Find the top rated trails in Cheshire, 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.
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 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 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...
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...
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 Southwick Rail Trail is now complete from the Massachusetts–Connecticut state line, where it continues south as the Farmington Canal Heritage Trail. On the north end, the trail extends to the...
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 Hop River State Park Trail is one of Connecticut's longest rail-trails. Narrow cuts and a lush tree canopy make for enjoyable visits year-round. Near its western end is the Charter Oak...
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 Chicopee Center Canal Walk offers a short pleasant route in Chicopee, a small city on the outskirts of Springfield in southern Massachusetts. The pathway closely follows the slow-moving canal and...
The Connecticut River Walk and Bikeway, which will one day run 21 miles along the river, currently has two open segments. The longest stretches 3.7 miles from the Chicopee town line to the South End...
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...
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 delightful asphalt Middlebury Greenway winds 4.4 miles through the residential community of Middlebury, connecting businesses, parks and neighborhoods. The popular trail offers residents an...
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...
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Thanks to skilled engineers with the former Hartford, Providence, & Fishkill Railroad, the pretty Vernon Rails-to-Trails overlooks ravines and streams and passes between rock walls verdant with ferns...
The Redstone Rail Trail is built on the former New York, New Haven & Hartford Armory Branch, which in turn is a former branch line of the New York & New England RR. Its name comes from the numerous...
The EPCAL Alternative Transportation Path loops around the 2,900-acre Enterprise Park at Calverton (hence its name: EPCAL) on New York’s Long Island and links to the Town of Riverhead’s 65-acre...
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The Trolley Trail runs through Plainfield and is a key link the East Coast Greenway. Plans are to use this trail as a link between the Moosup Valley State Park Trail and the Airline State Park...
The Redstone Rail Trail is built on the former New York, New Haven & Hartford Armory Branch, which in turn is a former branch line of the New York & New England RR. Its name comes from the numerous...
The Kress Family Trail follows an old rail bed of the former Shepaug Railroad, which winds along the Shepaug River. The flat, 2.5-mile trail is popular with cross-country skiers and snowshoers in...
Running north from the Yale University campus in New Haven through the heart of Connecticut, the multi-use Farmington Canal Heritage Trail, when completed will stretch uninterrupted more than 80 miles...
The Trolley Trail runs through Plainfield and is a key link the East Coast Greenway. Plans are to use this trail as a link between the Moosup Valley State Park Trail and the Airline State Park...
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...
Note: Per the State of Connecticut's website, the trail is open from dawn to dusk March 1–November 30. The 4.5-mile Windsor Locks Canal Trail follows the Connecticut River and the Windsor Locks...
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 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 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 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...
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 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...
Air Line State Park Trail winds for just over 55 miles from the northeast corner of Connecticut, where the state borders Massachusetts, down to East Hampton in the heart of the state. Over the state...
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...
Columbia Greenway Rail Trail offers 2 miles of paved, tree-lined pathway through Westfield in southwestern Massachusetts, from Main st, across the Great River Bridge over the Little River to the...
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 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 EPCAL Alternative Transportation Path loops around the 2,900-acre Enterprise Park at Calverton (hence its name: EPCAL) on New York’s Long Island and links to the Town of Riverhead’s 65-acre...
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"...
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...
Canopied with deciduous trees for most of its 10.4 miles, the Larkin State Park Trail (a.k.a. Larkin Bridle Path) is primarily a wilderness trail, with wooded vistas, wetland views and sparse...
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 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...
Air Line State Park Trail winds for just over 55 miles from the northeast corner of Connecticut, where the state borders Massachusetts, down to East Hampton in the heart of the state. Over the state...
The Connecticut River Walk and Bikeway, which will one day run 21 miles along the river, currently has two open segments. The longest stretches 3.7 miles from the Chicopee town line to the South End...
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 Redstone Rail Trail is built on the former New York, New Haven & Hartford Armory Branch, which in turn is a former branch line of the New York & New England RR. Its name comes from the numerous...
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 Charter Oak Greenway is a paved, multi-use trail connecting parks with residential and commercial areas. The trail runs for 11 miles between Bolton and downtown Hartford, though there is currently...
Running north from the Yale University campus in New Haven through the heart of Connecticut, the multi-use Farmington Canal Heritage Trail, when completed will stretch uninterrupted more than 80 miles...
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"...
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 Hop River State Park Trail is one of Connecticut's longest rail-trails. Narrow cuts and a lush tree canopy make for enjoyable visits year-round. Near its western end is the Charter Oak...
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...
The delightful asphalt Middlebury Greenway winds 4.4 miles through the residential community of Middlebury, connecting businesses, parks and neighborhoods. The popular trail offers residents 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 EPCAL Alternative Transportation Path loops around the 2,900-acre Enterprise Park at Calverton (hence its name: EPCAL) on New York’s Long Island and links to the Town of Riverhead’s 65-acre...
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...
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 Kress Family Trail follows an old rail bed of the former Shepaug Railroad, which winds along the Shepaug River. The flat, 2.5-mile trail is popular with cross-country skiers and snowshoers in...
Hi All,
Per "Record Journal" Newspaper New Section of "Farmington Canal Heritage Rail Trail" (Curtiss St & Kane St) to Lazy Lane. Happy Trails, RVC (tn) "Zenith"
I had a great time riding this trail last Sunday. I started in Pomfret from the old railroad station parking lot on Railroad Street.
I rode 7.5 miles, then reached a very long section which was covered in rocks that were sharp edged, about 1 1/2inches on a side. I took a break and enjoyed the view over the wetland area there. I was just able to ride over that rocky section on my cross bike, but it was a rough and uncomfortable ride. It went on for around three miles!!
I'm curious to know why this one section is prepared so differently from the rest of the trail.
I rated the Air Line trail a 4 of 5 stars. When I previewed my review, it showed more like 15 stars. Why is that?
Was searching high and low for a long trail like this for long runs. Went here for the first time this past weekend and it completely surpassed any expectations I had. Everyone was super friendly! The views were amazing. Will be even more beautiful in the fall. Can't wait to keep running here and bringing my dog along as well!
I think this trail is fine for local people who want to get a little exercise and bike through town. But it's not a trail you drive to for a scenic ride and it's not good with kids.
We parked I guess midway, in area the Greenwyay's facebook page directs you to. In a few blocks it turns into a sidewalk with a lot of strip mall driveways. the other way, the trail petered out onto a residential street after a few blocks. By myself I might have followed it to see if it became a trail again. But I didn't want to bike on the busy sidewalk or on the street with my kid. Also, the hills are not long but they are steep and challenging for a kid who is still on a bike with 20" tires and no gears. So we gave up. Wish trail link would have a category up top that defines trails as scenic "destination" rides or "getting around" local rides. It would have saved us a lot of time.
The part that goes through Beacon Falls is about a half mile long and it goes along the river, yes, but on a sidewalk through a not particularly charming town. The part in Naugatuck is paved for about a mile through a park and then turns to dirt, not suitable for a road or hybrid bike at all. Neither section was really worth the time it took to take our bikes on an off the rack.
Hey, this is a well-maintained, wide asphalt path and fine for their community. As the description stated, it is "hillier and more winding than a typical rail-trail," so take that into consideration. I am spoiled by rail trails, but am glad I did it once, but would not travel an hour and half again. If you're in the area or within half and hour drive it's very fine.
This is a hybrid/mountain bike trail. Great riding experience.
This trail should not be advertised as an 8.5 mile trail for walking. The first section is paved and well maintained. After the paved path ends, you are hiking through tall grass and often you question whether this is really a path or if you are actually trespassing. It usually feels like you are trespassing and blazing your own trail. Eventually, my wife and I abandoned the path when we came upon River Road and a hole in the fence. It was not worth the hassle to try to keep blazing our own trail. The dead, decaying deer in the middle of the path sealed the deal for us. We found our own way back through Enterprise Park. If this "trail" is intended as a publicly owned and maintained walking path, then it is falsely advertised as such. The path is probably great for mountain bikes if you enjoy pedaling through tall grass. AVOID UNLESS YOU KNOW WHAT YOU ARE IN FOR.
I have been riding this trail several times each year and am never disappointed. From the Wassaic train station in Amenia to Millerton is 10 miles of farmland and woodland with spectacular views. Beautifully maintained and lightly traveled it attracts courteous hikers and bikers. Millerton has a couple of excellent places to grab a snack and on Saturday mornings there is a small farmer's market. I try other trails for variety but return to the HVT to recharge.
Today, we rode from Hopewell Junction to the Walk on the Hudson Bridge a perfect 26 miles. The trail is well maintained and wide enough for multiple use. It is shady and flat as a pancake except for the normal bridge crossing. Highly recommend
I rode from Farmington to Mass. three times , Cheshire to New Haven one time, and Cheshire to Southington twice. I rode Farmington River Trail to Simsbury via Farmington Canal Heritage Trail several times. I am getting excited waiting for the 9.1 mi connection between Southington and Farmington. It has been an enjoyable summer of 2017 riding. Yes I am a member and intend to be for a long time. Great job to all involved.
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