Explore the best rated trails in Middletown, 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 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 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 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 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 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...
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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 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 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...
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 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 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...
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...
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 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...
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 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 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,...
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 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...
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...
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...
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...
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....
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 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 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 Maybrook Trailway is a paved multiuse trail stretching across Putnam and Dutchess counties in New York state. The trail, which is owned and was built by Metro North Rail, occupies the former...
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 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...
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 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 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...
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 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 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 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...
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 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...
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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 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 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...
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 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...
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...
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 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 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...
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 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...
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 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...
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 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...
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 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 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 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...
The day that I rode this trail was a beautiful Spring day and there were various other riders, walkers, runners and, in Northampton, people going for stroll. It is a well maintained trail, not too long, plenty of things to see and places to relax. Part of the trail is rural feeling, but other parts are located right near downtown. A nice mix.
Our inaugural ride on the Maybrook trailway today. Rode from Lake Tonetta (Town of Southeast Park) in Brewster to Whaley Lake in Patterson and back, about 25 miles.
A real treat to ride on this brand-new trail, part of the Empire State system. The route out from Brewster starts flat and then becomes a very gradual uphill grade to Whaley Lake. Not really anything to be concerned about…very doable, and we enjoyed the gradual downhill for the second half of the ride. The route is very open – since the trail parallels the old (still there) tracks, there’s a feeling of openness – bright sun the entire way. The sections through Lake Tonetta, the “Great Swamp,” and the “Ice Pond” are very picturesque, with occasional view of hills in the distance along with the lake views. The best part is a 2 mile section along Whaley Lake – beautiful views of the lake and some very nice houses on the opposite shore. All in all, a great new trail – and in Fall this is going to be spectacular. A few notes: bathrooms available at Southeast Town Park (start of trail, adjacent to Lake Tonetta). I didn’t see any other bathrooms along the route, haven’t yet explored on-road possibilities e.g. nearby stores at the crossings. Bring sunscreen – very open, lots of sun. The route continues to Hopewell Junction where it picks up another section of the Empire State Trail – lots of info on the web.
DO NOT park at Maggie McFly’s. Lots of signs and I called. They directed me to other nearby commuter lots and parks
Nice trail well maintained but kinda boring. I had done another longer trail in the area and this was a bonus. It’s great that the locals have this amenity but it’s not a destination ride.
Rode the northern part of this trail on 4/26/21 from Hopewell Junction to Holmes as part of my ride from New Paltz. Trail was scenic and smooth with few and easy road crossings. I imagine because of the width of the railroad tracks and the trail making this pretty much in the sun for most of the ride. Just keep in mind it’s not fully recorded in red on the trail map. Great trail if you want a great distance ride.
I was looking for a relatively easy trail near home to start off the season with and I found it! From the beautiful lakes along the way to the running water area (see pictures!) this was a lovely trail and I enjoyed it. I parked on Mill Road in Dudley; the parking area was easy to find! When deciding which way to go just don’t go toward the bench. Go instead toward and through/beyond the yellow gate instead. Only go the other way if you’re curious to see the rail ties discussed in another post on this site. Please know too that, even when heading through the yellow gate, way on the other side from about a mile to the end are some rocks that make traveling with the bike a real challenge (four stars for this reason). It’s worth the difficulty though if you’d like to go to the mall area at the end of the trail since you may want to eat/use the bathroom and then head back (there’s a Big Y, McDonald’s, etc.). Again, lovely trail and the middle area with the lakes makes it all worth it!
I was looking for a relatively easy trail near home to start off the season with and I found it! From the beautiful lakes along the way to the running water area (see pictures!) this was a lovely trail and I enjoyed it. I parked on Mill Road in Dudley; the parking area was easy to find! When deciding which way to go just don’t go toward the bench. Go instead toward and through/beyond the yellow gate instead. Only go the other way if you’re curious to see the rail ties discussed in another post on this site. Please know too that, even when heading through the yellow gate, way on the other side from about a mile to the end are some rocks that make traveling with the bike a real challenge (four stars for this reason). It’s worth the difficulty though if you’d like to go to the mall area at the end of the trail since you may want to eat/use the bathroom and then head back (there’s a Big Y, McDonald’s, etc.). Again, lovely trail and the middle area with the lakes makes it all worth it!
The trail is great! My husband & I rode it thus weekend and discovered that they have recently completed it north from Millerton so both sections are now connected!
This is a nice even, smooth trail, mostly flat and very easy to skate. Just a few small hills, I can usually build enough momentum to coast most of the way up. It's not very long so it's a nice stop if I don't have a lot of time. Can be crowded in the evenings, after work and school, lots of people walking their dogs.
Rode the Maybrook trail for the first time this morning starting in Brewster, going north. Lots of gradual uphill going north which made the return trip easier. Beautiful natural scenery.
Road this entire trail this past week as an out-and-back from Brewster. It's in perfect condition with limited road crossings.
As previous comments noted it's not exactly flat. Signage states you cross the Appalachian Mountains (known as the Taconics in this area)!
In Brewster I parked in Markel Memorial Park which is closer to the southern end than Southeast Town Park. It has a short road hop to an on-ramp to the Trailway.
If you want to take the older section to Connecticut the new Trailway dead ends at Peaceable Hill Rd with steps down to the road. There is an unmarked road section leading to another flight of steps on East Main Street (bypassing an unusable trestle). Note that the trail ends about a mile south of the steps where the trail is being reconstructed (no signs of activity).
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