Explore the best rated trails in Kingston, NY. Whether you're looking for an easy walking trail or a bike trail like the Tannersville Bike Path (Huckleberry Multi-Use Trail) and Walkway Over The Hudson. With more than 42 trails covering 369 miles you’re bound to find a perfect trail for you. Click on any trail below to find trail descriptions, trail maps, photos, and reviews.
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The Railroad Ramble occupies a corridor abandoned by the Central New England Railroad, which provided service from 1871 through 1967. In Lakeville, the trail can be found just off of Route 41 behind...
Following the route of the former Delaware & Hudson (D&H) Railway, the Albany County Helderberg-Hudson Rail Trail serves as a scenic oasis and community connector for residents living southwest of...
The Bashakill Wildlife Management Area is located on the Orange County-Sullivan County border just south of Wurtsboro, New York. It consists of over 3,000 acres of wetlands and uplands which were...
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...
Offering a picturesque and family-friendly adventure, the Hudson Valley Rail Trail stretches 7.1 miles through hardwood forests, over Black Creek, and under two spectacular stone-arch bridges....
Open in several disconnected segments, the Billings Trail is a dirt path that traverses a lovely scenic and wooded landscape outside Norfolk in northern Connecticut. Built on the abandoned railbed of...
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 Albany-Hudson Electric Trail (AHET) follows a 36-mile course through the former Albany-Hudson Electric Trolley corridor from Hudson to Rensselaer in New York State. The electric trolley ran for 30...
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...
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...
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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 O&W Rail Trail provides a glimpse into the area’s history from the perspectives of both a historical canal and a railroad. The Delaware & Hudson (D&H) Canal carried coal from Honesdale,...
The Liberty Rail Trail extends about 2.5 miles through the village of Liberty, NY, between Chestnut Street/SR 52 (near West Street) and the old rail trestle in Ferndale. The trail occupies a portion...
Connecting the Walkill River and Shawangunk Ridge, the aptly named River-to-Ridge Trail, which opened in September 2018, runs from New Paltz to the Mohonk Preserve. Begin at the Carmine Liberta Bridge...
This rustic unpaved trail, just over three miles in length, runs along a route formerly used by the New York, Ontario, & Western Railway's Main Line through Parksville in Sullivan County, NY. The...
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 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 5.5-mile trail is the rail-trail section of two much longer trails, the Long Path and the Shawangunk Ridge Trail, that converge and share the same path for part of their respective routes. Built...
The D & H Canal towpath is nestled within the 300-acre D & H Canal Park in the New York hamlet of Cuddebackville. The crushed-stone trail, stretching just over a half mile, is one section of a larger...
The Kennedy Trail begins at Brick Hill Road and ends at the northwest corner of the 68-acre campus of John F. Kennedy Catholic High School in Somers. The cinder trail, built on a former rail bed,...
While the Wallkill Valley Railroad no longer carries fruits and vegetables from Ulster County to New York City, trail users can still discover small, family-owned farms and farmers markets serving up...
The Albany-Hudson Electric Trail (AHET) follows a 36-mile course through the former Albany-Hudson Electric Trolley corridor from Hudson to Rensselaer in New York State. The electric trolley ran for 30...
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 Kingston Point Rail Trail will be a paved pathway stretching from Kingston’s midtown to the Rondout Creek waterfront, connecting important points in the community such as Kingston High School,...
The Andes Rail Trail begins in the quaint town of Andes in the beautiful Catskill Mountains region of southeastern New York and follows a branch of the former Delaware and Northern Railroad. At the...
The Kaaterskill Rail Trail offers a beautiful wooded walk through Haines Falls in eastern New York, nestled in the northern Catskills. It begins at the historical Ulster & Delaware Train Station,...
The Kennedy Trail begins at Brick Hill Road and ends at the northwest corner of the 68-acre campus of John F. Kennedy Catholic High School in Somers. The cinder trail, built on a former rail bed,...
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 Bashakill Wildlife Management Area is located on the Orange County-Sullivan County border just south of Wurtsboro, New York. It consists of over 3,000 acres of wetlands and uplands which were...
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 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...
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For family riding and walking, the Tannersville Bike Path offers a 2.7 mile stretch of graded dirt path starting on Clum Hill Road directly across from Cortina Valley. The opposite end is on Bloomer...
The O&W Rail Trail provides a glimpse into the area’s history from the perspectives of both a historical canal and a railroad. The Delaware & Hudson (D&H) Canal carried coal from Honesdale,...
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...
The Ashokan Rail Trail is an 11.5-mile multi-use trail that traces the northern edge of the Ashokan Reservoir, which provides a large proportion of New York City's drinking water. The trail sits on...
The Catskill Scenic Trail lives up to its name as it winds through a broad farming valley and small towns in New York's Catskill Mountains. The West Branch of the Delaware River is often in sight,...
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...
Following the route of the former Delaware & Hudson (D&H) Railway, the Albany County Helderberg-Hudson Rail Trail serves as a scenic oasis and community connector for residents living southwest of...
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...
This 5.5-mile trail is the rail-trail section of two much longer trails, the Long Path and the Shawangunk Ridge Trail, that converge and share the same path for part of their respective routes. Built...
The Kennedy Trail begins at Brick Hill Road and ends at the northwest corner of the 68-acre campus of John F. Kennedy Catholic High School in Somers. The cinder trail, built on a former rail bed,...
The Kaaterskill Rail Trail offers a beautiful wooded walk through Haines Falls in eastern New York, nestled in the northern Catskills. It begins at the historical Ulster & Delaware Train Station,...
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...
With vistas of the Catskill Mountains and a vast blue lake, the Ashokan Reservoir Promenade is a stunner. The paved pathway begins in Olivebridge, a hamlet in southeastern New York, and spans just shy...
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...
This 5.5-mile trail is the rail-trail section of two much longer trails, the Long Path and the Shawangunk Ridge Trail, that converge and share the same path for part of their respective routes. Built...
The Railroad Ramble occupies a corridor abandoned by the Central New England Railroad, which provided service from 1871 through 1967. In Lakeville, the trail can be found just off of Route 41 behind...
The Liberty Rail Trail extends about 2.5 miles through the village of Liberty, NY, between Chestnut Street/SR 52 (near West Street) and the old rail trestle in Ferndale. The trail occupies a portion...
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...
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...
The Catskill Scenic Trail lives up to its name as it winds through a broad farming valley and small towns in New York's Catskill Mountains. The West Branch of the Delaware River is often in sight,...
Open in several disconnected segments, the Billings Trail is a dirt path that traverses a lovely scenic and wooded landscape outside Norfolk in northern Connecticut. Built on the abandoned railbed of...
The Andes Rail Trail begins in the quaint town of Andes in the beautiful Catskill Mountains region of southeastern New York and follows a branch of the former Delaware and Northern Railroad. At the...
The Delaware & Hudson Canal Linear Park is 45 acres with a trail situated along the historic D&H Canal. Remains of the original locks, dry dock and waste weirs are visible from the towpath trail....
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...
Following the route of the former Delaware & Hudson (D&H) Railway, the Albany County Helderberg-Hudson Rail Trail serves as a scenic oasis and community connector for residents living southwest of...
The Kingston Point Rail Trail will be a paved pathway stretching from Kingston’s midtown to the Rondout Creek waterfront, connecting important points in the community such as Kingston High School,...
The Albany-Hudson Electric Trail (AHET) follows a 36-mile course through the former Albany-Hudson Electric Trolley corridor from Hudson to Rensselaer in New York State. The electric trolley ran for 30...
This rustic unpaved trail, just over three miles in length, runs along a route formerly used by the New York, Ontario, & Western Railway's Main Line through Parksville in Sullivan County, NY. The...
The Ashokan Rail Trail is an 11.5-mile multi-use trail that traces the northern edge of the Ashokan Reservoir, which provides a large proportion of New York City's drinking water. The trail sits on...
I drove the 70 miles from my home in Manhattan, not an easy drive both northbound and return given traffic. A friend suggested a parking place just South of Wassaic Station that is free all the time. Location is 14 Main Street, Wassaic, NY. I rode the 23 miles North to the point that the trail turns East along a public road. I turned around not because of riding on a public road, after all I ride in Manhattan, but because I would already have 50 miles before I got home. The trail is paved and mostly smooth. The multiple bridges are concrete slabs and a few are wooden. All have distinctive railings made of wood joined by steel cables. They compliment the natural trail very well. It is the CLEANEST trail that I’ve ever cycled, I saw only ONE discarded plastic bottle and it was down a ravine. Negatives: Pack an extra water bottle, I had two and rationed it carefully. I found NO place to buy a drink or snack. Take extra trail mix! There is only one intersection with heavy traffic. On the ones with very light traffic I found that the vehicles would stop and let you pass. Caution, just because the westbound car stopped that’s no guarantee that the eastbound vehicle will be as considerate. Few porta-potties; the ladies may not be pleased.
We rode the Electric Line trail from Stuyvesant Falls to North Chatham on 6/20/22. First thing you need to know: use the actual Empire State Trail website to get maps and directions; as of this writing, Google’s routing is incorrect and missing several sections. The trail is partly stone dust and partly paved, and includes a few on-road sections which were easily navigated. In fact, the signage on this trail was the best I’ve ever seen! Almost every trail crossing has a user-activated light, even though in most cases the traffic is minimal. I loved the variety – you go past farms, along creeks, past several reservoirs, and skirt your way past some nice small towns like Kinderhook and Valatie. The engineers did a great job with the routing of the trail here. There’s a short section where the trail moves on-road (Route 9) which is a bit busy, but we just avoided that by riding a short distance on the sidewalk. Lots of signage describing the history of the area. The trail was in great condition and fun to ride. After having ridden many other trails in the Hudson valley (the Wallkill, the Dutchess, the Maybrook, the Harlem Valley), so nice to have another great trail to add to the list!
The Maybrook has quickly become one of our favorite rail trails. Basically brand new, uncrowded, lots of interesting sights along the way including multiple water views and lots of greenery.
Today we rode from the Brewster trailhead at Lake Tonetta both ways: Out and back to the CT line, and then out and back in the other direction up past the Ice Pond, for a total of about 20 miles. The first segment to the CT line was new to us; there is an on-road detour due to a bridge out at Peaceable Hill Road. You walk down a flight of steps, ride down Peaceable Hill Road to Rt. 6, turn left on Rt. 6, go down the hill, turn left again on Rt 6 and then ride up the hill past the Honda dealership where another set of stairs on the left will bring you back to the trail. These stairs are fairly steep but it can be done. The road has a shoulder but is a bit busy; experienced road riders will find this easy to navigate, others can simple walk along the sidewalk. Your reward is that the other end of the trail as you ride east is a very nice section past East Branch Reservoir, including a long section right along the water. One way mileage is about 5 miles, as the trail ends at the Connecticut line. The second section we rode, going North from the Brewster trailhead at Lake Tonetta, offers views of the “ice pond” and the “great swamp,” with hills in the distance. Today’s one way mileage for that section was also about 5 miles; a great ride, and you can ride much farther (we often go as far as Whalley Lake, just not today) as the trail goes all the way to Hopewell Junction where you can pick up the Dutchess Rail Trail. Check the Empire State Trail website for more info.
Rode the full trail on Memorial Day and really enjoyed it. It is well maintained; smooth pavement all the way. Mostly good shade and scenic, with lots of woods. A few spots along busy roads, but the trail is well protected throughout; always a sturdy railing between you and the cars. Goes through a few towns for snacks or lunch. Others warned about it being uphill heading north but I found it mostly flat. Some uphill as you approach the Putnam border, but mostly a gentle grade. Never came out of the seat. Overall a great trail.
Rode the full trail on Memorial Day and really enjoyed it. It is well maintained; smooth pavement all the way. Mostly good shade and scenic, with lots of woods. A few spots along busy roads, but the trail is well protected throughout; always a sturdy railing between you and the cars. Goes through a few towns for snacks or lunch. Others warned about it being uphill heading north but I found it mostly flat. Some uphill as you approach the Putnam border, but mostly a gentle grade. Never came out of the seat. Overall a great trail.
I started today by the Wurtsboro Fire house and managed a nice 3.5 mile run. I consider this a great trail for anyone who wants to loop around instead of doing and out and back run/walk. Some of the rail trail needs some upkeep but it’s still doable. Great hidden gem in the community.
My friend and I started at Hopewell Junction and glad we did. It was a nice leisurely ride up to Walkway on the Hudson in Poughkeepsie. The trail is very well maintained, and an easy ride. We locked the bikes up by the walkway, headed into town for an incredible lunch. I only wish it were more scenic but very happy we chose this way to ride.
I did the loop from the Clinton Street parking area to North Chatham. The trail is nicely paved with new guardrails and clearly market. Several street crossings have the flashing light activation button to cross roads safely. There are a few convenience stores on the way in case supplies are needed, and there is an ice cream and lunch place on the trail in Nassau. There are a few sections you need to ride on the road, but they are back roads through neighborhoods not a lot of traffic
Very consistent trail with a variety of lake, stream and Mountain View’s. A short jaunt from a mid-way entrance takes you to Fruition, a nice chocolate/ ice cream spot. Saw a snapping turtle, deer and a beaver dam & lodge. Nice information signs along the way. Given a nice Saturday, trail was thinly traveled. Did ride with E-Bikes.
I have been riding parts of this trail for about 24 years. It now goes from Harriman to downtown Middletown. To find the new section from Goshen to Middletown you have to go up West Main street in Goshen just past Clowes Ave on left then make a right where there are no trespassing signs and you will see the trail on your left. The big issue with this entire trail is about 60% of the people using it do not know or follow the rules. If one simple rule was followed, 100% of the issues would be eliminated. Walk, ride jog and skate on the right side of the trail and allow people to pass you on the left. Simple as that. Do not ignore verbal warnings or bicycle bells. When you hear a warning move to the RIGHT! I constantly encounter people using the middle or left side of the trail and ignoring warnings to move right. Many people have no concept of the fact that every time they use the trail, faster moving traffic WILL come up behind them. I have people move left after a warning, I have people refuse to move at all and I have people that stop and glare at you for ringing a bell or announcing a verbal warning. Bells and warnings are for safety people!!! I encounter people who ride bikes in groups that block the entire trail and fail to move right after a warning. It amazes me how confused people are. One simple rule people. One simple rule! Move right and stay right!
The Kennedy Catholic School is private property. Do not enter or depart the trail from the southern endpoint at Kennedy Catholic.
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