Explore the best rated trails in East Hampton, CT. Whether you're looking for an easy walking trail or a bike trail like the Windsor River Trail and Niantic Bay Boardwalk. With more than 54 trails covering 418 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.
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...
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 Quinebaug River Trail exists in two segments in northwest Connecticut. The northern section parallels Park Road and Tracy Road for about 2 miles in an industrial section of Putnam with few trail...
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 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 Massachusetts Central Railroad was destroyed by a hurricane in 1938, but the 104-mile corridor is being reborn as a cross-state rail-trail. Currently, nearly 50 miles from Boston to Northampton...
At the turn of the 20th century, Groton & Stonington Railway Company began to move passengers between Groton to Mystic via electric trolleys. But in 25 years, the line had been discontinued due to...
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 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 Bissell name looms large in this part of New England, and has been immortalized in multiple ways, including the Bissell Ferry, the Bissell Memorial Bridge and now, the Captain John Bissell trail,...
The Manhan Rail Trail, well integrated into the local communities it serves, offers a pleasant ride or stroll. It conveniently weaves together parks, community points of interest, neighborhoods, and...
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...
Imagine a wealthy 19th-century textile mill owner building an 8-mile railroad to get coal to his plant or products to market, and then adding accommodations to carry vacationers to beach resorts or...
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...
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...
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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...
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...
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,...
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...
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 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 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 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 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...
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The Rockville Spur, a section of Vernon Rails-to-Trails, is a stone-dust rail-trail stretching 4.2 miles into the heart of historical Rockville. The trail begins on Warren Avenue in Vernon, but you’ll...
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 Manhan Rail Trail, well integrated into the local communities it serves, offers a pleasant ride or stroll. It conveniently weaves together parks, community points of interest, neighborhoods, and...
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...
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 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 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 Quinebaug Valley Rail Trail runs on the corridor once occupied by the Southbridge & Blackstone line of the Providence & Worcester Railroad, transforming a corridor once designed to link rural...
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...
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 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 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 Bissell name looms large in this part of New England, and has been immortalized in multiple ways, including the Bissell Ferry, the Bissell Memorial Bridge and now, the Captain John Bissell trail,...
The Southern New England Trunk Line Trail (aka the "SNETT") was designated as a National Recreation Trail in 1994. It is built upon a segment of the former right-of-way of the New Haven Railroad's...
The Quinebaug River Trail exists in two segments in northwest Connecticut. The northern section parallels Park Road and Tracy Road for about 2 miles in an industrial section of Putnam with few trail...
The overall goal of the Grand Trunk Trail in south-central Massachusetts is to connect the communities of Brimfield, Sturbridge, and Southbridge by trail. Currently, two sections of the trail are...
Imagine a wealthy 19th-century textile mill owner building an 8-mile railroad to get coal to his plant or products to market, and then adding accommodations to carry vacationers to beach resorts or...
The Qunnipiac Linear Trail is an easy multipurpose path in Wallingford, Connecticut. The trail skirts Community Lake while traveling a heavily wooded corridor along the Quinnipiac River. It is one of...
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 Washington Secondary Bike Path offers just over 19 miles of paved trail from Cranston (Providence’s southwestern neighbor) to Coventry. The rail-trail, Rhode Island’s longest, follows the former...
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...
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 North Shore Rail Trail, formerly known as the Rails to Trails Recreational Path, is a 10-mile multi-use recreational path and runs along the former Wading River railway corridor in Brookhaven—the...
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 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...
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 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 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 Southern New England Trunk Line Trail (aka the "SNETT") was designated as a National Recreation Trail in 1994. It is built upon a segment of the former right-of-way of the New Haven Railroad's...
The Putnam River Trail extends between Arch Street in the Putnam District and Providence Street to the south. The trail follows the east bank of the Quinebaug River between the river and Kennedy...
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 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 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 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 Quinebaug Valley Rail Trail runs on the corridor once occupied by the Southbridge & Blackstone line of the Providence & Worcester Railroad, transforming a corridor once designed to link rural...
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...
My wife & I have ridden this trail a number of times in the last month. It is scenic, well shaded, uncrowded, relatively smooth for any bike with easy road crossings. There's ample parking at Mackey's in Willimantic if you start at the eastern end. The first mile or so from Mackey's is a bit rough and there's a small road section but then the entire rest of the trail is excellent. One of my wife's favorites. Note: we have been riding this on our E Bikes.
I ride a lot of rails trails and this frankly did not blow me away. There are some great sections with great canopy and nature but there's miles that feels like a glorified sidewalk next to traffic. A couple very large cracks and sections with bad pavement in the New Haven area. You'd think that would be the most maintained section but I guess not.
I was glad to find this trail; I biked the Oakham-Rutland section. Traveling from Oakham to Rutland, I am estimating the trail is 95% gradual uphill, 3% challenging uphill, 1% level, and 1% downhill. Would you prefer biking uphill or downhill on the return trip? The trail is primarily stone dust with a few small rocks and a very brief section of gravel. Perhaps a mountain bike would be preferable, but my hybrid bike was fine.
Cycled the SNETT 28May2022 from Thompson CT to Franklin MA. 22 miles.
Summary: CT state line to the end of Douglas State Forest good - 5 *, last 2.5 miles in Franklin good 5*. The rest - don't bother as of May 2022 1*
The trail in Thompson CT is in fact the CT Airline trail that directly rolls into MA as the SNETT.
This section through to the end of Douglas State park is a really nice ride west to east on hard packed gravel, slightly uphill with some picturesque settings. This end of the trail can be ridden on a gravel bike. If you intend to ride further make sure that you have a mountain bike.
As you head out of Douglas State Park, it starts getting messy. 1/2 inches of rain the previous day and we're into the mud. Now a gravel bike doesn't cut it, and that's before the sand, rocks and stones. You'll need that mountain bike, determination and patience. There are lots of better places to go mountain biking than here!
At mile 11 the soggy muddy track dumps you onto the hard shoulder of rte146 just outside Millville MA. Good luck! If you are going east to west, your chances of finding this tiny on ramp at the edge of rte 146 are close to zero as is nearby parking.
Millville to Blackstone MA is on road, no sign posts, no directions and Google maps really doesn't cut it. You pick up the SNETT in Blackstone near a CVS. Yes....riiiiiight. Nope not happening. Google maps are not accurate here. Spent 1/4 hour checking out the back streets of Blackstone. Good luck.... do not rely on Google maps too much for trail directions.
Picked up the trail again on Farm Street by the lake and landfill. A pathetic single track trail, between 2 lakes, boggy, rocks across the whole trail and you need the mountain bike to get through the mud. Avoid.
1 mile later go through an underpass of rte 126, trail is closed. No warning, no diversion, tough. Another reason to avoid. Scramble up the embankment to rte 126. Road trip past South Elementary School to Franklin - about 1.5 miles. Rejoin the SNETT (yes, signposted at last!) for the last 2.5 miles, a mixture of paved and hard packed dirt - rideable with most bikes - maybe not with a true road bike. This bit is definitely worth riding.
I began at the trail head - bit bumpy for the first mile and a side trail has been rerouted because of the wet mucky ground. Once you pass that it’s clear sailing until… the 3 mile point and the trail is closed. Logging equipment and logs block the trail. ¿
The first couple of miles are paved, which makes up for the lack of scenery. But once the pavement ends, for all intents and purposes, so does the path. Between the mud, the rocks and the fallen trees, I spent more time walking my bike than riding it! And that's not even taking the horseflies into account. Not to mention the frighteningly steep drop-offs. How dare they call this catastrophe a bike path!
For reasons I won't get into, I've long despised Connecticut's Route 14 corridor (Moosup, Danielson, Dayville, Plainfield, et al). This malevolent excuse for a trail gives me one more reason to do so.
My wife and I rode our recumbent trikes on the entirety of this trail on a Saturday evening. For the most part, we encountered only walkers. And based on the surface condition of the trail, I understand why. The pavement has deteriorated and is full of root-bumps and small dips. It was a very rough ride.
I would recommend this trail for walkers, joggers, or cyclists if you've got a bike/trike with a suspension. The bulk of the trail is on the old towpath between the river and the canal, so other than the north and south ends, you are separated by water from the rest of the world. This makes for a quiet, relaxing, and scenic trek. The northern terminus near the parking lot, which also forms a "T" with the CT 190 bridge, and the southern terminus by the renovated mill building are new and in great shape. All we need now is for Connecticut to resurface the original portion... even stone dust would be better than the broken pavement.
I went here on a beautiful Sunday afternoon. What a lovely place! This is a paved trail that follows the river and has a nice playground and picnic area at one end. There are various sculptures related to Abraham Lincoln along the way. It was very relaxing to stroll along the water. The views of the bridges and the Hartford skyline are stunning. Will definitely return!
I started This trail in downtown Derby in May 2022. They are doing some construction in the area where they say you can park. Go on a Sunday and park in the City Hall parking lot. Beside the parking and the tons of walker on the path is not bad.
Trail is nice for the size, well paved but hills. You can park on the back side of Maggie's and there are other places to park along the way.
On e Bikes; trail to north from Windham generally passable but long wet areas (eventually turned around) and trail a bit rougher than going south from Willimantic. The south trail is in much better shape and had inviting scenery with streams, farms and wetlands/lakes + virtually no wet areas on trail. Went to RT 87 (about 8 miles) from Willimantic. Plan to do this again and go further.
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