Explore the best rated trails in Cromwell, 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 53 trails covering 393 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 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...
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...
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 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 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 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...
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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...
It’s hard to pick a favorite season to experience the Hop River State Park Trail, set amid the dense forests of Eastern Connecticut. Sections of the 20-mile rail-trail dive through steep rock cuts...
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 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...
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...
Bookended by beaches and offering gorgeous vistas of Niantic Bay, the Niantic Bay Boardwalk is a must-do excursion in the small Connecticut village of Niantic, part of the larger Town of East Lyme....
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 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 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 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 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 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 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...
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 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 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 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 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 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 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...
It’s hard to pick a favorite season to experience the Hop River State Park Trail, set amid the dense forests of Eastern Connecticut. Sections of the 20-mile rail-trail dive through steep rock cuts...
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...
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 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....
Where a trolley once ran, now you can too on the south bank of the Mattabessett River. The electrified trolley shuttled passengers from Berlin to Middletown and beyond. The smooth blacktop and an easy...
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...
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 Westville Lake Community Trail offers a short, scenic excursion along the east bank of Westville Lake in Southbridge. Much of the crushed-stone pathway is under a lush tree canopy. Along the way,...
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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 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 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 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 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 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...
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...
It’s hard to pick a favorite season to experience the Hop River State Park Trail, set amid the dense forests of Eastern Connecticut. Sections of the 20-mile rail-trail dive through steep rock cuts...
Bookended by beaches and offering gorgeous vistas of Niantic Bay, the Niantic Bay Boardwalk is a must-do excursion in the small Connecticut village of Niantic, part of the larger Town of East Lyme....
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 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 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...
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...
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 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 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...
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 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 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 Westville Lake Community Trail offers a short, scenic excursion along the east bank of Westville Lake in Southbridge. Much of the crushed-stone pathway is under a lush tree canopy. Along the way,...
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 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....
This 5.8-mile trail is part of the planned East Coast Greenway, an off-road path that will eventually run from Calais, Maine, to Key West, Florida. The Moosup Valley State Park Trail will connect with...
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...
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...
Nearly perfectly flat - good compact ground - three nice bridges - very little other traffic.
We had two kids, 8 and 11, with medium bike skills - easy going here so was all fun and no hassle. We started in the middle (parking area) and went to each end and back. Total 6 miles, took 1 hr due to stops to view wildlife.
Only drawback: we wanted more miles !!
Trail is actually 2 miles now and its a great trail quick trail for beginners trying to get their exercise in. For me its easy trail to get a quick bike ride and keep in shape its my go to on a day i dont gave much time.
Beginning at the eastern point in Northampton, this is not well signposted. It connects with the western end of the Norwottuck trail heading west by turning right (turning left goes to the Manhan trail) at the T junction once you have gone through a tunnel having crossed the Connecticut River and crossed a couple of roads. It takes you to Florence / Leeds including the Look Memorial Park in Leeds. Heading west, having turned right onto this trail from the Norwottuck trail it goes behind a commercial building and seems to stop. At this point you come out between these buildings facing a road. Cross this road at the traffic lights and go through the Stop and Shop parking lot to the left of the supermarket building. There is an official gap in the fence where you can join the rail trail. It is not marked. Follow the trail to the right. It is a little bumpy with roots to start with but is a nice scenic paved trail.
Generally this trail is in good condition, paved all the way, few lumps and bumps with tree roots etc. The bit that isn't marked well is where it joins the Norwottuck trail in Northampton. If you start on the Norwottuck trail heading west this trail begins by turning left once you have gone through a tunnel having crossed the Connecticut River and crossed a couple of roads. The other direction - that also is not marked - takes you to the Northampton bike path to Florence / Leeds - more about that in the respective review for that bike path. The Manhan trail crosses over Main Street right by the railroad station and takes you through Northampton - a good interesting ride on to Easthampton and Southampton where it dead ends.
Started at the western trailhead on Kettletown Road. Nothing but a single track -- including a climb down to Jeremy Swamp Road to cross and then a climb up the other side. Clearly, decades ago there was a rail bridge here, but it's gone. For a while, the trail is fine, but then another problem on this leg is that the trail becomes virtual impassible for bicycles -- you are trying to ride up a creek bed full of grapefruit sized rocks.
East of Strongtown/CT 188, there is a mix of beautiful gravel surface through the woods with some low spots/mud (we've had some rain). The route is wooded and quiet -- really nice ride. You will likely encounter horses (I passed a single rider and a pair on this ride). Etiquette is to be very careful and slow -- give them a shout as to which side they'd prefer you pass on. Also a lot of wetland. If you're moving fast on a bike, it's OK, but walking you're going to be dealing with A LOT of mosquitoes.
Summary -- with some investment this could be one of the prettiest rides in CT, but there are some real rough/muddy spots.
I can see where this could be a beautiful autumn ride. Will give it a few more tries this season.
The foot bridge and immediate surrounding view very pretty is the highlight. The walk is flat and hard to find. You go under a road with concrete supports sprayed with a lot of graffiti and then leave a crushed gravel path for a concrete walkway over a marsh. The marsh is a habitat for egrets. The path was more for bicyclists, who were impatient about walkers on trail. dismounting for walkers. We skipped the concrete path due to heat and people on bikes
A beautiful trail, level riding and scenic. Great rewards at the end, places to stop , eat and shop. Can park and lock your bike at trails end. Look forward to it’s completion.
This section has been open for a year or two now (June 2020) and is excellent condition all along following the power lines. Approximately 4 miles long end to end with nice smooth black top ideal for cycling, now also attracting walkers, skaters etc. There are footpaths into the adjacent woods.
There is a car park at the Wayland end easily accessible from the intersection of rte 126 and 27. At the eastern end the last access point is at Church Street, Weston. Further east it just dead ends at a decrepit bridge.
Very little elevation change. New section south from Wassaic station is very nicely done, but disappointingly short. Beautiful ride north from the station to Millerton.
This trail is great for beginners, especially for my kids who just started riding without training wheels. There are a few moderate hills that may be difficult for single-speed bikes. Overall great experience with potential offshoots to Haley Farm, Bluff Point, and more.
Parked in new haven and had a great ride to Cheshire. A lot of streets to cross at the beginning and end but still nice in new haven. Once things open up it is a perfect ride.
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