Explore the best rated trails in New Milford, CT. Whether you're looking for an easy walking trail or a bike trail like the Walkway Over The Hudson and Windsor River Trail . With more than 69 trails covering 532 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 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...
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...
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 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...
The Quinnipiac River Gorge Trail is a 1.3-mile rail-trail in Meridan, Connecticut. The trail occupies the former railbed of the Meriden, Waterbury & Connecticut River Railroad, a 17-mile line which...
The Hartford Riverwalk is a charming network of paved pathways for cyclists and pedestrians that runs along the banks of the Connecticut River through the state capital. The trail provides an off-road...
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...
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,...
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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...
Bloomfield Greenway Multi-Use Trail is 1.8 miles between Bloomfield and Simsbury. The trail is envisioned to someday act as a connector between the City of Hartford and the Farmington Canal Heritage...
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...
This shared-use path was built as part of the improvement of NY State Route 347 in Suffolk County. SR 347 is a 15-mile arterial between Hauppauge and Port Jefferson, and the trail is envisioned to...
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 Windsor River Trail is a paved trail along the Connecticut River in Windsor Meadows State Park. The trail begins at the state park’s parking lot on E Barber St. The Captain John Bissell Trail,...
The Charter Oak Greenway offers more than 16 miles of paved pathway through Hartford and its eastern suburbs. At first glance, the trail looks as if it is simply a highway side path, but the journey...
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....
When completed, the Norwalk River Valley Trail will run from Danbury to Long Island Sound in southwestern Connecticut, for a total of about 27 miles. Currently, several disconnected sections totaling...
A dozen miles west of Connecticut’s capital of Hartford, the Farmington River Trail forms a 16.5-mile arc that connects to the larger Farmington Canal Heritage Trail on both ends. The rail-trail was...
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...
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 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...
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 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 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 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 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 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...
Bloomfield Greenway Multi-Use Trail is 1.8 miles between Bloomfield and Simsbury. The trail is envisioned to someday act as a connector between the City of Hartford and the Farmington Canal Heritage...
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 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...
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 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 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...
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,...
Over 2 miles from start to finish, this U-shaped trail meets both the commuting and the recreational needs of local residents in Middletown. The trail begins on Middle St, marked by a trailhead with a...
The Quinnipiac River Gorge Trail is a 1.3-mile rail-trail in Meridan, Connecticut. The trail occupies the former railbed of the Meriden, Waterbury & Connecticut River Railroad, a 17-mile line which...
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 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 Quarry Trail is currently a 600-foot long unimproved strip of land along what is known as Quarry Road in the Village of Hastings-on-Hudson, NY. The trail links Old Croton Aqueduct State Historic...
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 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 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...
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...
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...
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 Hanover Pond Trail is a mile-long rail-trail in Meriden, Connecticut offering scenic natural escape combined with historical exploration. The smooth asphalt trail is open to a diverse range of...
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 Hartford Riverwalk is a charming network of paved pathways for cyclists and pedestrians that runs along the banks of the Connecticut River through the state capital. The trail provides an off-road...
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 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 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...
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 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 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 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 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...
An enjoyable bike ride for the whole family ranging from my 4yr on her own bike to my parents in their mid-60s. We rode the paved trail between Wallkill and Walden during peak foliage in Oct and it was absolutely beautiful. Nice easy ride on smooth pavement, with scenery ranging from tree-lined countryside lane to more woodsy forested areas.
We did this in a Sunday afternoon and it was impossible to ride our bikes across. We walked most of the way and the views were great going over the bridge.
One of the best trails I have done. Nice and smooth. You must do Walkway over The Hudson.
We rode from New Paltz to a bit north of Rosendale trestle. Stopped for pizza at Rail Trail Cafe (delicious but really slow). View from the trestle is excellent, especially with the foliage almost peaking right now. The trail was in good condition but it hadn’t rained in a long time. Just north of the trestle there’s a cave you can explore on the right. Bring a good light.
Amazing ride in mid-October! Nice wide trail, mostly flat, plenty of benches to take breaks. Saw a beaver by its dam not far from the middle parking area
A nice 23 mile up and back from soundview. The most scenic part being from bronxville north to the dam. Definitely have a map handy though, as you will need to do street riding a few times. There are some hilly portions that will get you into gear changing which is nice. Bronxville has a great downtown with food options if you need to stop for a break. If this trail is ever connected it would be 5 stars for me. Solid ride and the dam at the conclusion is quite impressive.
My friend and I rode from Millwood on the North County Trail and just kept going. We ended up on the Putnam Trailway for a total of 46 miles. There are several decent hills on this segment of the trail. There are some street crossings but they are not very busy roads. You eventually come to the end of the trail, which is clearly marked. Near the end of the trail is a large reservoir. The trail is completely paved with just a few bumpy spots. We rode on 10/10 and the foliage has not changed much yet.
Level easy trail quiet and very pretty. Tricky entrance and exit onto busy road. Short easy trail. Wear boots muddy areas.
We started at Tait road entrance around 4:30 pm. Path was leafy but dry and good with great views.
Great trail. We took the fork to piermont and went over the TZ bridge. Awesome ride
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