Explore the best rated trails in Poughkeepsie, 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 56 trails covering 424 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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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 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 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...
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 City of Port Jervis is the latest community to save a portion of the former D&H Canal and turn it into a greenway for use by residents and visitors. A section of the canal, which is approximately...
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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 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 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,...
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 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 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 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...
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...
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...
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....
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 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 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....
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 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...
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...
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....
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....
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...
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 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 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...
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 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 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,...
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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...
This is a section of the New York, Ontario and Western (O&W) Railway line that ran across New York State from Port Jervis to Lake Ontario. The trail consists of two discrete sections: State Route 209...
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 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...
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 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 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 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...
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...
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 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...
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....
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...
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...
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...
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 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 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 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 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 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 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 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...
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 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....
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 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 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...
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.
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.
The Kennedy Catholic High School parking lot is private property and they have not given anyone walking the trail permission to access the trail via their parking lot . As with any school they are very protective of the student body and control who has access to the school and parking lot. DO NOT PARK IN THE SCHOOL PARKING LOT. Do not access the trail from the Kennedy Catholic High School.
What can I say, this is a great trail for a bike ride. Great scenery, flat for the most part and wasn't a lot of people. Must do trail
Great trail with beautiful views. In some section you're secluded (so be mindful) if alone. Trail is clean and flat best trail so far of 2022.
First half of the trail was overcome with traffic noise from the highway running parallel. Most of the path was uncomfortable gravel with very little scenery. 2.5 miles round trip but not inspiring.
Trail is nice for the size, well paved but hills. You can park on the back side of Maggie's and there are other places to park along the way.
I rode most of the Maybrook Trailway on a cold Easter Sunday in 2022. We started in Hopewell Junction and ended at a park right outside of Brewster. The trail is completely paved, very wide and in immaculate condition. There are mile markers but they are easy to miss and I wasn't quite sure what they were counting up or down towards as they did not start at 0. There are slight elevation changes that made riding back feel a little more difficult but there are no significant hills.
The scenery is nice but it is very monotonous with lakes being the only real variation to the trees and the disused railroad that encompasses the rest of the Maybrook Trailway. Since I did not make it all the way to Brewster proper I cannot speak to any sort of facilities there but the only real bathrooms or shelter/benches I found were at the very beginning in Hopewell Junction and where we ended near Brewster.
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