend bringing your car, just in case, because certain places might be further away than you think. But if you don’t mind walking, by all means leave the car behind. Once you are on Shelter Island, before heading to the beach, drive or wander around and take in all the scenery. It really is a beautiful place and the mansions are exquisite. After you’ve been enraptured by your surroundings, then you can make your way to one of the beaches. Crescent Beach is the one my parents always used to take me to, but it can get a little crowded. In case Crescent Beach gets congested, try Shell Beach or Wade’s Beach. These are just as nice as Crescent and a little more secluded, and there are fewer children running around.

If you don’t just want to sit on a beach all day, then check out the Mashomack Preserve. It’s 22 miles of preserved land where you can hike and bird-watch. There is also a graveyard and an old manor house from the 1890s if you’re interested in a history lesson.

After lying on a beach, or hiking, especially, you’ll have worked up an appetite. There are many good restaurants to go to on Shelter Island, but I have two favorites. The first is the Ram’s Head Inn, which is where my parents used to stay if they were going over for the night, but they also used to take me there. It can be a bit pricey, but it is definitely worth it. I haven’t been there in quite a while, but from what I can remember the duck breast was always a favorite, as well as the butter poached lobster ravioli. The menu is not that big; however, everything on it is made to perfection.

The second restaurant that I can reccomend is The Chequit Inn. They are known for their seafood and that is what their menu is mostly compiled of. Every single time I go there with my aunt and uncle, we order the same things over and over again because they are delicious. I order the fried calamari to start, which is lightly breaded and crisp, and the seared tuna sandwich with wasabi mayo. The tuna is always nicely rare in the center and the wasabi gives it a great bite. My uncle orders the creamy, luscious clam chowder and the perfectly fried crab cakes. My aunt usually gets some kind of salmon, whether it is a special or from the regular lunch menu. I believe last time the special was a Caesar salad with blackened salmon on top, which looked amazing.

Finally, before getting back on the ferry, if you want something cool and refreshing, go to the Tuck Shop. They have the best ice cream on Shelter Island and their flavors are constantly changing. Their coffee ice cream happens to be my top pick.

As you can see, Shelter Island is a great place for 20-somethings to get away for a day or for overnight.


The Chequit Inn, 23 Grand Avenue 631-749-0018; Ram’s Head Inn, 108 Ram Island Drive 631-749-0811; Tuck Shop, 75 N Menantic Road 631-749-1548.

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