Staying at the Shelter Island House in Shelter Island, NY

Staying at the Shelter Island House in Shelter Island, NY

Loving weekend getaways as much as I do, I’m always on the hunt for the best ones near NYC. When I read about the Shelter Island House, I knew that this would be the perfect quick trip from the Manhattan.

Shelter Island, New York

Shelter Island is a small island that sits between the North and South forks of Long Island. It’s reachable only by ferries and its inhabitants are of the wealthier persuasion, as noted by the seaplanes, beautiful houses, and private boats speckled about the island.



But it’s easy and fun to visit by all, which was why I had been wanting to go there for a while. The island is only 12.5 square miles and consists of beaches, golf courses, wetlands, forests, and lots of marinas. Year-round residents only number about 2,400 (2010 census), but swells to 12,000 during the summer.



In general I prefer to stay at boutique hotels or at a B&B because I think you get a more personalized, local experience. This was how the Shelter Island House had caught my eye.



With an historic past, lovely amenities, and customer service that goes above and beyond, the Shelter island House was the perfect place for a couple of days away as I explored the bucolic Shelter Island. This was my experience.


The Shelter Island House – The Boutique Hotel

The beautiful and award-winning hotel that is nestled on the shore’s of Long Island’s coast was the perfect getaway from NYC. Established in 1945, the Shelter Island House was one of the first hotels on the island. It’s situated on a quiet street near Sunset Beach and near enough to the main area of town if you have a car.



When I first got there, my impression was that it was comfy, quaint, and felt like a home. For history buffs like me, I loved that the hotel maintained its original architecture from the 1940s. Even so, it still felt modern, but had enough of a small town charm to make it a relaxing respite.



I also noticed right away that everything was illuminated by natural light. Each room was airy and bright, with blue accents against a very clean white.


The lobby


Our room was also full of natural light and overlooked the backyard. It was a good size and I got excellent sleep in the bed. My compliments to the cleaning staff of this place. Everything was immaculate.



They also had my favorite brand of potato chips in the room, North Fork Potato Chips. It was one of the first things that I noticed because I’m a pig like that. Whenever I am in the eastern end of Long Island I hunt this brand of chips down.


Some of the main amenities at the Shelter Island House included the below. Unfortunately, when we went it was too cold to go in the pool, but it looked like it would’ve been a lot of fun.

  • Outside Pool (Open Seasonally)
  • Poolside Bar with Grab n’ Go Menu
  • On-Site Tavern
  • Outdoor Petanque Courts (lit for night-time play)
  • Gift Shop
  • Complimentary Bicycle Rentals
  • Complimentary Beach Umbrellas, Chairs & Towels
  • Complimentary Wi-Fi all throughout the property



As nice as the inside was, the outdoor part of the property was one of my favorite parts. I loved, loved that they had a Bocce Court. I used to play it all the time at family reunions. Plus, David is Italian so it was nice. When we played I won both times. Just saying.


The backyard and front porch were great for sipping wine, tea, and coffee in the morning or afternoons. It was quiet enough where you could curl up with a good book, which seemed very appropriate for Shelter Island. The whole island just screamed writer’s hideaway. This would hold true in the winter as well, since the patio had an open fire pit.



There was a bunch of activities in the backyard that you could do if you’re into games. Otherwise, at night most of the guests and locals come for the restaurant, The Tavern, and would hang out in the big bar area in the back.




The Top Things to do In Shelter Island

Since David and I had arrived in the early part of the morning, we wanted to get started on exploring Shelter Island. From my research, the top things to do in Shelter Island are as follows:

  1. Mashomack Preserve
  2. Kayaking
  3. The beach
  4. Paddle board
  5. Sylvester Manor Educational Farm
  6. The Shelter Island Historical Society Museum

Since we went at the end of September, the summery, beach activities were out. So David and I decided to go to Mashomack Preserve and drive around the island to explore.


Authentic Mexican Food at Maria’s Kitchen

Of course, before any of that the first thing on our mind was food. We jumped in the car and headed to Maria’s Kitchen. A local had recommended this place as a must-try. Now, I’m a big fan of Mexican food. Since I live in NYC I can brag that I’ve been able to eat some pretty authentic and delicious dishes. We were told that Maria’s is a very traditional Mexican restaurant.


They were right. And it was so good! I didn’t take pictures of the food because we pounced on it too quickly, but take my advice, if you’re looking for a quick meal, go to this place. They don’t have a full seating area so think of it more as a take-out spot.


Mashomack Preserve

No wonder Shelter Island is a popular honeymoon spot for locals. It’s also a nature lover’s haven. About 1/3 of the island is set aside as a nature preserve. Although the island is very modern now, the preserves are why it still maintains so much of its natural landscape. No where was this more evident than at Mashomack Preserve.



When we got there we were shown a map of the all the trails that we could take. We didn’t have enough time before the park closed at 5pm to do the trail that would have led us to a renovated manor house, so we chose the thirty minute route. It was really cute because the trail had little storyboards for children that could be followed along the way.


This preserve was pretty and serene. I loved the views of the water. Back in the 17th century, recorded history shows that this land was part of the Caribbean sugar trade. The water views from the Mashomack Preserve must have been what Shelter Island looked like to those sugar traders, i.e. without all the docks and private boats.


Shelter Island Heights

Strolling through Shelter Island Heights got us acquainted with the most charming and historical part of the island. In the early 19th century, the local landowner had called this area Prospect. Now, Shelter Island is listed on the United States and New York State Register of Historic Places. The centerpiece of Shelter Island Heights is at the Union Chapel, which was built in 1875.



In fact, many of the houses in the area have architecture that was either from or influenced by the 1870s. But here’s the best part. One of the people who had contributed to the design of this area was Frederick Law Olmstead! He was the person who had designed Central Park and the Emerald Necklace in Boston. Pretty cool for little Shelter Island.


Rams Island

The Manhanset Native American tribe, in their native language, called Shelter island “an island protected by islands.” Ram’s Island (Big Ram) and Little Ram Island are two offshoot islands within Shelter Island. Many islands.

Everything in Shelter Island was really close, so it was a short, scenic drive to get to the Ram islands. This definitely seemed to be the area where the most opulent homes were that could sell easily in the millions. It wasn’t hard to see why. These two islands felt even more secluded than the rest of the island, so it was truly a great location to build a beautiful home where you could get away from it all and look at the water – of course while still being close enough to civilization if you get bored of that.



Two causeways connect these islands with Shelter Island. As we drove through I swear I saw some Osprey nests on the top of the telephone poles.



One side of these islands face Gardiners Bay and has a sandy, yet sometimes rocky beachfront. It also has bluffs, dips, and open views of the water. The other side that faces Coecles Harbor looks out at Mashomack Preserve, the inlets, marinas, and Taylor’s Island.


My favorite part about Rams Island was getting to Reel Point, the peninsula at the southern tip of Big Ram Island. It’s a natural barrier that protects Coecles Harbor. No one was there when we went. The only thing at the end of the street, where Reel Point sits, was a large, prominent looking house that overlooked the beach. I wondered who lived there.


Shelter Island Beaches

The best stretch of beach is Hay Beach on Menhaden Lane. Other public beaches include Crescent Beach, Wades Beach, Shell Beach, and Fresh Pond. The Shelter Island House was walking distance from Crescent Beach.



The Tavern at Shelter Island

On the second night we dined at Shelter Island House’s restaurant, The Tavern. Incorporating the local fisherman and farmers, the seasonal menu served a scrumptious array of New American style foods with al fresco or fireside dining. We were sat next to the fireplace, which looked like the coziest spot in the room for cold, wintry nights. Since it was cool, but not a cold night, they still had outside seating available.

In the morning before it opened

The Tavern was split into two halves: the bar area and the dining area. I was told that this is one of the only restaurants of it’s type that stays open year round. You could tell that a lot of locals came here for dinner.

David and I were starving so we couldn’t wait to eat. I ordered the Half Roasted Chicken with sautéed spinach, fingerling potatoes, and herb jus. Very good. David had the Grilled New York Strip with mashed potato, and blistered asparagus. We split the sautéed  cauliflower, which was my favorite. It had this Kung Pao type of sauce on it.


The Shelter Island House Packages

If we had went later in the fall, I also would’ve like to have participated in their Wine & Harvest activities. They worded it best when they said, “Some folks say the sidewalks roll up after Labor Day and that there’s just no action on the East End after the summer season. We challenge these naysayers and want to tell everyone what fall on the East End of Long Island is all about!”



Sunsets on the beach in warm sweaters, apple picking, Harves Family Farm and Vineyard, hiking the fall foliage at the preserve, and going harbor seal watching are just a few of the fall activities that you could do from the Shelter Island House.



Their was also their romantic getaway packageA Taste of the East End. This package “explores local artisan wine and edibles and celebrate the harvest of the Hamptons and North Fork.” Even though I was with David we didn’t try that. But along with the Fall Festival, I’d certainly like to if we go back!


How to Get to Shelter Island

Coming from New York City, we had two choices for getting to Shelter Island. The first was drive, which we did. In retrospect, we should’ve taken the Long Island Railroad to Greenport and jumped on the North Ferry, which was right there! But no matter. We were able to take our car on the ferry from Greenport. The ferry was only an 8 minute ride and $11 one way with a car.



Overall, Shelter Island was a bucolic, quiet getaway. If you go during the summer, it’s a perfect beach vacation, but reserve ahead of time. To book at the Shelter Island House, visit their site. It also sells out quickly, so book fast!


What do you think of Shelter Island?




  • Caroline N

    This place and Block island are definitely on my list!

  • Madi

    Long before you wrote about it, I’ve noticed the wonderful natural light of this place. It gave me a sense of serenity.
    Then I imagined myself all curled up in a comforter on the patio with a steamy cup of coffee, no service on my phone, with my laptop writing incessantly what will become the next bestselling book of the decade. Dream big or go home, right?
    It made me want to take a sabbatical from my job and live there for a while.

    • We’re 100% with you on the writing incessantly part!

  • Herb

    I’ve lived on Long Island for 23 years and I can’t believe that I’ve never been to Shelter Island! It looks absolutely picturesque there and doesn’t sound too difficult to get to. I’m definitely adding it to my must-visit list in the spring. Thanks for the post!

    • Hi Herb – yeah, it’s pretty easy to get to. From NYC it’s just the LIRR or car. Or if you’re coming from the north, you can take a ferry to Long Island from CT.