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United States
New York
Suffolk County

Shelter Island

The best walks and hikes around Shelter Island

4.5

(8)

81

hikers

19

hikes

Hiking around Shelter Island, located between Long Island's North and South Forks, offers diverse landscapes for outdoor activities. The island, approximately 27 square miles, features protected wetlands, nature preserves, and extensive coastlines. Trails wind through habitats including tidal creeks, mature oak woodlands, prairie-like fields, and freshwater marshes, with generally flat terrain. The region is characterized by coastal paths, serene woodlands, and expansive nature preserves.

Best hiking trails around Shelter Island

  • The most popular hiking route is Mashomack Preserve loop —…

Last updated: June 23, 2026

19

hikers

#1.

Mashomack Red, Yellow, Green and Jone C. Coles Loop

8.91km

02:18

50m

50m

Embark on the Mashomack Red, Yellow, Green and Jone C. Coles Loop for a moderate hike that spans 5.5 miles (8.9 km) with a gentle elevation gain of 157 feet…

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Moderate

10

hikers

2.81km

00:44

10m

10m

Explore the Mashomack Red Trail, an easy hiking route that guides you through a diverse landscape of freshwater marshes, tidal creeks, and serene oak forests. This pleasant path offers intimate…

Easy
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1

hikers

5.56km

01:26

30m

30m

The Grace Estate offers a delightful escape into nature, winding through a diverse landscape of oak-pine forests and unique kettle-hole wetlands. You'll discover centuries-old cart tracks, pass by the preserve's…

Easy

The Linda Gronlund Trail Loop offers a delightful escape into nature, winding through a diverse landscape of coastal and pine barrens habitat. You'll experience the tranquility of white pinewoods and…

Easy

The Chatfields Hole via Northwest Path offers a serene journey through a historic woodland, perfect for a quick nature escape. You'll wander through an oak forest, where towering pitch pines…

Easy
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Popular around Shelter Island

Running Trails around Shelter Island

Road Cycling Routes around Shelter Island

Cycling around Shelter Island

Tips from the Community

Zachary
April 29, 2025, Two Holes of Water Park

You can walk almost all the way around the ponds of this small park on wide, well-maintained trails that lead you deeper into the South Fork trail systems. There are a couple parking spots along the road with views of the water.

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Grace Estate Preserve offers over 500 acres of water and woods for exploring. It has miles of trails and nice views of Northwest Harbor, and it's ideal for bird watching, hiking, running, and photography. The park is open year-round, from sunrise to sunset. Note that swimming is prohibited, and there is no lifeguard on duty. Dogs are welcome on the condition that owners pick up after them.

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Alex
July 24, 2024, Nicoll's Creen

Nicoll's Creen is a marshy bay, part of Mashomack Preserve. This area is great for birdwatching and a scenic spot for a break.

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Grace Estate Preserve, on Long Island, is a natural sanctuary, encompassing diverse habitats and scenic trails.

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Frequently Asked Questions

What kind of terrain can I expect on Shelter Island hiking trails?

Shelter Island's hiking trails are characterized by generally flat terrain, winding through protected areas, along shorelines, and across open fields. You'll encounter diverse ecosystems including coastal paths, serene woodlands, and expansive nature preserves, with habitats like tidal creeks, mature oak woodlands, prairie-like fields, and freshwater marshes.

Are there any easy hiking trails suitable for beginners on Shelter Island?

Yes, Shelter Island offers several easy trails perfect for beginners or those seeking a relaxed stroll. For instance, the Arshamomaque Preserve Trail loop is a 1.7-mile path through woodlands, and the Elizabeth A. Morton National Wildlife Refuge also features an easy loop trail leading to a scenic beach.

Can I bring my dog on the hiking trails on Shelter Island?

While many areas on Shelter Island are dog-friendly, it's important to note that dogs are generally not permitted in the Mashomack Preserve, which covers a significant portion of the island. Always check specific preserve rules before bringing your dog. For other trails, dogs are often welcome on a leash.

What natural features or landmarks can I see while hiking on Shelter Island?

Shelter Island's trails offer a variety of natural beauty. You can explore the diverse habitats of Mashomack Preserve, including tidal creeks and oak woodlands, or visit the historic Sylvester Manor Educational Farm with its old-growth forests and shorefronts. Other notable spots include the observation towers at Arshamomaque Preserve overlooking a pond, and the scenic beach at Elizabeth A. Morton National Wildlife Refuge. You might also spot wildlife like birds, deer, and wild turkeys.

Are there any circular hiking routes on Shelter Island?

Yes, many of Shelter Island's trails are designed as loops, offering convenient circular routes. Examples include the Mashomack Preserve loop, the Arshamomaque Preserve Trail loop, and the Grace Estate Preserve loop, which winds through varied terrain.

What is the best time of year to go hiking on Shelter Island?

Shelter Island offers enjoyable hiking year-round. Spring brings blooming flora and active birdlife, while summer provides warm weather for coastal walks. Autumn showcases beautiful fall foliage, and winter offers quiet, serene trails, though some facilities might have reduced hours. The generally mild climate makes it a pleasant destination for outdoor activities in most seasons.

Are there family-friendly hiking options on Shelter Island?

Absolutely. Shelter Island has many trails suitable for families. The easy loop at Elizabeth A. Morton National Wildlife Refuge is known for its friendly birds and leads to a beautiful beach, making it a great option for children. Shorter, less strenuous loops like the Arshamomaque Preserve Trail loop are also ideal for families.

What do other hikers enjoy most about hiking on Shelter Island?

The hiking experiences on Shelter Island are highly rated by the komoot community, with an average score of 4.4 stars from 6 reviews. Hikers often praise the island's serene woodlands, diverse natural preserves, and the peaceful coastal paths that offer a refreshing escape into nature.

Is parking available at Shelter Island trailheads?

Parking is generally available at the entrances to many of Shelter Island's preserves and trailheads. For popular spots like Mashomack Preserve, designated parking areas are provided. It's always a good idea to check specific preserve websites or local signage for detailed parking information before your visit.

Are there any permits or fees required to hike on Shelter Island?

For most public preserves and trails on Shelter Island, there are no specific permits or fees required for hiking. However, the Mashomack Preserve, managed by The Nature Conservancy, may have specific entry guidelines or suggested donations. It's advisable to check their official website for the most current information regarding access.

How can I get to Shelter Island and its trailheads using public transport?

Shelter Island is accessible by ferry from Greenport on the North Fork or North Haven on the South Fork. Once on the island, public transportation options are limited. While some local services might exist, reaching specific trailheads often requires a car, bicycle, or taxi. Planning your route in advance is recommended.

Are there any less crowded hiking trails on Shelter Island?

For a quieter hiking experience, consider exploring some of the smaller preserves. Sachem's Woods offers a serene, mile-plus loop through an oak and beech forest, known for its low-key quality. Other options like Arshamomaque Preserve or the trails on Ram Island (including Section 9/Dressel Preserve) can also provide a more tranquil setting away from the busiest spots.

Most popular routes around Shelter Island

Easy hikes around Shelter Island

Most popular attractions around Shelter Island

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