Find the top rated trails in New Milford, 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.
_132561_st.jpg)
_157562_st.jpg)
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...
Shawangunk, Walden, and Wallkill Rail Trail is built on a railroad right-of-way that was abandoned by Conrail in the late 1970s. Conrail and its predecessors, Penn Central, New York Central, and The...
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...
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...
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 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 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...
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 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 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 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 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...
Built in 1888 to link New York and New England to the coal beds of Pennsylvania and the West, the steel cantilever truss Poughkeepsie-Highland Railroad Bridge was the longest bridge in the world for a...
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 Columbia Greenway Rail Trail offers just over 2 miles of paved, tree-lined pathway through Westfield in southwestern Massachusetts. The trail runs from Main Street, across the Great River Bridge...
Harlem Valley Rail Trail provides a scenic ride through rolling farm fields and dense woods on the bed of the New York and Harlem Railroad that ran from New York City to Chatham. The rail-trail is...
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...
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 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...
First a canal, then a railroad, and now a trail define the history of the Farmington Canal Heritage Trail. Completed segments span Connecticut south to north, from New Haven to the Massachusetts...
Note: Per the State of Connecticut's website, the trail is open from dawn to dusk April 1–November 14. Eagle nesting activities can delay the opening of the southern trail head in Windsor Locks. Due...
The Stratton Brook State Park Trail presents a great way to work up an appetite for a picnic at Stratton Brook State Park, the first state park in Connecticut to be entirely wheelchair accessible. 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...
Built in 1888 to link New York and New England to the coal beds of Pennsylvania and the West, the steel cantilever truss Poughkeepsie-Highland Railroad Bridge was the longest bridge in the world for a...
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 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...
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...
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...
Located in the mid-Hudson Valley is a remarkable trail that is picturesque and family friendly. This flat, paved Hudson Valley Trail stretches nearly 4 miles through hardwood forests, over Black Creek...
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...
The Cheney Rail Trail follows part of the corridor of the South Manchester Railroad, built by the Cheney brothers in 1869. The line was a 2.5-mile spur from the main Hartford, Providence, and Fishkill...
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...
Shawangunk, Walden, and Wallkill Rail Trail is built on a railroad right-of-way that was abandoned by Conrail in the late 1970s. Conrail and its predecessors, Penn Central, New York Central, and The...
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 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 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...
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 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...
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...
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 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 Cheney Rail Trail follows part of the corridor of the South Manchester Railroad, built by the Cheney brothers in 1869. The line was a 2.5-mile spur from the main Hartford, Providence, and Fishkill...
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 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...
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...
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...
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...
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,...
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 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...
Harlem Valley Rail Trail provides a scenic ride through rolling farm fields and dense woods on the bed of the New York and Harlem Railroad that ran from New York City to Chatham. The rail-trail is...
The Columbia Greenway Rail Trail offers just over 2 miles of paved, tree-lined pathway through Westfield in southwestern Massachusetts. The trail runs from Main Street, across the Great River 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 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...
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 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 Stratton Brook State Park Trail presents a great way to work up an appetite for a picnic at Stratton Brook State Park, the first state park in Connecticut to be entirely wheelchair accessible. The...
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...
Built in 1888 to link New York and New England to the coal beds of Pennsylvania and the West, the steel cantilever truss Poughkeepsie-Highland Railroad Bridge was the longest bridge in the world for a...
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...
Great ride but especially by IBM and where there is an active rusty river flowing there needs to be work done.
We were driving home to PA from CT and stopped to stretch our legs on this trail, so we didn't ride the full length. We started at Goshen and there was plenty of parking in the municipal lot that sits right at the trail head; this was a Monday afternoon, but there was still plenty of parking (thank you to the town for providing free parking!).
The trail is nicely paved and very well maintained. The first two miles were a bit noisy because the trail runs parallel to a busy highway, but after that it was quiet and relaxing. We went a bit beyond Chester and turned around. (Unlike some other reviewers, we didn't find Chester particularly charming.) The trail was flat, easy, well shaded, and relaxing, and we were grateful to the people who keep it in such good condition. Our only (VERY minor) complaint was that close to Goshen the trail sometimes had the feel of riding moguls, probably because tree roots are growing beneath the asphalt. Overall, we would recommend the trail.
After riding, we left our car in the municipal lot and walked two blocks to the Sunshine Cafe. Although the signage made us think it was just a juice bar, it had a nice menu--great paninis and a long list of specialty burgers. We recommend the restaurant highly.
I completed this trail this weekend. I started at the entrance of Beardsley Park and ended at Swamp Road in Botsford. The trail is beautiful and very quite. I highly recommend this trail. I would suggest stopping at Pepper Street as a portion of the trail between Pepper Street and Swamp Road is not really a trail. The "trail" is very narrow and overgrown ( I rode through this area with my arms pressed to my sides and still could not avoid the trees/leaves brushing against me). Also, the area has a very high concentration of mosquitos. All in all the trail is AWESOME and I will be riding it (up to Pepper Street) once a week.
The Trail Section approaching the MCC Road called "Great Path" has some extremely large cracks, 4-5 inches. If you're unaware as you approach they are very dangerous.....The Trail from Tolland Turnpike to Burnside Avenue aka Rt 44 is barely ridable because of all the many cracks and bumps. They have gotten worse in the last year....Lastly the trail between Burnside Avenue and Silver Lane, specifically , the first 360 degree curve under the highway has an extremely severe washout. Orange cones have been placed along the edge of the washout, but it is so extreme that someone coming around the blind corner, riding wide in the curve could be severely hurt should they loose control trying to avoid.
These sections of trail needs some serious work, but have not seen any work in years.
After reading some of the reviews I was prepared for a disastrous trail. Yes, its a little bumpy in spots but I felt it was mostly smooth. A couple of places are semi-rough but it wasnt that big of a deal.
Also, getting to it is a little tricky if youre just searching on google for directions. I found the best launch point to be at the northern most end of the South County Trail (just south-east of the Tarrytown Resovior). Drive your car to and get off at exit 23 of the Saw Mill Pkwy. There is a park and ride right there. Park your car and head south on your bike for the South County Trail and North for the North County trail.
I always attempt to start at one end of a trail and ride it to the end. According to the description the trail starts in Harriman which may have been the case at one point but as of July 2018 is not so. As others have said the trail ends abruptly at 12 miles and does not go to Harriman. I'd recommend you start at Crane Park in Monroe, it is easy to find and offers plenty of parking.
As far as the trail itself the scenery was average. The trail itself is all paved and mostly flat so it made for easy riding. The towns off of the trail are very quaint, I'd highly recommend walking around Goshen and visiting Chester for its local brewery. If you'd like to extend your ride try to find the unpaved extension in Goshen. It is single track and about two miles long so I'd take a mountain or hybrid bike.
From Wassaic to Copake, free parking in Wassaic train lot on weekends. Goes through a few small towns with bike shops including one in Copake. Lots of places to eat in the towns, some country roads tie the rail trails together, a few hills but nothing brutal, beautiful lake, plains, and frams views, and if you don't mind a small hike, check out Bash Bish falls in copake, worth the hike.
Nice ride! 44 miles round trip from Denniston road, Hybrid or mountain bike recommended. Great views from bridges. Surprising cold breezes from caves welcomed on hot days. Some muddy spots but overall very ridable.
I traveled from CT to come try this trail. Started cycling in Hopewell Junction and did the Dutchess trail, then the Walkway Over the Hudson, and the Hudson Valley trail out and back for 36 miles. Took a snack break then went back out to the Walkway and back for a total of 65 miles. Beautiful trail, clean and well kept and super clean bathrooms in Hopewell Junction. Definitely worth the trip. Hope to go back in the fall for autumn colors.
Rode the trail yesterday for the first time. Nice ride for an old guy like me. I started at the Oak Tree Road entrance and took it to the end and back. It’s a perfect trail for an older biker like me to get there daily exercise.
An excellent trail, takes you through mostly wooded areas, so you won't be riding in a blazing sun much. (Take mosquito spray). We started at Baldwin Place, next to New York Sports Club and took north (the trail actually runs both ways, north AND south, from NYSC - but the southern part is probably called differently; whatever the case, the trail map shows NYSC as the south entry point for Putnam Trailway).
If you start of heading north, your ride will be easy and pleasant - you'll spend most of time on a gentle downgrade, almost not touching your pedals. (Which means, of course, it's a harder work getting BACK - so, if you are doing a loop, maybe it's better to start off on the northern end of the trail and then have an easy ride back). The road is asphalt mainly, not in ideal conditions in many places, but nothing overly concerning - I saw people on racing bikes with thin rims. We had our folding and touring bikes, absolutely no issues.
If you are a family with kids, an ideal solution would be to start at the south entry point (NYSC), have an easy glide down, then split and have one of the parents ride back while the remaining party is waiting at one of the parking lots (there are benches in some places, and shops/cafes in others, so it's doable) and then come and pick them up by car.
Get Your 2018 RTC TrailNation Jersey!
Download the TrailLink mobile app and take TrailLink with you!
Donate and Get a FREE 2018 RTC Guidebook!
TrailLink is a free service provided by Rails-to-Trails Conservancy (a non-profit) and we need your support!
Map Search
