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.
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Note: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....
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 South County Trailway is a zippy paved trail heading north from Yonkers through the Hudson River Valley communities of Hastings-on-Hudson, Dobbs Ferry, Ardsley, Irvington, Greenburgh, and...
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 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 Derby Greenway runs between Division Street and Main Street, paralleling the Naugatuck and Housatonic rivers. The trail runs on top of a flood control dyke for the rivers; a portion of it goes...
The Southwick Rail Trail extends from the Massachusetts–Connecticut state line north to the Westfield town line and connects to the Columbia Greenway Rail Trail. Along the way, it travels through...
When complete, the Farmington Canal Heritage Trail will stretch from New Haven north to the Connecticut/Massachusetts state line. Currently, the trail spans nearly 50 miles with a gap in the middle...
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...
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 Farmington River Trail is built upon the former Central New England Railroad corridor and runs between the Farmington Canal Heritage Trail near Tunxis Meade Park and the Simsbury town line. A...
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 Kress Family Trail follows an old rail bed of the former Shepaug Railroad, which winds along the Shepaug River. The flat, out-and-back trail is popular with cross-country skiers and snowshoers in...
The delightful asphalt Middlebury Greenway winds 4.5 miles through the residential community of Middlebury, connecting businesses, parks and neighborhoods. The popular trail offers residents an...
The Charter Oak Greenway is a paved, multi-use trail connecting parks with residential and commercial areas. The trail runs for just over 13 miles between Manchester and downtown Hartford, though...
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 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...
The Wallkill Valley Rail Trail extends more than 20 miles between Kingston and Gardiner along the route of the old Wallkill Valley Railroad, which, in the late 1800s, carried produce from Ulster...
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Much of the 15-mile Heritage Trail, a.k.a. the Orange Heritage Trail, sails past wide fields of corn and wheat. The trail starts in Harriman at the Mary Harriman Park. From there, it heads northwest...
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 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....
Fahnestock State Park is a relatively undiscovered gems in the New York State Park System. Located a few miles east of Cold Spring Village on Rt. 301 (Main Street), the park jurisdiction was recently...
The Sue Grossman Still River Greenway runs for nearly 3 miles through a wooded corridor between Lanson Drive and Harris Drive in Torrington. The paved trail occupies the old right-of-way for the New...
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...
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Sandwiched between the Hudson River and the Catskill Mountains near the busy US Route 209 corridor, this trail has a little something for everyone. The Delaware & Hudson Canal Heritage Corridor (D & H...
The Charter Oak Greenway is a paved, multi-use trail connecting parks with residential and commercial areas. The trail runs for just over 13 miles between Manchester and downtown Hartford, though...
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 Wallkill Valley Rail Trail extends more than 20 miles between Kingston and Gardiner along the route of the old Wallkill Valley Railroad, which, in the late 1800s, carried produce from Ulster...
The Pequonnock River Trail—portions of which are also known as the Housatonic Railway Rails to Trails, Monroe Housatonic Railbed Trail and Pequonnock Valley Greenway—is a developing system stretching...
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...
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 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 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 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 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 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...
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 Southwick Rail Trail extends from the Massachusetts–Connecticut state line north to the Westfield town line and connects to the Columbia Greenway Rail Trail. Along the way, it travels through...
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...
Canopied with deciduous trees for most of its 10.8 miles, the Larkin State Park Trail (a.k.a. Larkin Bridle Path) is primarily a wilderness trail, with wooded vistas, wetland views and sparse...
The Charter Oak Greenway is a paved, multi-use trail connecting parks with residential and commercial areas. The trail runs for just over 13 miles between Manchester and downtown Hartford, though...
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...
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...
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...
The final passenger cars of the Putnam Division of the New York Central Railroad ran in 1958, but the rail line that so influenced development of this area still sparks nostalgia. The "Old Put"...
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 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 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 Kress Family Trail follows an old rail bed of the former Shepaug Railroad, which winds along the Shepaug River. The flat, out-and-back trail is popular with cross-country skiers and snowshoers in...
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—portions of which are also known as the Housatonic Railway Rails to Trails, Monroe Housatonic Railbed Trail and Pequonnock Valley Greenway—is a developing system stretching...
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...
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 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...
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 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...
When complete, the Farmington Canal Heritage Trail will stretch from New Haven north to the Connecticut/Massachusetts state line. Currently, the trail spans nearly 50 miles with a gap in the middle...
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...
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...
This trail is beautiful in the fall. Well maintained and mostly paved. Its a smooth ride but gets a bit rocky crossing between bolton and vernon. Other than that this trail is amazing. Can be a bit crowded on weekends though
After heavy rain on April 16th, the trail along the Willimantic River is temporarily flooded and impassable,
Went for the first time yesterday. it was beautiful. Nice and wide, not over-crowded. some hills for a bit of a challenge and best part is that I was able to bring my fur baby in a safe walking environment . .
very safe plenty of hills good visibility nice and wide
I started at Watch Hill Rd near the shooting range, over the Croton Gorge, and up the road. The trail continues across the street but it’s hard to find and doesn’t look like a trail. It heads through Tea Town and is very nice for a few miles. Once you get near Rte 134 it’s a mess. Apparently it continues for another mile or two but I turned around at 134. Very nice in spots, especially when all the trees are in, say May-June.
While i believe there is a short break around the town of Accord where the "trail" is on the curb of the road for a quarter mile, this trail I believe picks up again and continues as far as Ellenville. At least thats what maps on the trail suggest, thouh i have yet to hike that far down myself.
Its also worth noting that the county has plans to eventually join this trail with the Walkill Valley trail and the trail by Kingston Point beach (not on this site). Ive also heard there are plans for another trail along the rail line from Kingston to Poughkeepsie. How much of this is just talk and how much is actually being put into action i have no idea tbh.
The new portion heading under the Merritt Parkway entrances (via tunnels) are installed and old train bridge over Rt 15 is now open and it's complete.
It is a continuous trail from Bridgeport (Beardsley Park) to Newtown.
Great work in completing this section.
Now we need to get Newtown on board to extend it.
The previous reviewer indicated there was standing water on the trail in Andover. This is due to frost-thaw cycle that starts in November. The stone dust trails become very mucky once this starts and makes cycling a bit harder and messier. Paving would solve the problem.
This trail is great; what a gem. I can see why the locals refer to it as a favorite. The two reasons we didn't rate it a 5 is the standing water on a couple sections near Andover, CT (there's been no rain in days) and secondly, for a 3-wheeled recumbent trike -- the un-passable automobile barriers at the road crossings (had to carry our trike over the stones adjacent to the barrier). The trail has a few areas with small grades but for the most-part is really flat. The trail surface is hard packed, we saw numerous skinny wheeled street bikes experiencing no difficulties once so ever. The trail is heavily used but everyone we encountered was respectful of other users right-of-way. My wife rode the trail on a recumbent trike and I on a Mt bike.
I love it! Took some photography photos on the bridge and might have even climbed a bit
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