Find the top rated trails in Port Chester, 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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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....
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...
The Randolph Trail system covers 16 miles of pathways through five parks, the Clyde Potts Reservoir watershed and 2,000 acres of pristine open space. The trails link schools and neighborhoods and also...
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...
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...
The 3.6-mile Middlesex Greenway connects the towns of Edison, Metuchen, and Woodbridge in northeastern New Jersey. The paved pathway, which follows the route of the former Lehigh Valley Railroad...
The West Essex Trail follows a short distance (just under 3 miles) of the former rail bed of the Caldwell Branch on the old Erie-Lackawanna Railroad. The trail runs between the Essex–Passiac county...
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...
The New Springville Greenway stretches just over 3 miles, primarily paralleling Richmond Avenue on New York's Staten Island. A highlight of the paved pathway is its proximity to Freshkills Park, a...
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A short rail trail with two covered bridges occupying a portion of the former Mount Hope Mineral Railroad right-of-way in Wharton, NJ. In the future this trail will be linked with the Rockaway...
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Much of New York's 15-mile 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 to Monroe. At Crane Park,...
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...
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...
The Walden-Wallkill Rail Trail is built on a former Conrail right-of-way. Conrail and its predecessors, Penn Central, New York Central, and The Wallkill Valley Railway, provided service to farmers...
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...
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...
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...
At 2.6 miles, the Staten Island Greenbelt Multi-Purpose Trail offers a nice jaunt for joggers, walkers, and cyclists alike. The crushed-stone path is 6-feet wide and runs from Rockland Avenue to...
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...
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,...
The Ellen Farrant Memorial Bikeway offers a paved bicycle and pedestrian route on the southwestern end of Long Island, paralleling Wantagh Parkway from Seaford to Jones Beach State Park. The trail is...
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...
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,...
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....
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...
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...
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...
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...
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...
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...
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...
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...
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...
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...
The Franklin D. Roosevelt Boardwalk follows Staten Island's eastern shore from Miller Field -- a recreational area for sports, picnicking and bird watching -- to Fort Wadsworth. Highlights of the...
The Perth Amboy Harbor Walk offers scenic views of the Raritan Bay and Raritan River as it hugs the shoreline of the City of Perth Amboy, founded in 1683 and home to one of the nation's oldest ports....
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...
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...
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...
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The Wood Duck Nature Trail, appropriately named for the secretive duck, was made possible through the hard work and dedication of refuge volunteers. This beautiful trail now extends about 1.5 miles on...
The Bronx River Greenway offers 23 miles of paved pathway in New York's Westchester and Bronx counties. The developing trail is open in disconnected segments largely paralleling the Bronx River...
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,...
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...
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...
Much of New York's 15-mile 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 to Monroe. At Crane Park,...
Brooklyn's Flatbush Avenue Greenway parallels its namesake roadway for just over a mile from Marine Parkway Bridge to a connection with the Shore Parkway Greenway Trail. The two trails are part of the...
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...
The Walden-Wallkill Rail Trail is built on a former Conrail right-of-way. Conrail and its predecessors, Penn Central, New York Central, and The Wallkill Valley Railway, provided service to farmers...
The New Springville Greenway stretches just over 3 miles, primarily paralleling Richmond Avenue on New York's Staten Island. A highlight of the paved pathway is its proximity to Freshkills Park, a...
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...
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...
The multi-use pathway spanning the length of New Jersey's Sandy Hook peninsula offers beautiful views of the ocean, as well as shady sections through maritime forest. A bird observatory and wildlife...
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...
The Ocean Parkway Trail closely follows its eponymous thoroughfare nearly 5 miles through several Brooklyn neighborhoods, ending only a block from the popular Coney Island boardwalk. Those traveling...
Hudson River Greenway stretches between Battery Park at the southern tip of Manhattan and the Little Red Lighthouse underneath the George Washington Bridge. The trail passes through Hudson River Park,...
This trail is in an area rich in geological history. Zinc and Iron Ores were transported along this branch from mines in the area that operated for over 200 years. The trail is scenic with a slight...
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...
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...
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...
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....
This trail is difficult to rate because it's so different in many places and we only rode about a quarter of it. It is not a true rail trail. Parking on Cedar Knolls Rd. in Whippany, we rode west into Lewis Morris County Park. What makes it confusing are the many, poorly-marked offshoot trails. Also, it's confusing because it's many different types of riding in one trail. It goes from road riding, to light trail riding, to mountain biking. There are spots where the trail ends with no direction as to where to go. Once you get into Lewis Morris County Park, it becomes mountain biking, roots and all. I would not attempt this part of the trail with a road bike. I had my hybrid with no suspension and ended up walking quite a bit. In some spots, you ride on rocks. The surface is slightly icy in some spots. The area around Speedwell Lake is nice and has some ruins of old buildings in the parking lot. If I ride this trail again, I would start further west. Morristown National Historic Park is located along the trail, which is a destination for next time. To optimize this ride, research the different sections and pick the one that's right for you.
The trail itself is pretty and mostly quiet. Great turns, gradual hills, not a lot of stops. For runners or wider tire cyclists, not bad. As a road cyclists, with a very stiff bike, it can be a bit jarring. Parts (about 3 miles up from Redmond Park) are basically corrugated roads. Extremely uncomfortable. You also have to be very alert to the changing conditions like sudden water and mud, and large unmarked dips and potholes. Really hard to maintain any speed over 17 or 18. Hoping this gets better maintained! Would be a treat to ride.
Just a mile or so due North is another EXCELLENT off-road biking destination: Wildwood State Park on Long Island Sound. 700 undeveloped acres of mountain biking and hiking trails open to the public.
https://parks.ny.gov/parks/68/details.aspx
Great ride, very easy, anyone can do it. It can be accomplished on a Road Bike. Surface was flat, smooth and clean.
I rode the northern section of the trail last week. I started at the Oakshades Park trail head, rode to the end at Popamora Point park, and then continued on a (mostly) marked on-street bike path to the Highlands Sea-Bright Bridge over to Sandy Hook. The trail was in very good shape with a few sections of root bumps. Fine for a road bike.
Once over the bridge I easily accessed the Gateway National Recreation Area multi-use path which allowed for fine cycling throughout the peninsula.
On the way back I took a detour to the Mt. Mitchill Scenic Overlook which, according to the signage, is the highest point on the eastern seaboard south of Maine.
Including some exploring of the historic sites included in the Recreation Area and the detour, about a 45 mile out and back.
This trail is a must, but be carful about the crowds.
This is a beautiful paved trail for biking, running, walking, strollers, and wheelchairs. It is well-kept and offers scenic views--from rolling fields, to bridges, to train cars, to even an old cemetery. My husband and I biked the entire length and back on a gorgeous fall day. It was a really nice ride, but be aware that it is often a false flat trail. One other major thing to be aware of is that you CANNOT access this trail from Mary Harriman Park in Harriman. Your best bet is to access if from Monroe. If heading east on the trail toward Harriman, the trail comes to a dead end fenced off bridge with no access and you're forced to turn around and go back the way you came. Hopefully someday they will fix this and extend it into Harriman for better access. That is my only complaint about this otherwise beautiful trail.
Newly paved trail is now open from the marina to Northern Blvd. This is a great ride especially during the week when it is not so crowded. As another reviewer stated one can extend their ride into nearby Fort Totten.
I love to walk the trail and have since 1971, the cross over on Whitney Ave in Trumbull is Terrifying, The cars cannot see any one passing the road way until they are in the roadway. The line of sight is completely obscured by vegetation and the small sign in the middle of the Street??? I have seen people run right across the road with out even slowing down prior to or while crossing Whitney Ave. I personally saw a woman hit the side of a car as she could not stop running in time to avoid the car. This section is an accident waiting to happen. Whitney Ave. crossing needs to be safer for both motorist and trail user.
At the end of the trail is a Kings supermarket with awesome sandwiches and more.
No meter parking along Kimball Ave before Palmer Rd.
To avoid getting lost trying to connect to the bike path after passing the Scarsdales Train Station: exit at the station go north on East Pkwy; Rt on Crane Rd; Lf on Fox Meadows Rd (after Fenimore Rd) it changes to Walworth Ave and Lf on Greenacres Ave. The 2nd entrance to the trail is about 1/5 mile on the right.
There are restrooms when you reach the Kensico Dam.
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