Find the top rated walking trails in Westport, 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.
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...
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...
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...
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 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 William R. Steinhaus Dutchess Rail Trail—named for the Dutchess County executive who championed it—is a treasure in New York's Hudson Valley region. The 13.1-mile trail runs through what seems...
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...
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...
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...
The Battery Bikeway is a only a half a mile long but it is an important link in the Manhattan Waterfront Greenway system, connecting the East River Greenway with the Hudson River Greenway to form a...
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...
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...
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...
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 Walkway Over the Hudson State Historic Park—the longest pedestrian bridge in the world at 1.28 miles—emerges from the trees and over the rooftops of the old riverfront town of Poughkeepsie,...
_199292_sc.jpg)
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...
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...
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 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 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...
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...
Note: As of December 2021, the trail is fully complete except for a bridge on its southern end in Brewster; stairways on either side of the bridge are available for the detour. Construction on the...
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...
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...
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,...
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...
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...
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...
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 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...
The Walkway Over the Hudson State Historic Park—the longest pedestrian bridge in the world at 1.28 miles—emerges from the trees and over the rooftops of the old riverfront town of Poughkeepsie,...
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...
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...
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...
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 EssexPassiac county...
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...
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...
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...
In the early 1830s the Morris Canal opened across northern New Jersey, from Phillipsburg on the Delaware River to Newark, and later to Jersey City on the Hudson River. It provided a thoroughfare for...
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 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...
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...
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...
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...
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...
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...
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 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...
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...
In the early 1830s the Morris Canal opened across northern New Jersey, from Phillipsburg on the Delaware River to Newark, and later to Jersey City on the Hudson River. It provided a thoroughfare for...
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...
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...
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...
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 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...
The Battery Bikeway is a only a half a mile long but it is an important link in the Manhattan Waterfront Greenway system, connecting the East River Greenway with the Hudson River Greenway to form a...
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...
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 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,...
As of 12/31/2021: The South Trail from the Tarrytown Lakes down to Ardsley is paved and a pleasant ride for bikers. At Ardsley it turns to crushed earth and unless you have a mountain bike probably not a good idea. I hope they extend the paving. The trail from the Tarrytown Lakes to Lake Carmel is smooth and beautiful. Highly recommend.
The entire trail is now reopened, with resurfacing from Springfield Blvd. to Winchester.
Rode this on a Summer day Parked by Quassy Amusement park and rode to Maggy My Fly's (a parking lot close to Maggy's, they do not allow parking). It was a mostly downhill ride on paved trail. Along the way there is plenty of green space and lots or roadway, there are a few short totally wooded sections but plan on looking at road for the bulk of your ride. Plenty of places to get food and drink along the way, and even a couple of public parks. This one was likely a one and done for me.
I walk this trail just about every morning. Plenty of parking off the Tuttle Place office park. Several options to increase the length or difficulty. Pretty well maintained but some of the fencing is starting to need attention.
From High School to Rt. 23 it’s bumpy and washed out in some areas. It was very nice after that and the water falls are an unexpected treasure. Overall we didn’t love it or hate it
This is a short yet beautiful bikeway that connects the Hudson River bikeway to the East River bikeway. You bike past large garden areas and have the option to take a quick detour off of the trail and into the park in order to take in views of the Statue of Liberty, Ellis Island, Staten Island and Governor’s Island.
We were looking for a ride that provided a good workout, beautiful foliage and a break from the city. The path was straight, flat and paved - so great for all level riders and all age people. The town of Goshen is great. The trail ends (or sort of starts there) depends which side of it you want to start on. There is a portion beyond Goshen in Middletown. To get to that piece - you need to go through the town of Goshen using W. Main Street. You must stop at Sweet Tymes for a treat. Continue to proceed down W Main Street for about 1/4 of mile and on the right you will see the start of the bike path again. You know you have gone too far if you get to the cemetery on the left side of W Main Street. I would also stop in Chester ( you will see the old converted train station) and grab a bite at the Rustic Wheelhouse. Promise it will be a perfect day!
Updating my July 2020 review, the road down to the Nyack Beach State Park has reopened.
And at the top of the newly reconstructed road to the right of the entrance fee kiosk is a newly constructed foot trail that will take you to the Long Path with access to the Hook Mountain summit with great river views.
Perfect surface. Lovely surrounding. Safe. Thoroughly enjoyable. Watch headwind, plan to have tail wind for return leg…
We started the trail in Middleport parking on Palmer Ave. Highly recommend this direction as it’s mainly uphill to Harriman. We clocked 19 miles exactly to Harriman. The uphill is not super intense but is uphill so the way back was super fun and easy! We stopped in Monroe on the way back to Middleport. 38 miles in total ALL PAVED and 99.5 % trail. Excellent. Little weird spot right before Goshen as the trail ends abruptly with no signs. Head into the main town of Goshen and turn right at the wine store and you’ll be back on track!
I have walked biked and jogged along greenway trails in Hauppauge along 347 from route 111 to Terry Road numerous times. Lately i run at night as do several others who i see along the trails. I have never seen the giant solar lights along the trail come on. The bus stop lights are on but the lamposts are never on and the paths are very dark I use a flashlight but others don't and it can be dangerous with debris along the pathway. I can't be the only one who as complained because it seems that since its inception they have never worked and i don't know why it took so long fpr me to complain. Concerned runner, Thank you
TrailLink is a free service provided by Rails-to-Trails Conservancy (a non-profit) and we need your support!
Map Search
_199292_st.jpg)
