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.
Last updated: June 23, 2026
19
hikers
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…
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…

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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…
5.52km
01:25
30m
30m
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…
3.20km
00:50
20m
40m
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…
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Popular around Shelter Island
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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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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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.
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.
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.
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.
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.
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.
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.
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.
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.
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.
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.
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.


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