Bridgehampton · South Fork
Wolf Swamp Preserve
1.8 mi · Easy · Dirt · Peconic Land Trust
Woodland · Freshwater
Peconic Land Trust preserve of oak-hickory woods and a quiet swamp.
Trails & Hikes
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
Filters40 trails
- South Fork
- North Fork
- Shelter Island
21 trails
Bridgehampton · 1 trail
Sagaponack · 1 trail
East Hampton · 7 trails
East Hampton · South Fork
Barcelona Neck
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.
East Hampton · South Fork
Northwest Path
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.
East Hampton · South Fork
Cedar Point County Park — Lighthouse Trail
4 mi · Easy · Mixed · Suffolk County
Bay view · Historic · Woodland
Flat trail from the campground to the 1860 Cedar Point Lighthouse on Gardiners Bay.
East Hampton · South Fork
Maidstone Park Trails
2 mi · Easy · Mixed · Town / Village park
Bay view · Woodland · Salt marsh
East Hampton town park on Gardiners Bay.
East Hampton · South Fork
Two Mile Hollow Beach Trail
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.
East Hampton · South Fork
Munns Pond County Park
1.4 mi · Easy · Dirt · Suffolk County
Freshwater · Woodland
Short loop around a coastal plain pond in a Suffolk County nature preserve.
Show 32 more trails
East Hampton · 7 trails
Amagansett · 2 trails
Amagansett · South Fork
Atlantic Double Dunes Preserve
2.5 mi · Easy · Sand · Nature Conservancy
Dunes · Ocean view · Woodland
A Nature Conservancy preserve running between the primary and secondary dune lines.
Amagansett · South Fork
Cranberry Hole Preserve
1.6 mi · Easy · Dirt · Town / Village park
Freshwater · Woodland
Small Amagansett preserve named for the historic cranberry bogs that once dotted Napeague.
Montauk · 6 trails
Montauk · South Fork
Paumanok Path (Hither Woods section)
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.
DanTD / Wikimedia Commons (CC BY-SA 4.0) Montauk · South Fork
Hither Woods Loop
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.
Montauk · South Fork
Shadmoor State Park Bluff Trail
1.5 mi · Easy · Dirt · NY State Parks
Bluff · Ocean view · Historic
A short loop on the high bluffs east of Montauk village.
Montauk · South Fork
Camp Hero — Battery Osborne Loop
3.2 mi · Moderate · Dirt · NY State Parks
Bluff · Ocean view · Historic
Cold War radar base converted to state park.
Montauk · South Fork
Montauk Point State Park Trails
2 mi · Easy · Mixed · NY State Parks
Ocean view · Bluff · Historic
The easternmost tip of Long Island.
Montauk · 6 trails
Sag Harbor · 1 trail
Americasroof at English Wikipedia / Wikimedia Commons (CC BY-SA 3.0) Sag Harbor · South Fork
Long Pond Greenbelt
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…
North Sea · 1 trail
Springs · 1 trail
Napeague · 1 trail
5 trails
Shelter Island · 5 trails
Shelter Island · Shelter Island
Mashomack Preserve — Red Trail
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…
Shelter Island · Shelter Island
Mashomack Preserve — Yellow Trail
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.
Shelter Island · Shelter Island
Mashomack Preserve — Blue Trail
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.
Shelter Island · 5 trails
Shelter Island · Shelter Island
Mashomack Preserve — Green Trail
1.5 mi · Easy · Dirt · Nature Conservancy
Woodland
The shortest Mashomack loop, 1.5 miles, entirely woodland.
Shelter Island · Shelter Island
Sylvester Manor Educational Farm
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.
3 trails
Quogue · 1 trail
Hampton Bays · 1 trail
Westhampton · 1 trail
11 trails
Wading River · 1 trail
Riverhead · 2 trails
EBCarrier / Wikimedia Commons (CC BY-SA 4.0) Riverhead · North Fork
Hallock State Park Preserve
4 mi · Moderate · Dirt · NY State Parks
Sound view · Bluff · Woodland
The newest state park on Long Island.
Riverhead · North Fork
Indian Island County Park — Peconic River Trails
2.8 mi · Easy · Mixed · Suffolk County
Bay view · Salt marsh · Woodland
A Peconic River estuary park where the river meets Flanders Bay.
Laurel · 1 trail
Cutchogue · 1 trail
Peconic · 2 trails
Peconic · North Fork
Peconic Dunes County Park
2.1 mi · Easy · Dirt · Suffolk County
Sound view · Bluff · Woodland
A Suffolk County park on the Long Island Sound bluffs.
Peconic · North Fork
Goldsmith Inlet County Park
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.
Southold · 2 trails
Southold · North Fork
Arshamomaque Preserve
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.
Southold · North Fork
Cedar Beach Point Trails
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.
Greenport · 1 trail
Orient · 1 trail
Where this information comes from
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.