Find the top rated trails in Westport, 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 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...
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Jones Beach Bikeway is a paved bicycle and pedestrian path on the southwestern end of Long Island that parallels Wantagh Parkway from Seaford to Jones Beach State Park. The trail is also known by two...
Owned by the Metro-North Railroad, the Maybrook Trailway starts at the Connecticut state line in Farringtons Park, and spans 5 miles into the town of Brewster. The trail follows what was once part of...
Roosevelt Island Greenway, 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 William R. Steinhaus Dutchess Rail Trail is a local treasure in the Hudson Valley region of New York, and for good reason: the 13-mile trail runs through what seems like a perpetually green...
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 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 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 Bronx River Greenway will one day stretch 23 miles along the river through New York's Westchester and Bronx counties. Currently, 18 miles of the trail are complete in disconnected segments largely...
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...
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...
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,...
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...
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...
Hudson River Greenway provides a continuous 11-mile route between Battery Park at the southern tip of Manhattan and the Little Red Lighthouse underneath the George Washington Bridge. The trail passes...
The North County Trailway is the longest of the four connected rail-trails breathing new life into the former New York Central Railroad's Putnam Division line. The "Old Put" provided passenger and...
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...
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...
These three contiguous trailsthe Raymond G. Esposito Memorial Trail, Old Erie Path and Joseph B. Clark Trailoccupy the former right-of-way of the Erie Railroad's Nyack and Piermont Branch. Each...
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...
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...
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...
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...
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 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...
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 Saddle River Area Bike Path in Bergen County stretches for nearly 6 miles along a 577-acre linear park system that hugs the banks of the Saddle River and its tributaries. There are actually five...
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...
The Old Croton Aqueduct State Historic Park follows the route of the Old Croton Aqueduct, which carried water to New York City from 1842 to 1955. Most of the structure lies beneath the trail and has...
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...
Jones Beach Bikeway is a paved bicycle and pedestrian path on the southwestern end of Long Island that parallels Wantagh Parkway from Seaford to Jones Beach State Park. The trail is also known by two...
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 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 Shore Parkway Greenway Trail is comprised of two disconnected segments along the New York Harbor that together offer more than 12 miles of paved pathway on Brooklyn's southern border. Between the...
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 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...
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 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...
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 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...
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 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...
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...
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,...
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...
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...
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...
These three contiguous trailsthe Raymond G. Esposito Memorial Trail, Old Erie Path and Joseph B. Clark Trailoccupy the former right-of-way of the Erie Railroad's Nyack and Piermont Branch. Each...
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...
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...
<p>This trail is the legacy of the first elevated roadway in the United States, constructed by William K. Vanderbilt in 1904. Vanderbilt created the parkway to get to his family’s estate in Long...
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 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 Shore Parkway Greenway Trail is comprised of two disconnected segments along the New York Harbor that together offer more than 12 miles of paved pathway on Brooklyn's southern border. Between the...
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....
The William R. Steinhaus Dutchess Rail Trail is a local treasure in the Hudson Valley region of New York, and for good reason: the 13-mile trail runs through what seems like a perpetually green...
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 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...
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 Portland section does not connect up to the East Hampton section and the rest of the Air Line Trail. I found out today when I thought I was going to ride from Portland to the Air Line Trail North. I only rode 2 miles and the trail abruptly ended.
The Air LIne Trail South is now open through part of Portland. Parking is off of Middle Haddam Rd. in Portland.
The never-ending road project actually had an end! The underpass is now open and the trail is rideable end-to-end!
We have ridden this trail before, and really enjoyed it, especially the part near the ponds below Oxford Airport. We expected it to be somewhat rough, and we are always willing to walk through particularly wet/mucky areas and to put up with rough stretches. However, the trail has really gotten much worse. After about 2-2.5 miles in, it became extremely sandy/silty, and we could only ride on the narrow edges. Then at about 4 miles in, there was a stream flowing through the whole trail, with nothing but mud and muck; no way to ride through, as it continued as far as we could see, so we had to turn around. End of ride for the day...
Absolutely beautiful scenery. Asphalt path was in great condition. People on the trail were friendly. Maps were available in Millerton as well as a clean porta potty. Many sections were shaded to provide some relief from the heat! Millerton is a small, quaint village with plenty of nice shops to check out.
The OCA trail offers a rich variety of surfaces and surroundings. I rode a commuter bike with 38mm slicks and did just fine, even through the muddy sections. I picked the trail up in Yonkers off the South County with a bit of street riding. This initial section runs through some rough spots in Yonkers and includes some on-street sections. After reaching the northern neighborhoods of Yonkers, it all starts to feel European with back-to-back posh villages, mansions, and views of the Hudson. There are even some interesting stone ruins, not to mention the Lyndhurst Mansion grounds.
The trail comes and goes a bit further north and you'll find yourself on the road more than you may like, but there are some deeply wooded sections and a fun climb to a bridge over Phelps Way. There is an aqueduct museum along the way and many clear signs of former aqueduct works.
I highly recommend this trail and shall return to it many times.
Nice Running Surface, trail is a little up and down for first 0.7 miles (starting from Gedney Way) so hard to get a running rhythm, but the wood chip surface is nice for running and it's shaded. Parked at the baseball fields close by - but looked like that parking lot filled up fast during softball season.
Just got my new gravel bike and this trail was a perfect bridal (horse) trail ride.Mud ,cinder,dirt and gravel are what you will encounter ,but the high berms,ponds and deep woods experience are worth the trip!
I rode my bicycle from the parking lot in Goshen NY to the end of the paved trail 12 miles long. There is a dead stop at 12 miles with a fence preventing you from advancing over an old bridge.
The trail is in great or perfect condition and some new repaving was noted along the way. Walk, run, bike, rollerblade or whatever your non motorized pleasure is. I noticed a few cameras along the trail and a police officer in a golf cart.
People were all nice and offered greetings as you pass. One thing to remember is a lot of people wear earphones/buds while using the trail and may not hear your warning when you are passing.
I find railroad trails feel like they are uphill both ways, the 24 mile ride was a bit much for my first ride this year.
Great trail, my congratulations to the caretakers of this wonderful trail.
Access to the southern portion through van cortlandant park goes thru an unpaved wooded area. Basically, mud, tree roots and stones--not ideal for road cycling. Once on the south county trail, things get better but not by much. For most of the trail, you will be greeted by uneven pavement, cracked asphalt and dips (smooth pot holes).
This trail will, in time, be incorporated into the Empire State Trail.
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