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 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...
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...
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...
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...
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 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 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...
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,...
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...
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...
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 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...
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...
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...
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...
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 Shore Parkway Greenway Trail is comprised of two disconnected segments along the New York Harbor that together offer 13 miles of paved pathway on Brooklyn's southern border. Between the two...
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 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 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 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...
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...
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 paved pathway running through West Hudson Park offers a scenic, tree-lined escape between Harrison and Kearny, NJ. The trail provides access to the park’s stocked lake, water park, athletic...
The Berkshire Valley Management Area Trail passes through hardwood forests and affords views of the valley below to the right. Equestrians must have a NJ Wildlife Permit, which is available from NJ...
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...
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 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...
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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...
Bergen County's Saddle River County Park Bike Path traverses a 577-acre linear park system that hugs the banks of the Saddle River and its tributaries. Five park areas are linked by the multi-use...
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 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...
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...
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 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...
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...
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...
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...
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 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...
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...
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...
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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,...
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,...
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...
In June 1986, the Morris County Park Commission dedicated this recreation trail that runs parallel to the New Jersey Transit Line railroad tracks. The trail was developed with the cooperation of the...
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 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...
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,...
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...
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...
This 2.1-mile long paved path runs directly adjacent to (about 30-40 feet off of) the Boulevard in Mountain Lakes, NJ, and follows the exact route of a former trolley line operated by the Morris...
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 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...
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...
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...
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...
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...
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 Shore Parkway Greenway Trail is comprised of two disconnected segments along the New York Harbor that together offer 13 miles of paved pathway on Brooklyn's southern border. Between the two...
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 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.
Paved path of just about 8.5 miles (all off the regular roadways) provides a great pathway for all skill levels. Beginners can take a leisurely ride with gradual inclines or more experienced riders can challenge themselves with speed and cadence. The path is completely free of roadway dangers as it is only open to walkers, bikers, skaters, etc. It has quite a bit of shady areas to stay out of direct sun due to its location near the woods. Some nice natural scenery. Start/end point located near Veteran Memorial and Isaac Dog Park for other points of interest.
This bike path needs to be Swept with a sanitation truck. Sweeper at least once a month I have gotten so many bike tire flats I usually ride from howard beach to the verrazano and back or I do the 20 mile loop to Rockaway and back home it needs a good cleaning and May be more lighting Thank YOU
Quick update that a stretch of trail less than one mile between Cornwall Av. and West Main St. in Cheshire is now officially opened, avoiding a detour onto Willow St. There is now a continuous, paved, off-road stretch of trail some 25 miles from Temple St. in downtown New Haven to Lazy Lane in Southington.
I have been on this trail for the last 10 years. I love this trail just for the scenery and the simple fact that its 10 minute drive away. But I recently discovered that there is a connecting rail trail. This is abandoned Erie branch line in Greycourt that passes through Washingtonville and rejoins the Erie Newburgh Shortcut at Vails Gate Junction in Vails Gate. This abandoned branch line runs directly in front of my house all the way to the orange Heritage trail. So instead of driving to this trail, I can actually can ride my bike and connect two trails.
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