Find the top rated walking trails in Poughkeepsie, 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.
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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...
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 35-mile course through the former Albany-Hudson Electric Trolley corridor from Hudson to Rensselaer in New York State. The electric trolley ran for 30...
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...
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...
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 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 William R. Steinhaus Dutchess Rail Trail—named for the county executive who championed it—is a local treasure in the Hudson Valley region of New York. The 13.1-mile trail runs through what seems...
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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 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...
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....
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 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 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 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 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 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 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 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 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 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,...
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 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 Albany-Hudson Electric Trail (AHET) follows a 35-mile course through the former Albany-Hudson Electric Trolley corridor from Hudson to Rensselaer in New York State. The electric trolley ran for 30...
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 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 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 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,...
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...
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 Maybrook Trailway is a paved multiuse trail stretching across Putnam and Dutchess counties in New York state. The trail, which is owned and was built by Metro North Rail, occupies the former...
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 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...
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 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 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...
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 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 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 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 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 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 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 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 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 Walkway Over the Hudson State Historic Park—the longest pedestrian bridge in the world at just over 1.6 miles—emerges from the trees and over the rooftops of the old riverfront town of...
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...
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...
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 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...
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 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 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 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...
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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...
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 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 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...
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 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...
Parksville Rail Trail is one of our favorites! It’s gorgeous year round (though usually quite wet in parts, and icy in winter) but it’s one of our go to trails for a quick hike. Great for kids too!
Beautiful and well maintained…feels like it was built last night! Maybe could use a few benches but the real issue is the dangerous berms at the intersections mentioned by a previous reviewer. Truly horrible design! We saw a rider hit one hard. Fortunately he didn’t fall. They should be removed but in the meantime the curbs should be painted and potted plants placed on them to increase visibility. You will enjoy this trail just be safe.
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!
We biked the newly completed Under Mountain Road to Millerton. We have biked the other completed sections in the past and this newly completed section does not disappoint . Very scenic and easy ride with our hybrid bikes.
Well Maintained trail as we biked the central to western end. We would have biked the eastren side but it was closed for a maintenance reason. Turned out all the better as most of the scenic overlooks were on side we biked. Our hybrid bikes handled the packed stone trail very well. Would certainly return again
We started at the Hurley Marbletown Trailhead where the trail transitioned from pavement along SR 209 to all wooded. Trail is very scenic, that said trail has lots of ruts with no visual maintenance. We biked 1HR one way and turned around. Our bikes are hybrid and did not handle the poor grading very well. I would recommend wide tire bikes
Loved this ride. We rode from Columbia Plaza in EG to Nassau and back. Casual riding took 1 1/2hrs to get to Nassau (and much longer to get back- as it was our first ride this year-do we were tuckered out!). Lol. Miller RD (exit 10) Schodack has a convenient store which is about 1/2 way. So a great “pit-stop”. As was “smilees” ice-cream in Nassau and a Taco place “Diablos ?”sp across the way in Nassau.
We rode this trail for about 5 miles from the kilns, across the trestle, and south past farms and shaded trail. It was lovely. We quickly came upon a cave which was emitting cold air and stopped to take it in. No signage to inform you of this wonder. We brought a lunch and were disappointed to find no benches for the entire stretch. I just wanted to point these 2 things out as a way to improve the experience for others
I love this trail and the scenery. But there is a ditch with a crashed car at the bottom. The car is pretty old. Maybe late 70s or early 80s. It's between the parking space 17 park and ride lot in Monroe and the overpass. There's a green gate blocking the ditch. I would love to know more information about it if anyone knows.
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