If you plan to do some Shelter Island hiking or scenic walking, you’ll have wonderful options on the island. Not only is Shelter Island an incredible beach town, but it also houses some of the most beautiful trails on the entire East End.
Yes, Shelter Island is a true hiker’s paradise. For one, it’s completely stunning from every vantage point. It also possesses acres of natural wonders, like miles of coastline, picturesque creeks, as well as woodlands and fields with native species, all deserving of a true hiker’s journey (not to mention some amazing photos!) Beyond classic trails it also offers wide open spaces and preserved lands that are dog-friendly and hiking appropriate, too.
Most trails on Shelter Island are dog-friendly with the exception of Mashomack Preserve*. Visit the Shelter Island Animal Control website for more information about the rules and regulations about permitted areas, including:
- All dogs are required to be licensed.
- Dogs are prohibited on Crescent Beach, Wades Beach and Shell Beach between Memorial Day and Labor Day. Dogs are allowed at some Town landings.
- Dogs must be leashed or under immediate and reasonable control of their owners.
- No noise disturbances due to excessive barking.
Read on as we share some of the best Shelter Island hiking spots around the island. We’re bringing you the most beautiful trails that locals love, and we think you will, too.
*The hero photograph of Mashomack Preserve in this article is by Doug Young. See more of Doug’s photography in “10 Shelter Island Restaurants to Try During Your Stay” article here.
Enjoy Picturesque Shelter Island Hiking at Mashomack Preserve
NO DOGS ALLOWED
The “Jewel Of The Peconic,” this massive preserve borders 11 miles of pure coastline and is widely considered one of the richest habitats in the entire Northeast. It’s of little wonder, then, why tourists and locals flock to this vast woodland for a proper Shelter Island hike. Covering over 2,350 acres, Mashomack features interlacing tidal creeks, beautiful oak woodlands, sweeping, prairie-esque fields, freshwater marshes and underwater habitats. There are up to seven color-coded trail maps ranging in length and difficulty, so there’s something for everyone, including coastal and bluff trails as well as prime wildlife viewing. Be sure to check out the visitor’s center prior to your hike to discover more about the natural elements that make up the East End.
79 S Ferry Rd, Shelter Island, NY 11964
Old Nursery Woodlands Preserve
This 24.37-acre property is practically hidden in plain sight, even though it’s the geographical center of the Island. It runs along the back of many homes, stores and other structures along St. Mary’s Road near North Ferry Road. Bring your pup and meander through its meadow, virgin forest and overgrown nursery stock. The backstory is that Old Nursery Woodlands is actually part of the 1,000 acres that George Havens purchased from Nathaniel Sylvester II in 1700, and it passed to his son William Havens and to others. According to a 1909 map, its principal owners were Scudder Smith and T. M. Haisey and it passed through others thereafter.
Access on St. Mary’s Road near North Ferry Road
Turkem’s Rest Trail
Dating back hundreds of years, this nearly six-acre property on South Midway Road is bordered by Fresh Pond to the North and Dickerson Creek to the South. About 30 percent of the property features tidal wetlands with spartina grass and native vegetation. The other portion is woods with wild cherry, oak and black locust trees. The land dates back to 500 to 1500 A.D. when a community of Native Americans from the Algonkian-speaking clan called Manhassets, lived on the shores of the Pond. You can access the preserve from Midway Road by following a circular trail. Bring your binoculars to spot migratory geese, blue herons, snow egrets and cormorants. Halfway through the trail, you’ll happen upon the largest body of freshwater on Shelter Island, Fresh Pond.
60 S Midway Rd, Shelter Island, NY 11964
Bunker City County Park
After a 23-year battle between the town of Shelter Island and Hay Beach’s developers, this 35-acre pristine tract of land was purchased by Suffolk County in 1993. Bring your dog and walk along the varied flora and fauna, including protected species such as Eastern Prickly Pear Cactus, Red Cedar plus numerous other wildflowers, shrubs and grasses. Bunker City County Park is also a nesting area for Piping Plover and features 42 acres of coastal preserve marked by red cedars and native grasses and shrubs. Access this preserve via Menhaden Lane off Gardiners Bay Drive. You’ll need a resident permit if going by car. The beach is great for walks and exploring. At night it is one of the best places for stargazing as well.
Enter at Menhaden Lane off Gardiners Bay Drive
Coecles Harbor Marine Trail
OK so it’s not a traditional Shelter Island hike per se, but if you break out your paddleboard or kayak, you can embark on a five-mile marine trail that runs along the shoreline of salty marshes filled with fiddler crabs below and osprey nests above. Think of it like a nature walk on water, where following a loop around Taylor’s Island, you’ll come across the Smith-Taylor Cabin, which serves as a landmark for boaters navigating these waters. Built by New York City magnate S. Gregory Taylor at the turn of the 20th century, the one-room log cabin was later deeded to Shelter Island Town and is now enjoyed by the public. It’s the perfect spot for a picnic before hitting the water again.
18 Hudson Ave, Shelter Island, NY 11964
This quiet yet stunning enclave is perfect for catching some quality Shelter Island hiking, but it’s a quiet trail where you’ll likely have the entire area to yourself. Find your path at the Menhaden Lane parking lot (remember to have your Shelter Island Town Beach sticker) and head southeast to a peaceful 42 acres of beach scrub on your trail.
Continue along this pebbly beach, where you’ll snag ocean views from all sides, and head southeast until you reach a road that leads to Little Ram Island. From there, you’ll get sweeping views of Gardiner’s Bay, the Atlantic Ocean and all the spectacular beauty this island offers. You’ll approach Ram’s Head Inn on your right as you follow Ram Island Drive and loop around for about two more miles.
Watch for Bald Eagles at Sylvester Manor
DOG-FRIENDLY (LEASH REQUIRED)
With its 225 acres awash with gardens, farm fields and wooded trails, Sylvester Manor is a lovely way to take in some Shelter Island hiking. This farm dates back to the 17th century and features paths behind the property’s manor house that leads to a burial site believed to house the remains of 200 people who were slaves or indentured servants.
Follow the short trail to farm fields and the marshy area of Gardiner’s Creek, commonly known as the former site of Native American camps prior to European settlements. You might catch a deer or bald eagle so keep those binoculars handy.
80 N Ferry Rd, Shelter Island, NY 11964
Shelter Island Hiking at Sachem’s Woods
Locals love Sachem’s Woods, a one-mile loop located in the middle of the island. It’s quiet, lesser known than some of the other Shelter Island trails and are beloved for their lowkey quality and quiet beauty. Access the trail from North Midway Road near the intersection of Bowditch Road. Just know that this Shelter Island hiking spot doesn’t have bathrooms, garbage cans or parking. So anything you take in must be taken out.
Take a Detour at Arshamomaque Pond Preserve
DOG-FRIENDLY (LEASH REQUIRED)
OK so this is a bit of a detour from proper Shelter Island hiking, but just a ferry ride to the North Fork will bring you into the town of Greenport, which houses this part of the Long Island Pine Barrens Maritime Reserve. This unique complex is one of the most valuable coastal and marine ecosystems in the nation and centers on the Peconic Bays, which is a federally designated National Estuary. It’s got rich wildlife in its woodlands, open meadows, ponds and tidal wetlands and has over 2,200 feet of shoreline frontage on the pond itself.
Upon arrival, head over to Osprey Overlook, a short trail that’ll give you an opportunity to watch ospreys as they patrol the skies in search of fish. You can spot several nests around the pond as well as ducks, herons, egrets and ibis. Remember to stay on the designated trails and dogs must be leashed.
Arshamomaque Pond Preserve
920 Chapel Ln, Greenport, NY 11944
Whether you’re looking for an all day adventure or a low key walk with friends, Shelter Island hiking trails have something for everyone. You can easily spend your time amidst the trees, animals and the beautiful flora and fauna that inhabit the island and embark on journeys whose one time inhabitants date back hundreds of years. There’s so much to discover on a hike through Shelter Island. Just remember to bring your sunblock, stay hydrated and always check for ticks.
*Disclaimer: Visit the Shelter Island Animal Control website for more information about the rules and regulations about permitted areas, including: All dogs are required to be licensed, dogs are prohibited on Crescent Beach, Wades Beach and Shell Beach between Memorial Day and Labor Day. Dogs are allowed at some Town landings. Dogs must be leashed or under immediate and reasonable control of their owners. No noise disturbances due to excessive barking.