Fairfield, CT Walking Trails and Maps

1213 Reviews

Looking for the best Walking trails around Fairfield?

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

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Activities
Length
Surfaces
Type
71 Results
Activities
Length
Surfaces
Type

Air Line State Park Trail

54.6 mi
State: CT
Ballast, Dirt, Gravel

Beach Channel Drive Greenway

1 mi
State: NY
Asphalt

Bethpage Bikeway

13.4 mi
State: NY
Asphalt

Branford Trolley Trail

0.6 mi
State: CT
Concrete, Crushed Stone, Gravel

Briarcliff-Peekskill Trailway

12 mi
State: NY
Asphalt, Dirt, Grass

Bronx River Greenway

23.3 mi
State: NY
Asphalt, Concrete

CTfastrak Multi-Use Trail

4.4 mi
State: CT
Asphalt, Concrete

Cross Island Parkway Trail

3.1 mi
State: NY
Asphalt

Derby Greenway

2 mi
State: CT
Asphalt, Dirt

East River Greenway

9.4 mi
State: NY
Asphalt

Eastern Parkway Trail

2 mi
State: NY
Asphalt, Concrete

Ellen Farrant Memorial Bikeway

5.5 mi
State: NY
Asphalt

Farmington Canal Heritage Trail

48.3 mi
State: CT
Asphalt

Farmington River Trail

16.5 mi
State: CT
Asphalt, Crushed Stone

Fort Washington Park Greenway

1 mi
State: NY
Asphalt

Hanover Pond Trail

1 mi
State: CT
Asphalt

Harlem Valley Rail Trail

17.2 mi
State: NY
Asphalt, Crushed Stone

Heritage Trail (NY)

15.1 mi
State: NY
Asphalt, Crushed Stone, Dirt

High Line

1.5 mi
State: NY
Concrete
Accordion

Hook Mountain/Nyack Beach Bikeway

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

Hudson River Greenway

12.9 mi
State: NY
Asphalt, Concrete

Hudson River Waterfront Walkway

1.5 mi
State: NJ
Concrete

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 Beach Boardwalk

4 mi
State: NY
Boardwalk

Jones Point Path

2 mi
State: NY
Ballast, Dirt

Joseph B. Clarke Rail Trail

4.1 mi
State: NY
Asphalt

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

3.1 mi
State: CT
Dirt

Larkin State Park Trail

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

Laurelton Greenway

0.6 mi
State: NY
Asphalt

Mattabassett Trolley Trail

2.9 mi
State: CT
Asphalt

Middlebury Greenway

4.5 mi
State: CT
Asphalt

Middletown Westlake Area Bikeway

2.2 mi
State: CT
Asphalt

Mohansic trailway

1 mi
State: NY
Boardwalk, Dirt, Gravel

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

20.7 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

26.5 mi
State: NY
Crushed Stone, Dirt, Grass, Gravel

Old Erie Path

3 mi
State: NY
Dirt, Gravel

Old Mine Railroad Trail

2.2 mi
State: NY
Dirt

Old Putnam Trail

1.25 mi
State: NY
Cinder, Dirt, Grass

Parks to Ports Greenway Trail

3.7 mi
State: NY
Asphalt

Pequonnock River Trail

13.6 mi
State: CT
Asphalt, Crushed Stone

Putnam Trailway

11.9 mi
State: NY
Asphalt

Quinnipiac Linear Trail

1.25 mi
State: CT
Asphalt, Gravel

Quinnipiac River Gorge Trail

1.3 mi
State: CT
Asphalt

Ramsey Bike Path

1 mi
State: NJ
Asphalt

Randall's Island Park Trails

8.75 mi
State: NY
Asphalt

Raymond G. Esposito Memorial Trail

1 mi
State: NY
Crushed Stone

Ridgefield Rail Trail

2.3 mi
State: CT
Gravel

Roosevelt Island Greenway

3.8 mi
State: NY
Asphalt

Saddle River County Park Bike Path

7.6 mi
State: NJ
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

13 mi
State: NY
Asphalt, Concrete

Shoreline Greenway Trail

4.1 mi
State: CT
Crushed Stone, Dirt

South County Trailway

14.4 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
The Air Line State Park Trail winds nearly 55 miles from the northeast corner of Connecticut, where the state borders Massachusetts, down to East Hampton in the heart of the state. The pathway is...
CT 54.6 mi Ballast, Dirt, 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 nicely paved Bethpage Bikeway runs alongside suburban roads for long segments of the route, but it’s much more than a suburban trail. Each on-road suburban stretch is broken up by one of three...
NY 13.4 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 0.6 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 travels from the mouth of the East River north to the Kensico Dam, providing views of the natural history of the area. Because the trail is under development, there are several gaps...
NY 23.3 mi Asphalt, Concrete
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
Running alongside both the Housatonic and Naugatuck Rivers, the Derby Greenway demonstrates a seamless integration of Connecticut’s natural river systems and parks with man-made interventions of the...
CT 2 mi Asphalt, Dirt
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
When Jones Beach State Park opened on Long Island’s South Shore in the late 1920s, a series of scenic parkways was built on infill dredged from nearby towns to connect New Yorkers to the new public...
NY 5.5 mi Asphalt
First a canal, then a railroad, and now a trail define the history of the Farmington Canal Heritage Trail. Completed segments span Connecticut south to north, from New Haven to the Massachusetts...
CT 48.3 mi Asphalt
A dozen miles west of Connecticut’s capital of Hartford, the Farmington River Trail forms a 16.5-mile arc that connects to the larger Farmington Canal Heritage Trail on both ends. The rail-trail was...
CT 16.5 mi Asphalt, Crushed Stone
The Fort Washington Park Greenway brings residents and visitors to Washington Heights right up to the edge of the Hudson. The mile-long trail begins near the pier at the end of Dyckman Street and...
NY 1 mi Asphalt
The Hanover Pond Trail is a mile-long rail-trail in Meriden, Connecticut offering scenic natural escape combined with historical exploration. The smooth asphalt trail is open to a diverse range of...
CT 1 mi Asphalt
Paralleling the Connecticut and Massachusetts borders, which lie only a few miles away, the Harlem Valley Rail Trail is a beautiful paved wooded pathway along the former New York & Harlem Railroad...
NY 17.2 mi Asphalt, Crushed Stone
Built on the former Erie Railroad main line, the 15-mile Heritage Trail runs through the small Orange County towns of Goshen, Chester, Monroe, and Harriman. The shaded trail runs through different...
NY 15.1 mi Asphalt, Crushed Stone, Dirt
The High Line trail runs 30 feet above the bustling Manhattan streets and sidewalks below, which for trail lovers makes it an attraction in the same league as the Statue of Liberty or the Empire State...
NY 1.5 mi Concrete
Accordion
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
The Hudson River Greenway (HRG) is one of the most popular places to ride, walk, and jog in New York City. It makes up part of the Manhattan Waterfront Greenway loop, the cross-state Empire State...
NY 12.9 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
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
The Jones Beach Boardwalk traverses Jones Beach State Park, running parallel (and south of) Ocean Parkway. The pleasant pathway offers views of the beach and the ocean. Although bicycles are...
NY 4 mi Boardwalk
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
You might expect a 4-mile rail-trail that passes through three downtowns to be excessively urban, but the quaint town centers on the Joseph B. Clarke Rail Trail are compact and surrounded by...
NY 4.1 mi Asphalt
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 3.1-mile Kress Family Trail in Roxbury occupies the former route of the Shepaug Valley Railroad (the Shepaug, Litchfield and Northern Railroad). The railroad was famously known as the “crookedest...
CT 3.1 mi Dirt
The Larkin State Park Trail meanders 10.8 miles through the woods and around the lakes and low hills of southwestern Connecticut. The rail-trail follows the route of the New York & New England...
CT 10.8 mi Cinder, Crushed Stone, Dirt, Gravel
The Laurelton Greenway is a short but well-maintained multiuse path connecting the neighborhoods of Jamaica and Rosedale in southern Queens, NY. The two-lane paved trail starts in Jamaica, and travels...
NY 0.6 mi Asphalt
Where a trolley once ran, now you can too on the south bank of the Mattabessett River. The electrified trolley shuttled passengers from Berlin to Middletown and beyond. The smooth blacktop and an easy...
CT 2.9 mi Asphalt
The Middlebury Greenway provides a paved, off-road option for a self-propelled journey across suburban Middlebury. The trail touches on several business districts and parks, ending at an amusement...
CT 4.5 mi Asphalt
Over 2 miles from start to finish, this U-shaped trail meets both the commuting and the recreational needs of local residents in Middletown. The trail begins on Middle St, marked by a trailhead with a...
CT 2.2 mi Asphalt
The Mohansic Trailway is a rail-trail providing an important link between the North County Trailway and the Franklin Delano Roosevelt State Park. The trailway occupies a short-lived spur of the New...
NY 1 mi Boardwalk, Dirt, Gravel
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 former “Old Put” commuter rail corridor that ran from the Bronx to northern bedroom communities in Westchester and Putnam Counties is popular once again, only this time it’s for people riding...
NY 20.7 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
Like Wantagh State Parkway, Ocean Parkway was built in the postwar 1930s to provide access to the crown jewel of the state park system, Jones Beach State Park. Unlike the former road, however, this...
NY 3.6 mi Asphalt
At first glance, there’s no evidence that an aqueduct ever existed along the Old Croton Aqueduct Trail. The trail is often a singletrack dirt pathway that winds through communities and trees and...
NY 26.5 mi Crushed Stone, Dirt, Grass, Gravel
The Old Erie Path reveals spectacular views of the Hudson River Valley as the rail-trail rolls along cliffs that border the river’s western shore. Although fairly short, it joins two other...
NY 3 mi Dirt, 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
This shared-use path was built as part of the improvement of NY State Route 347 in Suffolk County. SR 347 is a 15-mile arterial between Hauppauge and Port Jefferson, and the trail is envisioned to...
NY 3.7 mi Asphalt
The Pequonnock River Trail is not a name you will see on the ground along this developing trail in southwestern Connecticut. Formalized in 2001 by the state, the regional trail pieced together...
CT 13.6 mi Asphalt, Crushed Stone
The old New York Central rail line that ran from the Bronx to northern bedroom communities in Westchester and Putnam Counties carried commuters during the workweek, but on the weekends tourists...
NY 11.9 mi Asphalt
The Qunnipiac Linear Trail is an easy multipurpose path in Wallingford, Connecticut. The trail skirts Community Lake while traveling a heavily wooded corridor along the Quinnipiac River. It is one of...
CT 1.25 mi Asphalt, Gravel
The Quinnipiac River Gorge Trail is a 1.3-mile rail-trail in Meridan, Connecticut. The trail occupies the former railbed of the Meriden, Waterbury & Connecticut River Railroad, a 17-mile line which...
CT 1.3 mi Asphalt
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
Randall's Island Park Trails offer a series of interconnected paved loops on an island in the New York City borough of Manhattan. The park offers a quiet setting, especially enjoyed by runners, with...
NY 8.75 mi Asphalt
The Raymond G. Esposito Memorial Trail travels from one end of the village of South Nyack to the other in 1 mile but greatly expands its reach by connecting with the Old Erie Path and a new shared-use...
NY 1 mi Crushed Stone
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 County Park Bike Path is a beautiful suburban trail that winds alongside the Saddle River. Most of the trail runs through moderately dense suburban development, with residential and...
NJ 7.6 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 two diverse sections of the Shore Parkway Greenway Trail blend urban and scenic, offering views of sights ranging from the Statue of Liberty to wildlife refuges. Following the Belt/Shore Parkway,...
NY 13 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 4.1 mi Crushed Stone, Dirt
The South County Trailway rolls 14.4 miles through one of the most densely populated parts of New York, but its route through pocket woodlots, parks, and golf courses and along riverbanks makes it...
NY 14.4 mi Asphalt, Concrete
Coming in at just under 3 miles, the Sue Grossman Still River Greenway is anchored by the towns of Winchester to the north and Torrington to the south. It occupies the right-of-way of the Naugatuck...
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 William R. Steinhaus Dutchess Rail Trail—named for the county executive who championed it—is a local treasure in the Hudson Valley region of New York. The 13.1-mile trail runs through what seems...
NY 13.1 mi Asphalt

Now, More Than Ever, Trails Matter!

During COVID-19, trails are being counted on as places where people can find solace and respite and we need your support to keep trails open and provide these critical FREE resources! Please continue to practice physical distancing and check the status of your trail before heading out!

Trails by activity

Heritage Trail (NY)

NY - 15.1 miles

Built on the former Erie Railroad main line, the 15-mile Heritage Trail runs through the small Orange County towns of Goshen, Chester, Monroe, and Harriman. The shaded trail runs through different...

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...

Putnam Trailway

NY - 11.9 miles

The old New York Central rail line that ran from the Bronx to northern bedroom communities in Westchester and Putnam Counties carried commuters during the workweek, but on the weekends tourists...

East River Greenway

NY - 9.4 miles

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...

Accordion

Quinnipiac Linear Trail

CT - 1.25 miles

The Qunnipiac Linear Trail is an easy multipurpose path in Wallingford, Connecticut. The trail skirts Community Lake while traveling a heavily wooded corridor along the Quinnipiac River. It is one of...

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...

Kings Park Hike & Bike Trail

NY - 1.5 miles

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...

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...

Fort Washington Park Greenway

NY - 1 miles

The Fort Washington Park Greenway brings residents and visitors to Washington Heights right up to the edge of the Hudson. The mile-long trail begins near the pier at the end of Dyckman Street and...

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...

Quinnipiac River Gorge Trail

CT - 1.3 miles

The Quinnipiac River Gorge Trail is a 1.3-mile rail-trail in Meridan, Connecticut. The trail occupies the former railbed of the Meriden, Waterbury & Connecticut River Railroad, a 17-mile line which...

CTfastrak Multi-Use Trail

CT - 4.4 miles

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...

Joseph B. Clarke Rail Trail

NY - 4.1 miles

You might expect a 4-mile rail-trail that passes through three downtowns to be excessively urban, but the quaint town centers on the Joseph B. Clarke Rail Trail are compact and surrounded by...

Mattabassett Trolley Trail

CT - 2.9 miles

Where a trolley once ran, now you can too on the south bank of the Mattabessett River. The electrified trolley shuttled passengers from Berlin to Middletown and beyond. The smooth blacktop and an easy...

South County Trailway

NY - 14.4 miles

The South County Trailway rolls 14.4 miles through one of the most densely populated parts of New York, but its route through pocket woodlots, parks, and golf courses and along riverbanks makes it...

Hudson River Greenway

NY - 12.9 miles

The Hudson River Greenway (HRG) is one of the most popular places to ride, walk, and jog in New York City. It makes up part of the Manhattan Waterfront Greenway loop, the cross-state Empire State...

Randall's Island Park Trails

NY - 8.75 miles

Randall's Island Park Trails offer a series of interconnected paved loops on an island in the New York City borough of Manhattan. The park offers a quiet setting, especially enjoyed by runners, with...

Saddle River County Park Bike Path

NJ - 7.6 miles

The Saddle River County Park Bike Path is a beautiful suburban trail that winds alongside the Saddle River. Most of the trail runs through moderately dense suburban development, with residential and...

Bronx River Greenway

NY - 23.3 miles

The Bronx River travels from the mouth of the East River north to the Kensico Dam, providing views of the natural history of the area. Because the trail is under development, there are several gaps...

Farmington River Trail

CT - 16.5 miles

A dozen miles west of Connecticut’s capital of Hartford, the Farmington River Trail forms a 16.5-mile arc that connects to the larger Farmington Canal Heritage Trail on both ends. The rail-trail was...

CTfastrak Multi-Use Trail

CT - 4.4 miles

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...

Old Putnam Trail

NY - 1.25 miles

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...

Jack Harrington White Plains Greenway

NY - 1.2 miles

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...

Kress Family Trail

CT - 3.1 miles

The 3.1-mile Kress Family Trail in Roxbury occupies the former route of the Shepaug Valley Railroad (the Shepaug, Litchfield and Northern Railroad). The railroad was famously known as the “crookedest...

Accordion

Parks to Ports Greenway Trail

NY - 3.7 miles

This shared-use path was built as part of the improvement of NY State Route 347 in Suffolk County. SR 347 is a 15-mile arterial between Hauppauge and Port Jefferson, and the trail is envisioned to...

Klara Sauer Trail

NY - 1 miles

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...

Samuel G. Fisher Mount Ivy Environmental Park

NY - 2 miles

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...

Middletown Westlake Area Bikeway

CT - 2.2 miles

Over 2 miles from start to finish, this U-shaped trail meets both the commuting and the recreational needs of local residents in Middletown. The trail begins on Middle St, marked by a trailhead with a...

Old Croton Aqueduct Trail

NY - 26.5 miles

At first glance, there’s no evidence that an aqueduct ever existed along the Old Croton Aqueduct Trail. The trail is often a singletrack dirt pathway that winds through communities and trees and...

Pequonnock River Trail

CT - 13.6 miles

The Pequonnock River Trail is not a name you will see on the ground along this developing trail in southwestern Connecticut. Formalized in 2001 by the state, the regional trail pieced together...

Ocean Parkway Coastal Greenway

NY - 3.6 miles

Like Wantagh State Parkway, Ocean Parkway was built in the postwar 1930s to provide access to the crown jewel of the state park system, Jones Beach State Park. Unlike the former road, however, this...

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...

Bethpage Bikeway

NY - 13.4 miles

The nicely paved Bethpage Bikeway runs alongside suburban roads for long segments of the route, but it’s much more than a suburban trail. Each on-road suburban stretch is broken up by one of three...

North County Trailway

NY - 20.7 miles

The former “Old Put” commuter rail corridor that ran from the Bronx to northern bedroom communities in Westchester and Putnam Counties is popular once again, only this time it’s for people riding...

Laurelton Greenway

NY - 0.6 miles

The Laurelton Greenway is a short but well-maintained multiuse path connecting the neighborhoods of Jamaica and Rosedale in southern Queens, NY. The two-lane paved trail starts in Jamaica, and travels...

Sue Grossman Still River Greenway

CT - 2.9 miles

Coming in at just under 3 miles, the Sue Grossman Still River Greenway is anchored by the towns of Winchester to the north and Torrington to the south. It occupies the right-of-way of the Naugatuck...

Quinnipiac Linear Trail

CT - 1.25 miles

The Qunnipiac Linear Trail is an easy multipurpose path in Wallingford, Connecticut. The trail skirts Community Lake while traveling a heavily wooded corridor along the Quinnipiac River. It is one of...

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...

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...

Randall's Island Park Trails

NY - 8.75 miles

Randall's Island Park Trails offer a series of interconnected paved loops on an island in the New York City borough of Manhattan. The park offers a quiet setting, especially enjoyed by runners, with...

Air Line State Park Trail

CT - 54.6 miles

The Air Line State Park Trail winds nearly 55 miles from the northeast corner of Connecticut, where the state borders Massachusetts, down to East Hampton in the heart of the state. The pathway is...

High Line

NY - 1.5 miles

The High Line trail runs 30 feet above the bustling Manhattan streets and sidewalks below, which for trail lovers makes it an attraction in the same league as the Statue of Liberty or the Empire State...

Quinnipiac Linear Trail

CT - 1.25 miles

The Qunnipiac Linear Trail is an easy multipurpose path in Wallingford, Connecticut. The trail skirts Community Lake while traveling a heavily wooded corridor along the Quinnipiac River. It is one of...

Saddle River County Park Bike Path

NJ - 7.6 miles

The Saddle River County Park Bike Path is a beautiful suburban trail that winds alongside the Saddle River. Most of the trail runs through moderately dense suburban development, with residential and...

Accordion

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...

Shoreline Greenway Trail

CT - 4.1 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,...

Farmington River Trail

CT - 16.5 miles

A dozen miles west of Connecticut’s capital of Hartford, the Farmington River Trail forms a 16.5-mile arc that connects to the larger Farmington Canal Heritage Trail on both ends. The rail-trail was...

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...

Derby Greenway

CT - 2 miles

Running alongside both the Housatonic and Naugatuck Rivers, the Derby Greenway demonstrates a seamless integration of Connecticut’s natural river systems and parks with man-made interventions of the...

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....

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...

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...

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...

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...

North County Trailway

NY - 20.7 miles

The former “Old Put” commuter rail corridor that ran from the Bronx to northern bedroom communities in Westchester and Putnam Counties is popular once again, only this time it’s for people riding...

CTfastrak Multi-Use Trail

CT - 4.4 miles

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...

Bronx River Greenway

NY - 23.3 miles

The Bronx River travels from the mouth of the East River north to the Kensico Dam, providing views of the natural history of the area. Because the trail is under development, there are several gaps...

Hanover Pond Trail

CT - 1 miles

The Hanover Pond Trail is a mile-long rail-trail in Meriden, Connecticut offering scenic natural escape combined with historical exploration. The smooth asphalt trail is open to a diverse range of...

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...

Hudson River Greenway

NY - 12.9 miles

The Hudson River Greenway (HRG) is one of the most popular places to ride, walk, and jog in New York City. It makes up part of the Manhattan Waterfront Greenway loop, the cross-state Empire State...

Recent Trail Reviews

Cross Island Parkway Trail

Nice Ride

August, 2020 by jimft13

This is a short, well paved path. It has plenty of room but a bit noisy from the parkway.

New Milford River Trail

One Lot Only for Residents

August, 2020 by kbeaver147

My family and I took a lovely bike ride on this trail today. However, it’s important to share that (at least) one of the two parking lots (the southern-most one) is meant for New Milford residents only, and the cops will get your car towed if you’re not from New Milford. A true shame to exclude neighbors from enjoying the trail like that.

North County Trailway

smooth easy pavement

August, 2020 by thepoetsuede

An absolute joy for all bikes. Smooth well maintained trail which runs through a couple towns (not in the street) for easy access to grub.

Accordion

Heritage Trail (NY)

yep, it sure is flat!

August, 2020 by smajler

It’s flat, easy, well-paved and road-bike friendly. We ride folding road bikes with small wheels and found this trail very enjoyable. We biked from Monroe to Goshen. At the and of the trail in Goshen there is a small ice cream shop popular with the tourists and locals alike. A little past the end of the trail you can enter the town and have a picnic in the park. It’s a charming place.

Old Mine Railroad Trail

Mountain Bikes Only

August, 2020 by lughnerson

August 2020
Not my kind of trail. It is here, I did it, but did not enjoy it. Maybe I am lazy or spoiled by rail trails. VERY hilly, with trees I had to go over, under, and around. The trail does go past some very nice ponds, so it is worth a visit if you are a hiker or mountain biker.

Cross Island Parkway Trail

Short, but worth it

August, 2020 by lughnerson

Anything less than 5 miles is short for me, so 10 miles round trip. I combined this ride with another in the area near City Island. After driving past this path so many times I sought out the name and finally rode it, very happily. Park at Fort Totten and enjoy the great scenery. Lots of traffic noise near the road, but a small inconvenience for the views.

Bronx River Greenway

Beautiful. Ride the Dam

August, 2020 by lughnerson

A hot and humid Thursday in July 2020.
I started at the Kensico Dam in Valhalla and rode this path down to the first ending past White Plains. Twists, turns, over and under bridges and tunnels, it a very interesting and fun place to bike.

Make sure you ride up around the dam, both top and bottom for the glorious architecture, wonderful views and maybe a breeze. There is a quite steep and wide brick path to the right or east side when the greenway enters the park. If leaving the park it is on the left side. You will love it!

Air Line State Park Trail

Beautiful day on the Air Line

August, 2020 by SPanny

We rode this trail from Rt 85 parking lot to East Hampton and back on 8/1, about 20 total miles. We’ve always loved the Air Line…it has a varied feel as you proceed through the different town…the vast majority shaded, sections on a high ridge above a stream, two nice viaducts across what was once a trestle bridge, a section running through a nature preserve. There were a few sections a little rougher than others, and we observed a few places with protruding rocks that should really be removed (just keep your eye on the road), as well as some divots in the roadway, some caused by drainage. There are no major hills but you do have long gradual uphills like the one as you ride into East Hampton going west. But I think for most riders these will be small things in what, overall, is a great trail. Great to see many out on the trail on a sunny, warm day.

Farmington River Trail

The LoopTrail ( Farmington River Trail/ Farmington Heritage Trail) 28 miles

August, 2020 by czajk

We did the loop trail starting in Collinsville. Initially started towards Canton but turned around as wasn't sure where to head after the first mile and half and did loop towards Unionville. Take note of the insets on map as trail needs better signage when you get to the towns. Nice ride along river and through towns but a lot of stop and go across highways, some being busy but with pedestrian lights to stop traffic. Be careful getting to the State Park as busy road and uphill. In the park again poor signage and ended up on an incorrect trail and had to back track. ( Take stone dust trail by covered bridge not the one by swimming area) Once out of the park the trail runs on the road for approx 3 miles- make sure you take Lawton Road! Would have given it 4 stars but the stop and go and poor signage as well as distance on road was frustrating and took away some of the enjoyment. Note: During this pandemic saw very few people wearing a mask on trail and trail is not as wide as some others we've been on.

Bethpage Bikeway

Curvy, daring & worth it!

August, 2020 by thepoetsuede

Pros: Long trail with several entry points Mostly smooth Very nice tree coverage Nice trails for off ride riding Decent hills that challenge in a nice way Cons: Dangerous sharp blind turns Some slight ripples pavement at times Several stop and cross points

Maybrook Trailway

trail is most definitely closed

August, 2020 by linda.poughquag

The MTA has increased their warnings complete with fines for all to stay off the trail. No doubt in my mind whether or not it’s open. https://maybrooktrailway.org/

South County Trailway

great road

July, 2020 by chinabushell

Just finished a 30 mile ride on the trail. Started by VE Macy Park and ended right before Sleepy Hollow. Nice ride. The first 4 miles were bumpy but as you get further into Westchester the road gets smoother. Nice trail. Next time will ride 20 miles out.

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