Shelter Island Travel Guide

Discover Shelter Island, New York's hidden gem with this comprehensive travel guide. Find the best places to visit, things to do, and places to stay with insider tips and advice.

Introduction to Shelter Island

Nestled in the eastern end of Long Island, Shelter Island is a charmingly quaint and picturesque island town that is often overlooked by tourists. Nevertheless, it has a lot to offer, from its peaceful beaches to its charming clapboard houses. With this comprehensive guide, you will discover Shelter Island’s hidden gems and popular attractions that make it a must-visit destination.

List of Places to Visit in Shelter Island

Culturally Important Attractions: Museums and Historical Places

If you’re a history buff, Shelter Island has several museums and historical attractions that will transport you back in time. One of the most famous places to visit to discover Shelter Island’s rich history is the Shelter Island Historical Society, which has several exhibitions and artifacts that depict the Island’s past. Additionally, the Havens Barn, built-in 1743 and listed on the National Register of Historic Places, showcases early colonial architecture.

Natural Attractions of Shelter Island: Outdoor Adventures and Scenic Views

If you’re an outdoor enthusiast, you’ll love the natural attractions of Shelter Island. The Mashomack Preserve, a 2,039-acre nature preserve, is a haven for nature lovers, bird-watchers, and hikers. It comprises fields, woodlands, creeks, and wetlands, making it a unique ecosystem. For scenic views of Shelter Island’s shoreline, head to Shell Beach. This secluded beach is perfect for a quiet picnic or a romantic walk with serene ocean views.

Hiking/Biking Routes of Shelter Island

With its rugged terrain, quiet roads, and stunning wilderness, Shelter Island is an ideal destination for hiking and biking enthusiasts. There are plenty of trails that offer peaceful and scenic routes. For those looking for a more strenuous hike, the Ram Island Loop trail is a challenging 4.8-mile trek that offers excellent views of the Shelter Island Sound. Alternatively, the Shelter Island Green Trail is an easier, 4.2-mile loop that’s great for all ages and skill levels.

Best Things to Do in Shelter Island: Activities and Tours

Whether you’re looking for adventure or relaxation, Shelter Island has an abundance of activities and tours to suit all tastes. You can go kayaking, sailing, paddle-boarding, or even horseback riding. For a tranquil and peaceful experience, spend the day on the secluded beaches, Mashomack Preserve, or visit the Sylvester Manor Education Farm.

Week-Long Itinerary for Shelter Island

Here is a sample itinerary for a week-long visit to Shelter Island:

Day Activity
Day 1 Explore Shelter Island Historical Society museums and exhibitions
Day 2 Spend the day hiking or biking on Shelter Island Green Trail
Day 3 Go wine tasting on the North Fork of Long Island
Day 4 Take a day trip to Greenport Village and visit the antique stores.
Day 5 Spend the day on the beaches of Shelter Island and go for a swim in the ocean.
Day 6 Go kayaking or paddle-boarding on Shelter Island Sound
Day 7 Go horseback riding at the Sylvester Manor Education Farm

Food and Drink Scene of Shelter Island

Must-Try Dishes

When you’re in Shelter Island, make sure you try the island’s classic seafood dishes. The island’s fresh seafood offerings are a delight to indulge in. A few must-try dishes include lobster rolls, clam chowder, oysters, and fried calamari.

Local Beverages

Head to Shelter Island’s vineyards, breweries, and cider houses that produce some of the best local drinks in New York. Visit the Pindar Vineyards, Shelter Island Vineyard, or try the Shelter Island Brewing Company if you love a good beer. Don’t forget to try the locally-produced hard cider at the Twin Stills Moonshine and Cidery.

Where to Stay in Shelter Island: Hotels, Hostels, and Guesthouses

From luxury hotels to cozy guesthouses, Shelter Island has plenty of accommodations to suit any budget and preferences. Some popular options include the Sunset Beach Hotel, the Ram’s Head Inn, and the Chequit Inn. For those looking for a more budget-friendly option, try the Airbnb rentals available on the island.

What to Buy in Shelter Island: Souvenirs and Local Products to Bring Home

While vacationing in Shelter Island, indulge in a little retail therapy, and bring home some souvenirs. Some unique products to buy include handmade pottery, locally-produced honey, and antiques. You can also visit the Shelter Island Historical Society’s museum shop to buy keepsakes that depict the island’s history.

Local Culture and Customs of Shelter Island

Shelter Island has several cultural traditions, including its famous Island Fair, a local festival that celebrates the end of summer. Islanders also come together every year to celebrate the annual Memorial Day Parade, the local farmers’ market, and charity events.

Best Time to Visit Shelter Island

The best time to visit Shelter Island is from late May to early September when the weather is warm, and all the attractions and restaurants are open. However, if you’re looking for a budget-friendly vacation, autumn and spring are the perfect seasons to visit, as you’ll get to enjoy more affordable hotel rates and lower airfares.

Do’s and Don’ts of Shelter Island


  • Do explore Shelter Island’s natural beauty.
  • Tour Shelter Island Historical Society’s Museum.
  • Do try fresh, locally sourced seafood.


  • Don’t litter on beaches or anywhere else.
  • Don’t leave your pets unattended.
  • Don’t be loud in the residential areas.

Safety and Health

Safety in Shelter Island

Shelter Island is a very safe place, but like any other place, it’s essential to be aware of your surroundings. Take the necessary precautions while driving on roads that are prone to accidents.

Health in Shelter Island

Visitors should follow standard health precautions, such as using insect repellent to avoid tick-borne diseases and sun protection to prevent skin damage.

Getting to Shelter Island: Transportation Options and Logistics

Airports Near Shelter Island

The closest airport to Shelter Island is the MacArthur Airport in Islip, Long Island, which is approximately 57 miles away. Alternatively, you can also fly into JFK or LaGuardia in New York City.

Bus Stations Near Shelter Island

The Long Island Railroad connects New York City with Greenport, Long Island, after which you can take a ferry or taxi to Shelter Island.

Other Options

You can also drive or take a ferry to Shelter Island. There are two ferries that run from Greenport, Long Island, to Shelter Island: North Ferry and South Ferry.

How to Get Around in Shelter Island

The best way to get around Shelter Island is by car or on foot. You can also rent bikes from several rental shops available on the island.

Where to Go Next from Shelter Island: Nearby Destinations and Excursions

Long Island’s North Fork, which is renowned for its excellent vineyards, beaches, and farms, is a perfect next stop after Shelter Island. Other popular nearby excursions include a trip to Montauk, the Hamptons, or Fire Island.


In conclusion, Shelter Island is a hidden gem that has everything a traveler could ask for, from its unspoiled natural beauty to its rich colonial history. Plan your next trip to Shelter Island, and you won’t be disappointed!