Forty hikes across the Hamptons, the North Fork, and Shelter Island — from state parks and preserves to town trails.
Walking a dog? Beach rules by town, plus every dog-friendly trail here
21 trails
Bridgehampton · 1 trail
Sagaponack · 1 trail
East Hampton · 7 trails
East Hampton · South Fork
3.5 mi · Moderate · Dirt · NY DEC
Woodland · Bay view · Salt marsh
Quiet woodland with a network of fire roads and footpaths ending at Barcelona Beach on Northwest Harbor. Bird-rich in spring and fall migration. The DEC-managed section connects to the town Northwest Path.
East Hampton · South Fork
5.2 mi · Moderate · Dirt · Town / Village park
Woodland · Bay view
Five miles of East Hampton Town trails through the Northwest Woods, ending at Northwest Harbor. Quiet even on summer weekends. Easy mountain biking; connects to Barcelona Neck at the north end.
East Hampton · South Fork
4 mi · Easy · Mixed · Suffolk County
Bay view · Historic · Woodland
Flat trail from the campground to the 1860 Cedar Point Lighthouse on Gardiners Bay. The lighthouse was on an island until the 1938 Hurricane filled in the channel. Great family walk with a clear destination.
East Hampton · South Fork
2 mi · Easy · Mixed · Town / Village park
Bay view · Woodland · Salt marsh
East Hampton town park on Gardiners Bay. Loop through pitch pine woods to a narrow beach on Three Mile Harbor. Kids, dogs, and a picnic at the end is the classic Sunday.
East Hampton · South Fork
1.1 mi · Easy · Sand · Town / Village park
Ocean view · Dunes
A short dune walk from the Two Mile Hollow lot out over the primary dune and down the beach. Dogs allowed off-leash before 9 a.m. and after 6 p.m. in summer. The locals' dog-walking beach.
East Hampton · South Fork
1.4 mi · Easy · Dirt · Suffolk County
Freshwater · Woodland
Short loop around a coastal plain pond in a Suffolk County nature preserve. Spring peepers in April, swamp azalea in May, and the rare Plymouth gentian in late summer.
East Hampton · South Fork
2.6 mi · Easy · Dirt · Town / Village park
Woodland
Quiet East Hampton town connector through oak-pine woods between Buckskill Road and Stephen Hands Path. Mostly flat, good for a fast dog walk or an easy mountain-bike loop.
Amagansett · 2 trails
Amagansett · South Fork
2.5 mi · Easy · Sand · Nature Conservancy
Dunes · Ocean view · Woodland
A Nature Conservancy preserve running between the primary and secondary dune lines. Beach plum, bayberry, prickly pear cactus, and migratory songbirds in spring. Boardwalk sections over the frailest dune faces.
Amagansett · South Fork
1.6 mi · Easy · Dirt · Town / Village park
Freshwater · Woodland
Small Amagansett preserve named for the historic cranberry bogs that once dotted Napeague. The loop passes a quiet pond and a pitch pine stand. Near-zero crowds.
Montauk · 6 trails
Montauk · South Fork
6.5 mi · Moderate · Dirt · NY State Parks
Woodland · Bay view · Ocean view
The long-distance trail of Long Island, 125 miles from Rocky Point east to Montauk Point. Most people day-hike a section, and the Hither Woods segment is the classic — oak and pine forest, kettle ponds, a ridge-line view over Napeague Harbor, the Atlantic on the south side.
Montauk · South Fork
6.5 mi · Moderate · Dirt · NY State Parks
Woodland · Bay view · Freshwater
Blue-blazed loop through oak and pitch pine, kettle ponds, and the Serpent's Back ridge. Flip-flopped clockwise gets the climb out of the way early. Deer, box turtles, and more ticks than you want — full pants are the move.
Montauk · South Fork
1.5 mi · Easy · Dirt · NY State Parks
Bluff · Ocean view · Historic
A short loop on the high bluffs east of Montauk village. World War II concrete bunkers sit right at the cliff edge. Fenced overlooks, Atlantic horizon, and a stair path down to Shadmoor Beach at low tide.
Montauk · South Fork
3.2 mi · Moderate · Dirt · NY State Parks
Bluff · Ocean view · Historic
Cold War radar base converted to state park. The SAGE radar tower still looms over the trail. Loop passes coastal gun batteries, oak scrub, and a bluff-edge view straight at the Montauk Lighthouse.
Montauk · South Fork
2 mi · Easy · Mixed · NY State Parks
Ocean view · Bluff · Historic
The easternmost tip of Long Island. Trail loops around the 1796 lighthouse, past Oyster Pond, and down to a pebble beach where harbor seals haul out in winter. This is where the Paumanok Path ends.
Montauk · South Fork
1.5 mi · Easy · Dirt · Suffolk County
Freshwater · Woodland
Quiet loop around a freshwater pond on the Montauk moors. Beavers, wood ducks, and a stand of hardwoods that burn gold in October. Part of the county's Third House Nature Center complex.
Sag Harbor · 1 trail
Sag Harbor · South Fork
6.5 mi · Moderate · Dirt · Town / Village park
Woodland · Freshwater
A 6.5-mile corridor of interconnected ponds from Sag Harbor south to Sagaponack, one of the largest contiguous coastal plain pond systems in the state. Rare sedges, globally uncommon plants, and a lot of quiet.
North Sea · 1 trail
Springs · 1 trail
Napeague · 1 trail
Napeague · South Fork
1 mi · Moderate · Sand · NY State Parks
Dunes · Bay view · Woodland
The famous migrating parabolic dunes on Napeague. Climb a 40-foot sand wall, walk the cranberry bog, pass the phantom forest where the advancing dune is slowly burying a stand of pitch pines. Best at low sun.
5 trails
Shelter Island · 5 trails
Shelter Island · Shelter Island
11 mi · Strenuous · Dirt · Nature Conservancy
Woodland · Salt marsh · Bay view
The long Red Trail is the full perimeter loop of Mashomack Preserve, about eleven miles through oak-beech forest, salt marsh, and tidal creeks. This is the big day out on Shelter Island. Plan on four to five hours.
Shelter Island · Shelter Island
6 mi · Moderate · Dirt · Nature Conservancy
Woodland · Salt marsh
The Yellow Trail is the middle Mashomack loop, six miles through oak forest to a salt-creek overlook at Bass Creek. Osprey platforms, box turtles, and a stand of enormous tupelo trees near the turnaround.
Shelter Island · Shelter Island
3 mi · Easy · Dirt · Nature Conservancy
Woodland · Freshwater
The Blue Trail is the shorter three-mile Mashomack loop, mostly flat oak woods with a kettle-pond overlook. A good introduction to the preserve when the kids can't do eleven miles.
Shelter Island · Shelter Island
1.5 mi · Easy · Dirt · Nature Conservancy
Woodland
The shortest Mashomack loop, 1.5 miles, entirely woodland. Start here if it's your first time, or do it with anyone who needs a flat, easy introduction to the preserve.
Shelter Island · Shelter Island
2.5 mi · Easy · Dirt · Nonprofit / Land trust
Historic · Woodland · Salt marsh
A 243-acre working historic farm on Shelter Island, the oldest surviving provisioning plantation in the northeastern US. The trail network crosses pasture, woodland, and a salt marsh, with interpretive signs about the Manhansett people and the 1652 manor house.
4 trails
Quogue · 1 trail
Hampton Bays · 1 trail
Westhampton · 1 trail
Wading River · 1 trail
10 trails
Riverhead · 2 trails
Riverhead · North Fork
4 mi · Moderate · Dirt · NY State Parks
Sound view · Bluff · Woodland
The newest state park on Long Island. 225 acres of oak forest, coastal ponds, and a bluff trail that drops to a quiet Long Island Sound beach. Kiosk and nature center at the lot. No swimming.
Riverhead · North Fork
2.8 mi · Easy · Mixed · Suffolk County
Bay view · Salt marsh · Woodland
A Peconic River estuary park where the river meets Flanders Bay. Flat loop with a view of the narrows, a campground, and a shoreline of reeds and osprey platforms.
Laurel · 1 trail
Cutchogue · 1 trail
Peconic · 2 trails
Peconic · North Fork
2.1 mi · Easy · Dirt · Suffolk County
Sound view · Bluff · Woodland
A Suffolk County park on the Long Island Sound bluffs. Woods trail loops down to a pebbly Sound beach. Traditionally the 4-H camp; quiet during the school year.
Peconic · North Fork
1.2 mi · Easy · Sand · Suffolk County
Sound view · Dunes
Short beach walk at the mouth of Goldsmith Inlet, a tidal pond on the Long Island Sound. Harbor seals in winter, osprey in summer, and a rarely crowded stretch of Sound beach.
Southold · 2 trails
Southold · North Fork
1.8 mi · Easy · Boardwalk · Town / Village park
Salt marsh · Woodland
Southold Town preserve with a boardwalk through a freshwater swamp and a short upland loop. Excellent spring migration birding. Quiet even in July.
Southold · North Fork
1.8 mi · Easy · Mixed · Town / Village park
Bay view · Salt marsh · Dunes
Southold town park at the tip of a narrow peninsula in Hog Neck Bay. Short trail through dune and salt marsh to a quiet bay beach. Osprey platform and a wide view across to Shelter Island.
Greenport · 1 trail
Orient · 1 trail
Lengths, difficulty, rules on dogs and bikes, and trailhead coordinates come from NY State Parks, Suffolk County Parks, NY DEC, The Nature Conservancy, Peconic Land Trust, US Fish & Wildlife, the NY–NJ Trail Conference, and town and village park departments, with trailhead coordinates cross-checked against OpenStreetMap.
Each trail page lists the specific official pages it was checked against, and each card above names the managing agency. Conditions change — confirm hours and access with the manager before a long drive.