Discover the Town of Shelter Island

Montauk Point Lighthouse

East End Getaway has curated a guide to the towns across the North and South Forks, highlighting some of the best of what to see, do, and what the insiders know. This information will help you map and plan your next getaway to the East End of Long Island. Today, we take you inside the town of Shelter Island

Brief Overview of Shelter Island

Shelter Island is an 8,000 acre island located between the North and South Forks of Long Island and is only accessible by ferry. The ferry is allocated for both walk-on passengers and automobiles and only takes between 5-8 minutes, respectively, to arrive at Shelter Island from the Hamptons or North Fork. Much of Shelter Island is a part of nature preserves, with nearly one third of the island is owned by The Nature Conservancy. Shelter Island has very little traffic year round and visitors may also notice that there are no traffic lights or signals on the island. 

Shelter Island is located just two and a half hours away from New York City via the North Ferry, the most direct and fastest way to get to NYC. 

Shelter Island is a great destination for families and couples of all ages looking to tour and visit the restaurants, shops, camping sites, museums, beaches, nature trails and preserves, and array of outdoor events held all year long. 

Shelter Island has many miles of beautiful beaches. Beaches on the island include Crescent Beach, Gibsons Beach, Shell Beach, Wades Beach. Wades Beach, for example, is considered to be a very family friendly beach. 

How to Travel to Shelter Island

There are several convenient ways to travel to Shelter Island. From Manhattan, the most direct and fastest route is by train from Penn Station with several direct trains throughout the day. There is a train station in Greenport as well as in Bridgehampton. The Greenport train station neighbors the North Ferry, with easy walking access. 

There are also bus routes from Manhattan with the Hampton Jitney and their luxury line, the Hampton Ambassador. The Hampton Jitney has both a North and South Fork line, with a preliminary stop in Manorville. The Hampton Jitney and Ambassador buses stop in Greenport and Bridgehampton, among many more stops along the North and South Forks. 

If you are driving from New York City, the most direct route is via I 495, then merging onto Route 25 in Riverhead, continuing through the north fork until you arrive in Greenport Village. You will see a sign that directs you to route 114/the North Ferry. Proceed on board. Car, bicycle, and walk-on passengers are permitted and the ferries run seven days a week year round. 

Traveling from Connecticut? The Cross Sound Ferry travels between New London and Orient Point and offers a full, daily timetable schedule. Orient Point is approximately ½ hour from Shelter Island through East Marion and Greenport via the North Ferry. 

What is particularly unique about Shelter Island is that you can easily access either the North or South Fork from Shelter Island via ferry. It takes about a half hour to travel from North Haven/Sag Harbor to Greenport via both ferries by car. Route 114 is the main road that cuts through Shelter Island and is easily accessible by bike as well. Route 114 continues through Sag Harbor and into East Hampton until it perpendicularly connects with Montauk Highway in East Hampton Village. 

In need of cash to round out your ferry trip? There is a Chase Bank off of Route 114 midway through Shelter Island. 

Places to Go

Shelter Island has several notable places of interest for individuals and families of all ages. For those who wish to discover more about local history and culture, visit the Shelter Island Historical Society and the Shelter Island Public Library around the corner from Shelter Island Slice. 

A must is stopping at one of the farm stands on Shelter Island. These include The Farmstand at Sylvester Manor, Sep’s Farm, and Havens Farmers’ Market. Note that most of these farm stands and markets are open seasonally, or through the holiday season. 

Havens Farmers’ Market is held throughout the latter part of spring and throughout the summer. It is traditionally held on Saturday mornings beginning at 9am from Memorial Day to Labor Day weekend on the grounds of the Shelter Island History Center. The market features a wide mix of local vendors and purveyors, with past years’ participants including Goodale Farms, The Blue Duck Bakery Cafe, Peeko Oysters, and The Perfect Pickle. 

Specifically for families with young children, places on Shelter Island to visit include Sylvester Manor educational farm, Shelter Island Historical Society, Whale’s Tale for ice cream and mini golf, and Mashomack Nature Preserve for the ideal bird watching setting. 

Rams Head Inn is a very family oriented hotel and property, where they offer a wide range of lawn games, have onsite play equipment, and a sprawling backyard to run around and play on. A trip to the nostalgic Shelter Island Heights Pharmacy is also a must to pick up any necessities like snacks, sunscreen, bubblegum, games, and more.  

Where to Dine on Shelter Island

Shelter Island has a variety of casual and fine dining restaurant establishments. Many of these restaurants are family owned and operated, and have been in business for decades. 

Vine Street Cafe is an upscale and chic American restaurant known for their fresh produce, seafood, and wine selection. Dinner is served year round. Notable dishes include their Country Fried Chicken, Moules, Miso Salmon, and Harissa Spiced Lamb. A grab and go food shop is attached to the restaurant, perfect for specialty food items and gifts. 

Isola, which translates to island in Italian, is an Italian restaurant and pizzeria in the heart of Shelter Island and within walking distance to The Chequit and North Ferry. Isola serves dinner year round and offers both indoor and outdoor seating as well as an expansive bar. Dishes to try include their Crispy Eggplant Parmesan, Polenta Funghi, Crispy Brussel Sprouts, and PEI Mussels. 

Léon 1909 is a southern French provencal restaurant open year round with indoor and outdoor seating. The restaurant’s menu rotates with the season and serves French and Italian fare. Dishes to note include Scallop Crudo, the Léon Burger, and Tuna Tartare. Leon is located close to The Pridwin Hotel and Sunset Beach Hotel. 

Shelter Island Slice is a popular local’s hangout that serves pizza, Italian subs, cannolis, wine, beer, and soda year round. Lunch and dinner are served Tuesday-Saturday. Look out for Sunday football specials and lunch specials. 

Stars Cafe is a breakfast and lunch cafe famous for their sandwiches, smoothies, juices, and pastries as well as their own freshly brewed coffee. They are located adjacent to Isola and are also within walking distance of The Chequit and the North Ferry. Outdoor and limited indoor seating is available. Open seven days a week from 6am-4pm. 

Annual Activities on Shelter Island

Shelter Island is known for hosting a wide selection of annual events that are perfect for everyone to enjoy. Events are held year-round.

Popular events include the Shelter Island 10K & 5K Run/Walk held annually in June, the Shelter Island Fireworks held annually in July, and the Shelter Island Chamber of Commerce Art Show and Craft Fair held in August. The hotels and restaurants, including Rams Head Inn, The Chequit and The Pridwin, regularly host live music and entertainment on weekends as well as regularly throughout the summer season. 

Lodging on Shelter Island

We recommend the following hotels and bed and breakfasts on Shelter Island. Please note that some properties are only open seasonally. 

The Chequit is a historic hotel in the heart of Shelter Island overlooking Dering Harbor within walking distance of the North Ferry. It has been rated as one of the best hotels in the USA and recently celebrated its 150th anniversary. Guestroom amenities include king-sized beds with Frette sheets, towels, slippers and robes, luxurious rain showers, Malin+Goetz bath amenities, a mini-fridge, and more. The Chequit has two onsite restaurants and a cafe. The Tavern is open year-round.

Ram’s Head Inn is also a sprawling, historic waterfront hotel and restaurant on Ram Island Drive. The hotel offers seventeen guestrooms and is open year round. The restaurant offers indoor and outdoor seating with an expansive bar, curated cocktail list, live music, signature dishes, and more. 

Sunset Beach Hotel is a chic and seasonal boutique hotel and restaurant on Crescent Beach. The hotel offers twenty waterview rooms with luxurious amenities and accommodations. Lunch and dinner are served at their restaurant and bar Wednesday-Monday in-season. The hotel also has an onsite boutique gift shop. 

The Pridwin by Cape Resorts is a stunning, newly renovated hotel property on Crescent Beach. The hotel offers spacious nautical rooms and cottages for couples and families alike. The Pridwin has an onsite restaurant and bar on the second floor of the main building with a beautiful deck overlooking the water, a spa, fitness center, meeting space, gift shop, and more. The onsite spa has a full menu of treatment options including massages, facials, and body treatments. The hotel also offers daily water sport activities in season, an onsite tennis court, wellness classes, and family activities. 

Seven on Shelter is a luxury boutique B&B on Stearns Point Road. The B&B offers spacious king and queen guest rooms. Amenities include contemporary art and book collections in every room, Bath amenities from The Cold Spring Apothecary, luxury products by Pré de Provence, beach accessories, lawn games, a swimming pool with a cabana and outdoor fireplaces, daily breakfast beach basket, and more. 

(cover image of Mashomack Nature Preserve on www.sevenonshelter)

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