Did You Know?
The Paumanok Path runs 125 miles from Rocky Point out to Montauk Point, crossing the towns of Brookhaven, Riverhead, Southampton, and East Hampton before it ends at the lighthouse. Several of the trails in this guide are stretches of that same path, which means an easy afternoon loop can put your boots on the same footpath as somebody a week into walking the whole thing.
For those interested in hiking, the Paumanok Path provides a fantastic opportunity to experience the diverse landscapes while hiking.
Hiking through these landscapes not only connects you with nature but also offers a chance to meet fellow hiking enthusiasts.
The East End is not one landscape. It is a half dozen of them pressed up against each other, and hiking is the only way to feel where one ends and the next begins. Glacial ice shaped the ridges, the kettle holes, and the two long forks of sand running east into the Atlantic. The trails are where all of that becomes easiest to read.
Enjoy hiking along the bluffs and taking in spectacular views of the Sound.
The maritime forest offers unique spots for hiking, where you can discover diverse flora while hiking.
Hiking along the salt marshes gives a peaceful experience filled with wildlife sightings.
The coastal plain ponds are a tranquil destination for a relaxing day of hiking.
Hiking through the dunes and moorland at Napeague offers a unique coastal adventure.
Start with the ground you want under your boots.
Don’t forget to plan your hiking routes to include the best views and landscapes.
Bluffs and Sound overlooks – the north shore of Riverhead and the North Fork, where the land drops off to a stony beach.
Maritime forest – red cedar, black-jack oak, and prickly pear at Orient, Noyac, and out in Montauk.
Salt marsh and tidal creek – the quiet water edges at Cutchogue, Southold, and Mashomack.
Coastal plain ponds – the rare chain of kettle ponds strung between Sag Harbor and the ocean.
Dunes and moorland – the shifting sand at Napeague and the bluffs at the far end of Montauk.
Jump to a Region
The guide runs west to east, from Riverhead out to Montauk Point, the way most people arrive. Use the links below to go straight to the stretch you are headed for.
- Riverhead – Sound bluffs, beach access, and short nature walks
- North Fork – creek, marsh, pond, and Sound-edge walking
- Shelter Island – longer preserve trails and ferry-day planning
- South Fork – wildlife refuges, coastal plain ponds, and swamp boardwalk
- Montauk – dunes, woods, bluffs, and the longest trail networks out here
- Make a Day of It, or Stay the Night – three built routes with somewhere to eat and somewhere to sleep
- Before You Go – ticks, parking, dogs, and what the trails do not provide
Riverhead
As you hike in Riverhead, take the time to appreciate the stunning scenery along the trails.
Wildwood State Park is a great choice for hiking, with trails that offer varied terrain.
For hiking enthusiasts, Hallock State Park Preserve offers diverse environments to explore.
Cranberry Bog County Nature Preserve provides a perfect loop for hiking and enjoying nature.
Indian Island County Park is another excellent hiking location with beautiful scenery.
Riverhead gets treated as the place you drive through on the way somewhere else. That is a mistake if you like walking. This is where the Sound bluffs run highest and where the river country begins.
Hiking on Shelter Island allows you to discover the area’s unique natural beauty.
Wildwood State Park, Wading River – Trails run through hardwood forest along the top of a Sound bluff, then drop down a long stairway to the beach. The walk out is gentle. The climb back is the part you will remember.
Hallock State Park Preserve, Northville – Two hundred twenty-five acres of woods, bluffs, Hallocks Pond, and nearly a mile of Sound beachfront. The preserve straddles the Riverhead and Southold town line, so it works as either the last stop on a Riverhead day or the first on a North Fork one.
Cranberry Bog County Nature Preserve, Riverhead – What remains of an abandoned cranberry-growing operation, now a loop around Sweezy Pond through wetland and pine forest with views of the Little Peconic River. The bog reads differently in every season, and it is the reason to come.
Indian Island County Park, Riverhead – Where the Peconic River empties into Flanders Bay. Easy walking through pine and oak with the water in view for much of it.
Local Tip: Cranberry Bog and Indian Island sit close enough together to walk both in a day and still get to downtown Riverhead to dine.
North Fork
North Fork walking is short and layered. The preserves here are small, and they are almost all built around water, either a creek running out to the bay or the Sound waiting at the end of the path.
Mashomack Preserve is ideal for hiking with its extensive trail networks and rich wildlife.
Downs Farm Preserve, Cutchogue – Fifty-one acres of woodland and salt marsh along Downs Creek, and home to the archaeological site of Fort Corchaug, a palisade fort built by the Corchaug people in the seventeenth century and now a National Historic Landmark. The Town of Southold maintains the trails. The fort remains themselves are protected and kept off the path, but the loop and its signage tell you what you are walking past.
When hiking, consider exploring the grounds of Sylvester Manor.
Arshamomaque Preserve, Southold – A level boardwalk-and-woods walk that works well for birding when you want an hour outside and nothing more strenuous than that.
Inlet Pond County Park, Greenport – A compact county park with a kettle pond, a short trail network, and a bluff overlook out to the Sound, close enough to Greenport to fold into a village afternoon.
Quogue Wildlife Refuge is a wonderful place for hiking with its various trails.
Consider hiking at Elizabeth A. Morton National Wildlife Refuge for an immersive nature experience.
Orient Beach State Park, Orient – The end of the fork. A long, low spit of land runs out into Gardiners Bay through a maritime forest of red cedar, black-jack oak, and prickly pear cactus. Flat, exposed, and unlike anywhere else on Long Island.
Long Pond Greenbelt is perfect for hiking with its serene landscapes and abundant wildlife.
Sagg Swamp Preserve offers a unique hiking experience through its wetlands.
Cedar Point County Park presents hiking trails with spectacular views of the bay.
Local Tip: Orient rewards an early start. The trail out to the point has almost no shade, and the light on the bay side is best before the day heats up.
Shelter Island
Montauk’s trail networks are perfect for hiking enthusiasts looking for adventure.
Shelter Island holds the largest single block of protected land on the East End, and getting there by ferry sets the pace for the whole day.
Hiking at Hither Hills State Park offers breathtaking views and a variety of trail options.
The trails at Theodore Roosevelt County Park provide great hiking opportunities for all levels.
Shadmoor State Park is an attractive option for hiking with its scenic bluff-top trails.
Mashomack Preserve, Shelter Island – The anchor of any East End hiking trip. The Nature Conservancy protects more than two thousand acres here, edged by eleven miles of coastline. The trail network runs from short loops to longer routes that will fill a day, moving through mature oak woodland, tidal creek, freshwater marsh, and open field. It is also one of the strongest birding sites in the region, particularly during spring and fall migration.
Hiking at Montauk Point State Park allows you to enjoy the stunning shoreline views.
Sylvester Manor, Shelter Island – Grounds and farm walking at a historic site whose interpretation addresses the Indigenous, enslaved, and indentured people connected to the land. A completely different kind of walk from Mashomack, and better paired with it than chosen against it.
After a day of hiking, relax and enjoy the local cuisine in nearby towns.
Local Tip: The ferry crossing is part of the trip rather than an obstacle to it. Plan the day around the boat and you will spend a lot less of it watching the clock.
South Fork
Between the villages and the ocean, the South Fork holds some of the rarest habitat in New York State. Much of it lies a short drive off Montauk Highway, beyond the better-known village centers.
Quogue Wildlife Refuge, Quogue – The westernmost stop in this guide. Trails circle a pond and run out into a pocket of pine barrens, at a distance that suits younger legs and a first hike.
Elizabeth A. Morton National Wildlife Refuge, Noyac – One hundred eighty-seven acres in the Town of Southampton, taking in Jessup’s Neck, a peninsula about a mile and a half long separating Little Peconic Bay from Noyack Bay. Note before you go: the refuge asks visitors not to hand-feed the birds, reversing a long local habit. Seed left on the trail attracts pests that can harm wildlife and people. Parts of the beach close during nesting season, and dogs are not permitted.
Long Pond Greenbelt, Sag Harbor to Bridgehampton – A chain of coastal plain ponds running from Sag Harbor down toward the ocean. The habitat is genuinely rare, and the corridor is long enough to walk for hours.
Sagg Swamp Preserve, Sagaponack – A short boardwalk through red maple and sphagnum moss, and a quieter counterpoint to the beaches a few minutes south. From the 1600s into the 1800s this ground carried a series of short-lived gristmills, fulling mills, and even a brewery before it returned to swampland around 1850.
Cedar Point County Park, East Hampton – Trails lead toward views of Cedar Island Lighthouse across Gardiners Bay.
Local Tip: The South Fork preserves are at their best well after Labor Day. Long Pond Greenbelt in particular, once the crowds thin out and the swamp maples turn.
Montauk
Montauk has some of the East End’s longest and most varied trail networks. This is where a walk stops being a stroll.
Napeague Walking Dunes, Napeague – On the east side of Napeague Harbor, within Hither Hills State Park, three parabolic dunes rising to roughly eighty feet are migrating slowly southeast. They bury the forest as they go and uncover it again on the far side, leaving standing dead trees behind them. The landscape does not look like Long Island, and the trail rewards taking your time.
Hither Hills State Park, Montauk – One of the largest trail networks on the East End, running from the ocean beach up through Hither Woods to overlooks on Block Island Sound. A short walk turns into a long one without much warning, which is either the appeal or the thing to watch for.
Theodore Roosevelt County Park, Montauk – Rolling former ranchland with trails out to Big Reed Pond, a designated National Natural Landmark, and an observation deck looking over the water.
Shadmoor State Park, Montauk – A quick bluff-top walk above the Atlantic, with World War II observation bunkers still visible among the shadbush.
Camp Hero State Park, Montauk – Cliffside trails and maritime forest around the former military site, marked by its prominent Cold War radar tower.
Montauk Point State Park, Montauk – The end of the line. Trails run down to Money Pond and out along the shoreline, where you may spot harbor seals on the rocks through the colder months.
Local Tip: Camp Hero and Montauk Point sit right next to each other and are close enough to pair in a single outing. Check trail connections and parking before you go.
Make a Day of It, or Stay the Night
Three routes that pair a trail with somewhere to eat and somewhere to end up.
The Sound Day
Wildwood in the morning while your legs are fresh and the stairway is still a good idea. Hallock in the afternoon for the beach walk. Dinner in Riverhead or out along Sound Avenue in Jamesport.
The Ferry Day
Cross to Shelter Island early, spend the bulk of the day on the Mashomack trails, walk the Sylvester Manor grounds when your feet have had enough of the woods, and come back off the island through Greenport.
The Long Montauk Day
Start at the Walking Dunes before the wind picks up. Move into Hither Woods for the middle of the day. Finish at Montauk Point, which is the only ending this stretch of coast really allows.
Two of those three want an overnight, and all three are better with one. The Sound Day and the Montauk Day both run out of daylight before they run out of trail, and driving back west after a full day of walking is how good trips turn into long ones.
Where to Stay: Find places to stay across the East End
Before You Go
- Ticks are the single most important thing to plan for out here, in every season, not just summer. Long pants, repellent, and a real check when you get back to the car.
- Trail conditions change with storms and seasonal maintenance. Check the managing agency’s website before you drive out, since these preserves are run by five different bodies: New York State Parks, Suffolk County, the towns, the Nature Conservancy, and the US Fish and Wildlife Service.
- Parking rules are not consistent between them. Some sites require a town permit, some sell a day pass, and some restrict lots seasonally. Confirm on the site’s own page rather than assuming.
- Dog rules vary sharply. Elizabeth A. Morton National Wildlife Refuge does not allow pets, and Mashomack has restrictions. Check the managing organization’s current policy before bringing a dog.
- Hunting seasons affect access at some county and town properties in fall and winter.
- Most of these trails have no water, no facilities, and long stretches with no shade. Carry what you need.
- Stay on the marked path. Several of these places protect fragile dune, bog, and shoreline nesting habitat that a single set of footprints can damage.
The Shape Underneath
Drive the East End and it reads as a string of villages connected by two highways and a lot of farm stands. Walk it and the older shape comes through. The ridge of hills is glacial moraine. The ponds are kettle holes left where buried ice melted out. The bays sit where the ice stopped. The dunes at Napeague are still moving, a few inches a year, burying trees as they go.
These trails are not a scattered list of places to park. They are sections of one landscape, and a good stretch of it is stitched together on foot by a single white-blazed path that ends at a lighthouse.
Heading out to Montauk Point in the colder months? Our guide to whales, seals, and where to find them covers the haul-out season and the operators running trips.
Find your East End.