Fairfield Trails and Maps

Looking for the best trails around Fairfield?

Find the top rated trails in Fairfield, whether you're looking an easy walking path or a long bike trail, you'll find what you're looking for. Click on a trail below to find trail descriptions, trail maps, photos, and reviews.

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  • Length
Activities
Length
Surfaces
Type
62 Results
Activities
Length
Surfaces
Type

Air Line State Park Trail

55.9 mi
State: CT
Gravel

Beach Channel Drive Greenway

1 mi
State: NY
Asphalt

Bethpage Bikeway

12.5 mi
State: NY
Asphalt

Branford Trolley Trail

0.5 mi
State: CT
Concrete, Crushed Stone, Gravel

Briarcliff-Peekskill Trailway

12 mi
State: NY
Asphalt, Dirt, Grass

Bronx River Greenway

18.1 mi
State: NY
Asphalt, Concrete, Dirt

CTfastrak Multi-Use Trail

4.4 mi
State: CT
Asphalt, Concrete

Cross Island Parkway Trail

3.1 mi
State: NY
Asphalt

Derby Greenway

1.85 mi
State: CT
Asphalt

East River Greenway

9.4 mi
State: NY
Asphalt

Eastern Parkway Trail

2 mi
State: NY
Asphalt, Concrete

Farmington Canal Heritage Trail

40 mi
State: CT
Asphalt, Cinder, Crushed Stone, Grass, Gravel

Farmington River Trail

14.9 mi
State: CT
Asphalt, Cinder, Crushed Stone, Dirt

Harlem Valley Rail Trail

17.3 mi
State: NY
Asphalt, Crushed Stone

High Line

1.5 mi
State: NY
Concrete

Hook Mountain/Nyack Beach Bikeway

4.9 mi
State: NY
Asphalt, Ballast, Crushed Stone, Dirt, Gravel

Hudson River Greenway

11 mi
State: NY
Asphalt, Concrete

Hudson River Waterfront Walkway

1.5 mi
State: NJ
Concrete
Accordion

Hutchinson River Greenway

2.2 mi
State: NY
Asphalt, Concrete

Jack Harrington White Plains Greenway

1.2 mi
State: NY
Woodchips

John Kieran Nature Trail

1 mi
State: NY
Dirt, Gravel, Woodchips

Jones Point Path

2 mi
State: NY
Ballast, Dirt

Joseph B. Clarke Rail Trail

2.8 mi
State: NY
Asphalt, Crushed Stone, Dirt, Gravel

Kennedy Trail

1.7 mi
State: NY
Cinder

Kings Park Hike & Bike Trail

1.5 mi
State: NY
Asphalt

Klara Sauer Trail

1 mi
State: NY
Crushed Stone

Kress Family Trail

2.5 mi
State: CT
Dirt

Larkin State Park Trail

10.4 mi
State: CT
Cinder, Crushed Stone, Dirt, Gravel

Maybrook Trailway

3.7 mi
State: NY
Asphalt

Middlebury Greenway

4.4 mi
State: CT
Asphalt

Mosholu-Pelham Greenway

10.3 mi
State: NY
Asphalt

Naugatuck River Greenway

5.4 mi
State: CT
Asphalt

New Milford River Trail

5 mi
State: CT
Asphalt, Crushed Stone, Dirt

North County Trailway

22.1 mi
State: NY
Asphalt

Norwalk River Valley Trail

5.8 mi
State: CT
Asphalt

Ocean Parkway Coastal Greenway

3.6 mi
State: NY
Asphalt

Old Croton Aqueduct Trail

22.8 mi
State: NY
Asphalt, Concrete, Dirt

Old Erie Path

3 mi
State: NY
Ballast, Crushed Stone, Dirt, Grass, Gravel

Old Mine Railroad Trail

2.2 mi
State: NY
Dirt

Old Putnam Trail

1.25 mi
State: NY
Cinder, Dirt, Grass

Pequonnock River Trail

12.8 mi
State: CT
Asphalt, Crushed Stone

Putnam Trailway

11.55 mi
State: NY
Asphalt

Quarry Trail

0.1 mi
State: NY
Dirt, Grass

Ramsey Bike Path

1 mi
State: NJ
Asphalt

Raymond G. Esposito Trail

1 mi
State: NY
Crushed Stone, Dirt, Gravel

Ridgefield Rail Trail

2.3 mi
State: CT
Gravel

Roosevelt Island Greenway

3.8 mi
State: NY
Asphalt

Samuel G. Fisher Mount Ivy Environmental Park

2 mi
State: NY
Ballast, Cinder, Dirt, Grass, Woodchips

Savin Rock Trail

1.2 mi
State: CT
Asphalt, Concrete

Shore Parkway Greenway Trail

12.4 mi
State: NY
Asphalt, Concrete

Shoreline Greenway Trail

2.3 mi
State: CT
Crushed Stone

South County Trailway

14.7 mi
State: NY
Asphalt, Concrete

Sue Grossman Still River Greenway

2.9 mi
State: CT
Asphalt

Tallman Mountain State Park Bike Path

2.1 mi
State: NY
Asphalt, Cinder, Dirt

Timp-Torne Trail

5.4 mi
State: NY
Dirt

Vanderbilt Motor Parkway

3 mi
State: NY
Asphalt
Trail Image Trail Name States Length Surface Rating
Air Line State Park Trail winds for just over 55 miles from the northeast corner of Connecticut, where the state borders Massachusetts, down to East Hampton in the heart of the state. Over the state...
CT 55.9 mi Gravel
Although just a mile long, the Beach Channel Drive Greenway in Queens offers expansive views of Jamaica Bay and the beautiful Marine Parkway Bridge as it traces the border of Jacob Riis Park. On the...
NY 1 mi Asphalt
The Bethpage Bikeway is one of Long Island's most popular trails. It connects Merrick Road in Massapequa with Bethpage State Park, and includes additional trail north to Trail View State Park in...
NY 12.5 mi Asphalt
The Branford Trolley Trail is essentially a long footbridge occupying an old bridge along the route of an abandoned trolley track. The bridge links nature trails on both sides of the water through a...
CT 0.5 mi Concrete, Crushed Stone, Gravel
The Briarcliff-Peekskill Trailway is a 12-mile linear park that runs from the town of Ossining north to Westchester County's Blue Mountain Reservation in Peekskill. The trail is built on land...
NY 12 mi Asphalt, Dirt, Grass
The Bronx River Greenway will one day stretch 23 miles along the river through New York's Westchester and Bronx counties. Currently, 18 miles of the trail are complete in disconnected segments largely...
NY 18.1 mi Asphalt, Concrete, Dirt
A part of Connecticut's first bus rapid transit line, the CTfastrak Trail serves as recreational and multi-use path for walking and bicycling between Downtown New Britain and Newington Junction. The...
CT 4.4 mi Asphalt, Concrete
The Cross Island Parkway Trail closely follows its namesake thoroughfare through northeastern Queens. From its northern end, you will soon enter Little Bay Park, which offers lovely views of the...
NY 3.1 mi Asphalt
The Derby Greenway runs between Division Street and Main Street, paralleling the Naugatuck and Housatonic rivers. The trail runs on top of a flood control dyke for the rivers; a portion of it goes...
CT 1.85 mi Asphalt
The EPCAL Alternative Transportation Path loops around the 2,900-acre Enterprise Park at Calverton (hence its name: EPCAL) on New York’s Long Island and links to the Town of Riverhead’s 65-acre...
NY 8.5 mi Asphalt
New York City's East River Greenway offers views of the East River, Queens, Brooklyn, and the iconic bridges that connect these boroughs to Manhattan. The paved pathway traces the waterfront on one...
NY 9.4 mi Asphalt
The Eastern Parkway Trail is a 2-mile route along a tree-lined boulevard in Brooklyn's Crown Heights neighborhood. The path begins at Prospect Park, which houses some of Brooklyn's most popular...
NY 2 mi Asphalt, Concrete
Running north from the Yale University campus in New Haven through the heart of Connecticut, the multi-use Farmington Canal Heritage Trail, when completed will stretch uninterrupted more than 80 miles...
CT 40 mi Asphalt, Cinder, Crushed Stone, Grass, Gravel
The Farmington River Trail is built upon the former Central New England Railroad corridor and runs between the Farmington Canal Heritage Trail near Tunxis Meade Park and the Simsbury town line. A...
CT 14.9 mi Asphalt, Cinder, Crushed Stone, Dirt
Harlem Valley Rail Trail provides a scenic ride through rolling farm fields and dense woods on the bed of the New York and Harlem Railroad that ran from New York City to Chatham. The rail-trail is...
NY 17.3 mi Asphalt, Crushed Stone
Much of the 15-mile Heritage Trail, a.k.a. the Orange Heritage Trail, sails past wide fields of corn and wheat. The trail starts in Harriman at the Mary Harriman Park. From there, it heads northwest...
NY 15 mi Asphalt
The High Line rail-trail is an urban marvel, stretching 1.5 miles and towering almost 30 feet above street level through several neighborhoods in the lower west side of Manhattan. The first section...
NY 1.5 mi Concrete
While not a "rail-trail," the Hook Mountain/Nyack Beach Bikeway is a very scenic trail along the Hudson River in Rockland County. The southern half of this trail is flat and runs right along the...
NY 4.9 mi Asphalt, Ballast, Crushed Stone, Dirt, Gravel
Hudson River Greenway provides a continuous 11-mile route between Battery Park at the southern tip of Manhattan and the Little Red Lighthouse underneath the George Washington Bridge. The trail passes...
NY 11 mi Asphalt, Concrete
The Hudson River Waterfront Walkway is a 1.5 mile walkway along the bank of the Hudson River in Jersey City. The walkway offers stunning views of Manhattan as well as access to a number of ferries and...
NJ 1.5 mi Concrete
Accordion
The Hutchinson River Greenway offers a convenient alternative to the Hutchinson River Parkway, which it closely follows. Although adjacent to the busy thoroughfare, trees have been planted along the...
NY 2.2 mi Asphalt, Concrete
The Jack Harrington White Plains Greenway was recently renamed to honor a long-time member of the city's conservation board. The trail's corridor follows the former New York, Westchester & Boston...
NY 1.2 mi Woodchips
The John Kieran Nature Trail is a short loop that borders Van Cortlandt Lake and its associated wetlands. It is a wonderful site for bird-watching. The trail also passes several sites of significance...
NY 1 mi Dirt, Gravel, Woodchips
Jones Beach Bikeway is a paved bicycle and pedestrian path on the southwestern end of Long Island that parallels Wantagh Parkway from Seaford to Jones Beach State Park. The trail is also known by two...
NY 5.3 mi Asphalt
The Jones Point Path occupies an abandoned motor vehicle route (old US Route 9W). The path provides bicyclists with a relatively safe bypass to a dangerous section of busy US Route 9W near Bear...
NY 2 mi Ballast, Dirt
These three contiguous trails—the Raymond G. Esposito Memorial Trail, Old Erie Path and Joseph B. Clarke Trail—occupy the former right-of-way of the Erie Railroad's Nyack and Piermont Branch. Each...
NY 2.8 mi Asphalt, Crushed Stone, Dirt, Gravel
The Kennedy Trail begins at the northwest corner of the 68-acre campus of John F. Kennedy Catholic High School in Somers. The town, which sits 30 miles from White Plains and 55 miles from New York...
NY 1.7 mi Cinder
The Kings Park Hike & Bike Trail runs for 1.5 miles between Old Dock Road at Church Street in Kings Park and Nissequogue River State Park. The trail is a town of Smithtown park and follows an...
NY 1.5 mi Asphalt
The Klara Sauer Trail (formerly known as the Beacon Riverside Trail) runs for 1 mile along the Hudson River on the west side of New York's village of Beacon. The trail occupies the same corridor as...
NY 1 mi Crushed Stone
The Kress Family Trail follows an old rail bed of the former Shepaug Railroad, which winds along the Shepaug River. The flat, 2.5-mile trail is popular with cross-country skiers and snowshoers in...
CT 2.5 mi Dirt
Canopied with deciduous trees for most of its 10.4 miles, the Larkin State Park Trail (a.k.a. Larkin Bridle Path) is primarily a wilderness trail, with wooded vistas, wetland views and sparse...
CT 10.4 mi Cinder, Crushed Stone, Dirt, Gravel
Owned by the Metro-North Railroad, the Maybrook Trailway starts at the Connecticut state line in Farringtons Park, and spans 5 miles into the town of Brewster. The trail follows what was once part of...
NY 3.7 mi Asphalt
The delightful asphalt Middlebury Greenway winds 4.4 miles through the residential community of Middlebury, connecting businesses, parks and neighborhoods. The popular trail offers residents an...
CT 4.4 mi Asphalt
The Mosholu-Pelham Greenway connects several parks and recreational opportunities in New York City's north and central Bronx neighborhoods. A portion of the trail is also part of the growing East...
NY 10.3 mi Asphalt
The Naugatuck River Greenway will one day span 44 miles from Torrington to Derby in western Connecticut, but is currently open in a few short disconnected segments totaling just over 5 miles. The...
CT 5.4 mi Asphalt
The first phase of the New Milford River Trail runs southeast from Gaylordsville via the scenic but lightly traveled River Road, through Sega Meadows to Boardman Bridge, a distance of about 5 miles....
CT 5 mi Asphalt, Crushed Stone, Dirt
The North County Trailway is the longest of the four connected rail-trails breathing new life into the former New York Central Railroad's Putnam Division line. The "Old Put" provided passenger and...
NY 22.1 mi Asphalt
When completed, the Norwalk River Valley Trail will run from Danbury to Long Island Sound in southwestern Connecticut, for a total of about 27 miles. Currently, several disconnected sections totaling...
CT 5.8 mi Asphalt
Ocean Parkway Coastal Greenway, which opened in June 2014, runs just shy of 4 miles between Jones Beach State Park and Tobay Beach. Both beaches permit swimming and provide opportunities to purchase...
NY 3.6 mi Asphalt
The Old Croton Aqueduct State Historic Park follows the route of the Old Croton Aqueduct, which carried water to New York City from 1842 to 1955. Most of the structure lies beneath the trail and has...
NY 22.8 mi Asphalt, Concrete, Dirt
These three contiguous trails—the Raymond G. Esposito Memorial Trail, Old Erie Path and Joseph B. Clark Trail—occupy the former right-of-way of the Erie Railroad's Nyack and Piermont Branch. Each...
NY 3 mi Ballast, Crushed Stone, Dirt, Grass, Gravel
Fahnestock State Park is a relatively undiscovered gems in the New York State Park System. Located a few miles east of Cold Spring Village on Rt. 301 (Main Street), the park jurisdiction was recently...
NY 2.2 mi Dirt
Splayed over 1,146 acres in northwest Bronx, Van Cortlandt Park has a lot going on. The park is New York City's fourth largest and is home to the oldest municipal golf course in America. There are...
NY 1.25 mi Cinder, Dirt, Grass
The Pequonnock River Trail—portions of which are also known as the Housatonic Railway Rails to Trails, Monroe Housatonic Railbed Trail and Pequonnock Valley Greenway—is a developing system stretching...
CT 12.8 mi Asphalt, Crushed Stone
The final passenger cars of the Putnam Division of the New York Central Railroad ran in 1958, but the rail line that so influenced development of this area still sparks nostalgia. The "Old Put"...
NY 11.55 mi Asphalt
The Quarry Trail is currently a 600-foot long unimproved strip of land along what is known as Quarry Road in the Village of Hastings-on-Hudson, NY. The trail links Old Croton Aqueduct State Historic...
NY 0.1 mi Dirt, Grass
The Ramsey Bike Path is a recreational path built on the former Paterson to Suffern trolley line right-of-way. The path extends along a north-south route from one end of Ramsey to the other....
NJ 1 mi Asphalt
These three contiguous trails—the Raymond G. Esposito Memorial Trail, Old Erie Path and Joseph B. Clark Trail—occupy the former right-of-way of the Erie Railroad's Nyack and Piermont Branch. Each...
NY 1 mi Crushed Stone, Dirt, Gravel
The Ridgefield Rail-Trail meanders for nearly 2.5 miles through the forested exburbs of Ridgefield, Connecticut. The trail passes among suburban acreages, along a creek at one point, and past a couple...
CT 2.3 mi Gravel
Roosevelt Island Greenway, a little-known gem in the Big Apple, was named after President Franklin Delano Roosevelt in 1973. To reach this scenic pathway, board New York City’s only aerial tram,...
NY 3.8 mi Asphalt
The Saddle River Area Bike Path in Bergen County stretches for nearly 6 miles along a 577-acre linear park system that hugs the banks of the Saddle River and its tributaries. There are actually five...
NJ 7.5 mi Asphalt
A former right-of-way of the NY & NJ Railroad. Near historical Mount Ivy which was the center of a Quaker settlement in the 18th century. Hiking along railroad bed and wildlife observation and...
NY 2 mi Ballast, Cinder, Dirt, Grass, Woodchips
The Savin Rock Trail offers just over a mile of paved pathway along West Haven’s coastline. Along the way, you’ll enjoy picturesque views of Long Island Sound and access to its sandy beaches. The west...
CT 1.2 mi Asphalt, Concrete
The Setauket-Port Jefferson Station Greenway Trail stretches just over 3 miles along Long Island’s north shore. Construction was completed in two phases with the first trail section opening in 2009...
NY 3.4 mi Asphalt
The Shore Parkway Greenway Trail is comprised of two disconnected segments along the New York Harbor that together offer more than 12 miles of paved pathway on Brooklyn's southern border. Between the...
NY 12.4 mi Asphalt, Concrete
When complete, Connecticut's Shoreline Greenway Trail will be a scenic 25-mile route through four quaint New England towns off Long Island Sound. From Lighthouse Point to Hammonasset Beach State Park,...
CT 2.3 mi Crushed Stone
The South County Trailway is a zippy paved trail heading north from Yonkers through the Hudson River Valley communities of Hastings-on-Hudson, Dobbs Ferry, Ardsley, Irvington, Greenburgh, and...
NY 14.7 mi Asphalt, Concrete
The Sue Grossman Still River Greenway runs for nearly 3 miles through a wooded corridor between Lanson Drive and Harris Drive in Torrington. The paved trail occupies the old right-of-way for the New...
CT 2.9 mi Asphalt
Tallman Mountain State Park Bike Path is partially paved and bisects the Tallman Mountain State Park. The route provides a motor-vehicle-free way for bicyclists using US Route 9W to connect with...
NY 2.1 mi Asphalt, Cinder, Dirt
Just an hour north of New York City, the Timp-Torne Trail offers a scenic hike through Bear Mountain and Harriman State Parks with panoramic vistas of the Hudson River. The rugged blue-blazed trail...
NY 5.4 mi Dirt

This trail is the legacy of the first elevated roadway in the United States, constructed by William K. Vanderbilt in 1904. Vanderbilt created the parkway to get to his family’s estate in Long...

NY 3 mi Asphalt
The Dutchess Rail Trail is a local treasure in the Hudson Valley region of New York, and for good reason: the 13-mile trail runs through what seems like a perpetually green landscape of dense tree...
NY 13 mi Asphalt

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Trails by activity

Ramsey Bike Path

NJ - 1 miles

The Ramsey Bike Path is a recreational path built on the former Paterson to Suffern trolley line right-of-way. The path extends along a north-south route from one end of Ramsey to the other....

Roosevelt Island Greenway

NY - 3.8 miles

Roosevelt Island Greenway, a little-known gem in the Big Apple, was named after President Franklin Delano Roosevelt in 1973. To reach this scenic pathway, board New York City’s only aerial tram,...

Beach Channel Drive Greenway

NY - 1 miles

Although just a mile long, the Beach Channel Drive Greenway in Queens offers expansive views of Jamaica Bay and the beautiful Marine Parkway Bridge as it traces the border of Jacob Riis Park. On the...

Setauket-Port Jefferson Station Greenway Trail

NY - 3.4 miles

The Setauket-Port Jefferson Station Greenway Trail stretches just over 3 miles along Long Island’s north shore. Construction was completed in two phases with the first trail section opening in 2009...

Accordion

William R. Steinhaus Dutchess Rail Trail

NY - 13 miles

The Dutchess Rail Trail is a local treasure in the Hudson Valley region of New York, and for good reason: the 13-mile trail runs through what seems like a perpetually green landscape of dense tree...

Saddle River Area Bike Path - Bergen County

NJ - 7.5 miles

The Saddle River Area Bike Path in Bergen County stretches for nearly 6 miles along a 577-acre linear park system that hugs the banks of the Saddle River and its tributaries. There are actually five...

Harlem Valley Rail Trail

NY - 17.3 miles

Harlem Valley Rail Trail provides a scenic ride through rolling farm fields and dense woods on the bed of the New York and Harlem Railroad that ran from New York City to Chatham. The rail-trail is...

Shore Parkway Greenway Trail

NY - 12.4 miles

The Shore Parkway Greenway Trail is comprised of two disconnected segments along the New York Harbor that together offer more than 12 miles of paved pathway on Brooklyn's southern border. Between the...

Bronx River Greenway

NY - 18.1 miles

The Bronx River Greenway will one day stretch 23 miles along the river through New York's Westchester and Bronx counties. Currently, 18 miles of the trail are complete in disconnected segments largely...

Ocean Parkway Coastal Greenway

NY - 3.6 miles

Ocean Parkway Coastal Greenway, which opened in June 2014, runs just shy of 4 miles between Jones Beach State Park and Tobay Beach. Both beaches permit swimming and provide opportunities to purchase...

Joseph B. Clarke Rail Trail

NY - 2.8 miles

These three contiguous trails—the Raymond G. Esposito Memorial Trail, Old Erie Path and Joseph B. Clarke Trail—occupy the former right-of-way of the Erie Railroad's Nyack and Piermont Branch. Each...

Mosholu-Pelham Greenway

NY - 10.3 miles

The Mosholu-Pelham Greenway connects several parks and recreational opportunities in New York City's north and central Bronx neighborhoods. A portion of the trail is also part of the growing East...

Norwalk River Valley Trail

CT - 5.8 miles

When completed, the Norwalk River Valley Trail will run from Danbury to Long Island Sound in southwestern Connecticut, for a total of about 27 miles. Currently, several disconnected sections totaling...

Hook Mountain/Nyack Beach Bikeway

NY - 4.9 miles

While not a "rail-trail," the Hook Mountain/Nyack Beach Bikeway is a very scenic trail along the Hudson River in Rockland County. The southern half of this trail is flat and runs right along the...

Naugatuck River Greenway

CT - 5.4 miles

The Naugatuck River Greenway will one day span 44 miles from Torrington to Derby in western Connecticut, but is currently open in a few short disconnected segments totaling just over 5 miles. The...

Air Line State Park Trail

CT - 55.9 miles

Air Line State Park Trail winds for just over 55 miles from the northeast corner of Connecticut, where the state borders Massachusetts, down to East Hampton in the heart of the state. Over the state...

New Milford River Trail

CT - 5 miles

The first phase of the New Milford River Trail runs southeast from Gaylordsville via the scenic but lightly traveled River Road, through Sega Meadows to Boardman Bridge, a distance of about 5 miles....

Bethpage Bikeway

NY - 12.5 miles

The Bethpage Bikeway is one of Long Island's most popular trails. It connects Merrick Road in Massapequa with Bethpage State Park, and includes additional trail north to Trail View State Park in...

Shoreline Greenway Trail

CT - 2.3 miles

When complete, Connecticut's Shoreline Greenway Trail will be a scenic 25-mile route through four quaint New England towns off Long Island Sound. From Lighthouse Point to Hammonasset Beach State Park,...

Old Erie Path

NY - 3 miles

These three contiguous trails—the Raymond G. Esposito Memorial Trail, Old Erie Path and Joseph B. Clark Trail—occupy the former right-of-way of the Erie Railroad's Nyack and Piermont Branch. Each...

John Kieran Nature Trail

NY - 1 miles

The John Kieran Nature Trail is a short loop that borders Van Cortlandt Lake and its associated wetlands. It is a wonderful site for bird-watching. The trail also passes several sites of significance...

Hutchinson River Greenway

NY - 2.2 miles

The Hutchinson River Greenway offers a convenient alternative to the Hutchinson River Parkway, which it closely follows. Although adjacent to the busy thoroughfare, trees have been planted along the...

EPCAL Alternative Transportation Path

NY - 8.5 miles

The EPCAL Alternative Transportation Path loops around the 2,900-acre Enterprise Park at Calverton (hence its name: EPCAL) on New York’s Long Island and links to the Town of Riverhead’s 65-acre...

Beach Channel Drive Greenway

NY - 1 miles

Although just a mile long, the Beach Channel Drive Greenway in Queens offers expansive views of Jamaica Bay and the beautiful Marine Parkway Bridge as it traces the border of Jacob Riis Park. On the...

Accordion

Kress Family Trail

CT - 2.5 miles

The Kress Family Trail follows an old rail bed of the former Shepaug Railroad, which winds along the Shepaug River. The flat, 2.5-mile trail is popular with cross-country skiers and snowshoers in...

Kennedy Trail

NY - 1.7 miles

The Kennedy Trail begins at the northwest corner of the 68-acre campus of John F. Kennedy Catholic High School in Somers. The town, which sits 30 miles from White Plains and 55 miles from New York...

Jones Beach Bikeway (Ellen Farrant Memorial Bikeway)

NY - 5.3 miles

Jones Beach Bikeway is a paved bicycle and pedestrian path on the southwestern end of Long Island that parallels Wantagh Parkway from Seaford to Jones Beach State Park. The trail is also known by two...

Hook Mountain/Nyack Beach Bikeway

NY - 4.9 miles

While not a "rail-trail," the Hook Mountain/Nyack Beach Bikeway is a very scenic trail along the Hudson River in Rockland County. The southern half of this trail is flat and runs right along the...

Cross Island Parkway Trail

NY - 3.1 miles

The Cross Island Parkway Trail closely follows its namesake thoroughfare through northeastern Queens. From its northern end, you will soon enter Little Bay Park, which offers lovely views of the...

Eastern Parkway Trail

NY - 2 miles

The Eastern Parkway Trail is a 2-mile route along a tree-lined boulevard in Brooklyn's Crown Heights neighborhood. The path begins at Prospect Park, which houses some of Brooklyn's most popular...

Shore Parkway Greenway Trail

NY - 12.4 miles

The Shore Parkway Greenway Trail is comprised of two disconnected segments along the New York Harbor that together offer more than 12 miles of paved pathway on Brooklyn's southern border. Between the...

Maybrook Trailway

NY - 3.7 miles

Owned by the Metro-North Railroad, the Maybrook Trailway starts at the Connecticut state line in Farringtons Park, and spans 5 miles into the town of Brewster. The trail follows what was once part of...

Roosevelt Island Greenway

NY - 3.8 miles

Roosevelt Island Greenway, a little-known gem in the Big Apple, was named after President Franklin Delano Roosevelt in 1973. To reach this scenic pathway, board New York City’s only aerial tram,...

Ocean Parkway Coastal Greenway

NY - 3.6 miles

Ocean Parkway Coastal Greenway, which opened in June 2014, runs just shy of 4 miles between Jones Beach State Park and Tobay Beach. Both beaches permit swimming and provide opportunities to purchase...

Farmington Canal Heritage Trail

CT - 40 miles

Running north from the Yale University campus in New Haven through the heart of Connecticut, the multi-use Farmington Canal Heritage Trail, when completed will stretch uninterrupted more than 80 miles...

Norwalk River Valley Trail

CT - 5.8 miles

When completed, the Norwalk River Valley Trail will run from Danbury to Long Island Sound in southwestern Connecticut, for a total of about 27 miles. Currently, several disconnected sections totaling...

Naugatuck River Greenway

CT - 5.4 miles

The Naugatuck River Greenway will one day span 44 miles from Torrington to Derby in western Connecticut, but is currently open in a few short disconnected segments totaling just over 5 miles. The...

Hudson River Greenway

NY - 11 miles

Hudson River Greenway provides a continuous 11-mile route between Battery Park at the southern tip of Manhattan and the Little Red Lighthouse underneath the George Washington Bridge. The trail passes...

Savin Rock Trail

CT - 1.2 miles

The Savin Rock Trail offers just over a mile of paved pathway along West Haven’s coastline. Along the way, you’ll enjoy picturesque views of Long Island Sound and access to its sandy beaches. The west...

Branford Trolley Trail

CT - 0.5 miles

The Branford Trolley Trail is essentially a long footbridge occupying an old bridge along the route of an abandoned trolley track. The bridge links nature trails on both sides of the water through a...

Heritage Trail (aka Orange Heritage Trail)

NY - 15 miles

Much of the 15-mile Heritage Trail, a.k.a. the Orange Heritage Trail, sails past wide fields of corn and wheat. The trail starts in Harriman at the Mary Harriman Park. From there, it heads northwest...

Briarcliff-Peekskill Trailway

NY - 12 miles

The Briarcliff-Peekskill Trailway is a 12-mile linear park that runs from the town of Ossining north to Westchester County's Blue Mountain Reservation in Peekskill. The trail is built on land...

Roosevelt Island Greenway

NY - 3.8 miles

Roosevelt Island Greenway, a little-known gem in the Big Apple, was named after President Franklin Delano Roosevelt in 1973. To reach this scenic pathway, board New York City’s only aerial tram,...

Hudson River Waterfront Walkway

NJ - 1.5 miles

The Hudson River Waterfront Walkway is a 1.5 mile walkway along the bank of the Hudson River in Jersey City. The walkway offers stunning views of Manhattan as well as access to a number of ferries and...

Accordion

Tallman Mountain State Park Bike Path

NY - 2.1 miles

Tallman Mountain State Park Bike Path is partially paved and bisects the Tallman Mountain State Park. The route provides a motor-vehicle-free way for bicyclists using US Route 9W to connect with...

North County Trailway

NY - 22.1 miles

The North County Trailway is the longest of the four connected rail-trails breathing new life into the former New York Central Railroad's Putnam Division line. The "Old Put" provided passenger and...

Branford Trolley Trail

CT - 0.5 miles

The Branford Trolley Trail is essentially a long footbridge occupying an old bridge along the route of an abandoned trolley track. The bridge links nature trails on both sides of the water through a...

Vanderbilt Motor Parkway

NY - 3 miles

<p>This trail is the legacy of the first elevated roadway in the United States, constructed by William K. Vanderbilt in 1904. Vanderbilt created the parkway to get to his family&rsquo;s estate in Long...

Ramsey Bike Path

NJ - 1 miles

The Ramsey Bike Path is a recreational path built on the former Paterson to Suffern trolley line right-of-way. The path extends along a north-south route from one end of Ramsey to the other....

Maybrook Trailway

NY - 3.7 miles

Owned by the Metro-North Railroad, the Maybrook Trailway starts at the Connecticut state line in Farringtons Park, and spans 5 miles into the town of Brewster. The trail follows what was once part of...

Air Line State Park Trail

CT - 55.9 miles

Air Line State Park Trail winds for just over 55 miles from the northeast corner of Connecticut, where the state borders Massachusetts, down to East Hampton in the heart of the state. Over the state...

Old Mine Railroad Trail

NY - 2.2 miles

Fahnestock State Park is a relatively undiscovered gems in the New York State Park System. Located a few miles east of Cold Spring Village on Rt. 301 (Main Street), the park jurisdiction was recently...

Kennedy Trail

NY - 1.7 miles

The Kennedy Trail begins at the northwest corner of the 68-acre campus of John F. Kennedy Catholic High School in Somers. The town, which sits 30 miles from White Plains and 55 miles from New York...

Eastern Parkway Trail

NY - 2 miles

The Eastern Parkway Trail is a 2-mile route along a tree-lined boulevard in Brooklyn's Crown Heights neighborhood. The path begins at Prospect Park, which houses some of Brooklyn's most popular...

Timp-Torne Trail

NY - 5.4 miles

Just an hour north of New York City, the Timp-Torne Trail offers a scenic hike through Bear Mountain and Harriman State Parks with panoramic vistas of the Hudson River. The rugged blue-blazed trail...

Old Croton Aqueduct Trail

NY - 22.8 miles

The Old Croton Aqueduct State Historic Park follows the route of the Old Croton Aqueduct, which carried water to New York City from 1842 to 1955. Most of the structure lies beneath the trail and has...

John Kieran Nature Trail

NY - 1 miles

The John Kieran Nature Trail is a short loop that borders Van Cortlandt Lake and its associated wetlands. It is a wonderful site for bird-watching. The trail also passes several sites of significance...

Jones Point Path

NY - 2 miles

The Jones Point Path occupies an abandoned motor vehicle route (old US Route 9W). The path provides bicyclists with a relatively safe bypass to a dangerous section of busy US Route 9W near Bear...

Naugatuck River Greenway

CT - 5.4 miles

The Naugatuck River Greenway will one day span 44 miles from Torrington to Derby in western Connecticut, but is currently open in a few short disconnected segments totaling just over 5 miles. The...

Hutchinson River Greenway

NY - 2.2 miles

The Hutchinson River Greenway offers a convenient alternative to the Hutchinson River Parkway, which it closely follows. Although adjacent to the busy thoroughfare, trees have been planted along the...

Recent Trail Reviews

Farmington Canal Heritage Trail

Best of Connecticut

July, 2017 by nimmorp01

Started in Hamdon and road to Southington. Round trip was 28.04 miles. Rented bicycles from Cheshire bike shop which was all of 50 feet from trail. Trail was nicely paved the entire way except for a very short detour.

New Milford River Trail

Access way a little rough

July, 2017 by linda.gaboardi

Once you get in the main trail, it's a nice, easy ride. But I picked up some kind of metal shard in my tire, and I suspect it was on the access trail that starts on Boardman.

Hook Mountain/Nyack Beach Bikeway

Trail construction again

July, 2017 by esobin

The last few years of construction was finally completed a few months ago and I was able to ride entire trail from Haverstraw to Nyack on my road bike (along with many other road bikers). It is just barely ok for experienced cyclists on the hilly northern section.
But I tried it again on July 10 and the Northern section is closed to everybody while they do some heavy construction work. There is also a short section of construction on the path that leads up to Rockland Lake but that is passible by walking.

Accordion

New Milford River Trail

Mostly Along River Road

July, 2017 by pbcibc

This is a nice place to stretch one's legs for about five miles. The southern end (just over Boardman Bridge from Route 7), with limited parking, runs through a town park for about 1.5 miles; the northern portion, ending at Gaylordsville, is just walking along the Housatonic on River Road, one of the few remaining dirt roads in the area. There is more parking at the park's main entrance off of River Road, about 1.5 miles north of Boardman Bridge.
If you like a flat trail in quiet woods and don't mind a few cars coming along, this is a pleasant way to spend a couple of hours. "There and back again" is about ten miles.

Cross Island Parkway Trail

Great trail

July, 2017 by cparache2

It is a wonderful bike ride. If you do it close to sunset, you can enjoy some rich colors overlooking the Throgsneck bridge.

Maybrook Trailway

Short but Sweet for a Mountain Biker

July, 2017 by jrjets08

Paved ends at Griffin rd. Bridge, but Black fence ends at Pumphouse rd...Hoping it goes further,Then i go east and it ends at the Train Tressel which i understand because it would cost to much to cross it i guess,but then the cutoff is at at Lisi's towing which baffles me but when i drive down Rt.6 in my Vehicle the Black Fence starts up again Hmmm!!!.

Derby Greenway

Meh.

July, 2017 by nyjenniferc

Full of goose crap. Loud and noisy. Thought it would be serene and picturesque by the river, but it was really industrial and boring, with no shade. The parking lot in Derby sucks. The bridge in Derby was full of firework debris, paper and junk. Very disappointed.

Air Line State Park Trail

Airline Trail South

July, 2017 by CW4

The Town of East Hampton and the State DEEP have added 1.3 miles of riding to the existing Airline Trail - South. It is hard to see the extension from the current ending on Route 196, but if you cross 196 and divert right and into the fire department parking lot you will find the new section. The new section goes to Alden's Crossing, a 1/2 mile from the intersection of Routes 16 and 66. The parking at the new ending is only marginal, 1-2 cars.

Harlem Valley Rail Trail

Hillsdale section now paved and open!

June, 2017 by billblum

I rode the newest 1.5 mile section from Anthony Street in Hillsdale to the Black Grocery Road trail head across the town line in Copake. It's a pleasant wooded section and a deer even crossed my path notwithstanding how close the trail runs to a residential section of Hillsdale. I then connected to the Orphan Farms Road to Undermountain Road section via a 3.3 mile detour, mostly on lightly traveled local roads with some gentle hills, to the Orphan Farms trailhead. Apparently this detour will be needed for some time since the plans for crossing both the Roe Jan Creek (near the Black Grocery trailhead) and NY Route 22, on the immediate opposite shore of the creek, have not yet been determined.

Heritage Trail (aka Orange Heritage Trail)

Paved from Monroe to Goshen

June, 2017 by sschwinn

I rode this trail from Monroe to its end at Hartley Road. It is paved from just east of Airplane Park (with a Korean War memorial including a fighter jet) in Monroe to Goshen. That 10 mile part is 5 star!

I gave it 4 stars overall because the trail is not well marked as it transits Goshen and the section from Goshen to the end point is a mix of gravel and dirt that I don't believe is suitable for a rode bike (it was OK on my cyclocross bike).

I started the section from Airplane park to Harriman but it is in worse condition than the west end would need a mountain or good hybrid to ride comfortably.

Sue Grossman Still River Greenway

Love the trail

June, 2017 by awinegar

My hubby and I have walked and have now began bike riding it. Walking it is great exercise. I have to say though the bike was a bit harder when riding against the wind ... lol... Everyone we came across was very polite. Walkers, bike riders, roller blades etc. I certainly give it a thumbs up...👍🏼

Shore Parkway Greenway Trail

Shore Parkway Greenway

June, 2017 by h.eiholzer

The stretch between Verrazano Bridge and Ceasar's Bay Shopping Center along Gravesend Bay is riddled with thousands of cracks and holes causing flat tires. This Bike trail has gotten worst ever since Hurricane Sandy hit the shores in October of 2012. Bike, Walk, Jog at your own risk. A disgrace for New York City.

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