Shelter Island, New York

Shelter Island
A tranquil shoreline scene on Shelter Island, New York, where a narrow inlet of calm water winds through a pebbled beach toward the Shelter Island Sound. The horizon features a serene mix of distant landforms and oyster beds under a bright summer sky, reflecting the island’s unspoiled natural beauty and quiet coastal charm. File photo: Maria T Hoffman, licensed.

Shelter Island, New York, is one of Long Island’s most unique and tranquil destinations – a secluded island oasis nestled between the North and South Forks at the eastern end of Suffolk County. Accessible only by ferry, this 8,000-acre island is surrounded by Shelter Island Sound, Greenport to the north, and North Haven to the south. With no bridges or highways connecting it to the mainland, Shelter Island offers an idyllic escape where natural beauty, colonial charm, and a slower pace of life are preserved in harmony.

The island is often described as a blend of history and nature. Roughly one-third of Shelter Island is protected land, thanks to the Mashomack Preserve, a 2,000+ acre nature sanctuary maintained by The Nature Conservancy. Mashomack features a diverse range of ecosystems – woodlands, tidal creeks, salt marshes, and freshwater wetlands – making it a haven for bird watchers, hikers, and nature enthusiasts. Its extensive trail system provides one of the most peaceful and scenic outdoor experiences anywhere on Long Island.

Originally inhabited by the Manhanset people, Shelter Island was purchased by English settlers in the 17th century and quickly developed a reputation as a farming and shipping hub. In the 19th and early 20th centuries, it transformed into a seasonal retreat for affluent families from New York City, many of whom built grand summer homes that still stand today. The town’s historic character is preserved in its charming Victorian inns, vintage homes, and quaint, family-owned shops and restaurants.

Shelter Island consists of several hamlets, including Shelter Island Heights, a designated historic district known for its gingerbread cottages and water views. Shelter Island Heights is also home to the island’s largest marina, a vibrant summer hotel scene, and the Shelter Island Country Club, offering golf with a view. The ferry terminal from Greenport lands directly in this area, making it a natural hub for visitors and residents alike.

Beaches and boating are central to life on Shelter Island. Popular local beaches include Crescent Beach (also known as Sunset Beach), which features soft sand, calm waters, and one of the island’s most iconic beachfront hotels and restaurants. Wades Beach, on the south side of the island, is ideal for families with its lifeguards and gentle shoreline. Shellfishing, kayaking, sailing, and paddleboarding are popular pastimes in the surrounding waters, and many homes come equipped with private docks or access to community moorings.

Despite its small size and rural nature, Shelter Island offers a surprisingly rich array of amenities and services. Local businesses range from gourmet markets and art galleries to garden centers and boat repair shops. Dining options are upscale but unpretentious, with many establishments sourcing fresh, local ingredients. Seasonal events like the Shelter Island 10K Run, the Green Expo, and various farmers markets reinforce the island’s strong community spirit and environmental values.

Shelter Island is also known for its deliberate balance between development and conservation. Zoning regulations, strict environmental oversight, and an active civic culture have helped the island resist overdevelopment. Many of the island’s homes are tucked away on quiet roads or hidden behind hedgerows and trees, contributing to a sense of privacy and exclusivity. The real estate market here tends to be robust, with both summer rentals and high-end homes in demand, particularly during the warm months.

While the island’s year-round population is under 3,000, that number swells significantly in the summer as seasonal residents and visitors arrive. Yet even at its peak, Shelter Island remains far less crowded than its neighboring Hamptons to the south or the more commercialized North Fork. It’s a place where locals wave from their cars, cyclists cruise along winding roads, and the sound of boats in the harbor replaces city noise.

In summary, Shelter Island is a destination defined by peace, prestige, and preservation. Whether you arrive by ferry from Greenport or North Haven, you’ll find yourself stepping into a world where nature and tradition still reign supreme. For those seeking a refined but unspoiled escape, Shelter Island is truly one of Long Island’s best-kept secrets.

Top Things to Do on Shelter Island, NY

1. Mashomack Preserve

One of Shelter Island’s crown jewels, this 2,350-acre nature preserve offers over 11 miles of trails through salt marshes, coastal creeks, woodlands, and freshwater wetlands. It’s a top destination for hiking, bird watching, and photography. The preserve is managed by The Nature Conservancy and is considered one of the richest natural habitats in the region.

2. Crescent Beach (aka Sunset Beach)

Located on the western shore near Sunset Beach Hotel, this is one of the island’s most popular beaches—great for swimming, lounging, and catching incredible sunsets. There’s a beach bar and restaurant nearby, offering a chic, lively summer scene.

3. Wades Beach

This family-friendly beach features calm waters, lifeguards, and bathroom facilities. It’s a great choice for those with kids or anyone looking for a quieter day on the sand.

4. Boating and Kayaking

The island’s waterways, inlets, and harbor areas are ideal for sailing, kayaking, and paddleboarding. Rentals are available seasonally, and many accommodations offer water access. Coecles Harbor and Dering Harbor are especially scenic boating spots.

5. Shelter Island Heights Historic District

Take a stroll through this charming neighborhood featuring 19th-century Victorian homes, cozy inns, and boutique shops. It’s also where the North Ferry docks from Greenport, making it the island’s unofficial “downtown.”

6. Fine Dining & Coastal Eats

  • Vine Street Café – A local culinary favorite offering upscale American cuisine.
  • Sunset Beach Restaurant – Trendy, waterfront dining with views of the Sound.
  • 18 Bay – A seasonal farm-to-table restaurant with a rotating Italian tasting menu.
  • Marie Eiffel Market & Café – Popular for breakfast and lunch with a French flair.

7. Shelter Island Country Club (Goat Hill)

A historic 9-hole public golf course with panoramic views of the island. It’s casual, affordable, and one of the few places you can golf on Shelter Island.

8. Shelter Island Historical Society

Located on the grounds of Havens House, the Historical Society offers a glimpse into the island’s rich colonial and maritime past. It frequently hosts exhibits, lectures, and family-friendly events.

9. Perlman Music Program

Founded by world-renowned violinist Itzhak Perlman and his wife Toby, this elite summer music school brings in gifted string musicians from around the world. The campus often hosts public concerts during the summer months.

10. Biking the Island

With relatively quiet roads and beautiful vistas, Shelter Island is perfect for cycling. Bring your own or rent a bike and take a scenic loop that includes beaches, preserves, and historic landmarks.

11. Ferry Rides

Both the North Ferry (to Greenport) and South Ferry (to North Haven/Sag Harbor) offer scenic rides that are brief but memorable. Whether you’re arriving, leaving, or just joyriding, the ferries offer gorgeous views of the island’s shoreline.

12. Boutique Shopping

Explore Shelter Island’s small collection of boutiques and galleries. Expect handmade goods, beachwear, antiques, and locally made crafts—perfect for unique souvenirs or gifts.

Shelter Island Ferry Information

Getting to and from Shelter Island is part of the experience, with two scenic and efficient ferry services operating year-round. Both ferries accommodate vehicles, bicycles, and walk-on passengers, and reservations are not required.

North Ferry (Greenport to Shelter Island Heights)

  • Route: Greenport (North Fork) ↔ Shelter Island Heights
  • Crossing Time: ~7 minutes
  • Schedule: Ferries run every 10–15 minutes, year-round.
  • Operating Hours:
    • Summer: Approx. 6:00 AM to midnight (later on weekends)
    • Off-Season: Reduced hours but still frequent (early morning through late evening)
  • Notes: Walk-on passengers can board directly near downtown Greenport. Fare is collected on the Shelter Island side for round-trip.

📍 North Ferry Website

South Ferry (North Haven to Shelter Island)

  • Route: North Haven (South Fork/Hamptons) ↔ Shelter Island
  • Crossing Time: ~5 minutes
  • Schedule: Ferries run every 10–15 minutes, with minimal wait times.
  • Operating Hours:
    • Daily: Approximately 5:00 AM to midnight
    • Summer Weekends: Extended service hours
  • Notes: Fare is collected on the North Haven side. Ideal route for travelers coming from Sag Harbor, East Hampton, or Montauk.

📍 South Ferry Website

Tips for Travelers:

  • No reservations are needed for either ferry.
  • Payment is usually cash or credit at the booth; prices vary based on vehicle size.
  • Both ferries operate 365 days a year, including holidays.
  • Summer weekends can be busy—arrive early if traveling with a vehicle.
  • Bicycles and motorcycles are welcome on both ferries.