Explore the best rated trails in Portland, CT. Whether you're looking for an easy walking trail or a bike trail like the Niantic Bay Boardwalk and Norwalk River Valley Trail. With more than 47 trails covering 383 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 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 40 miles from Boston to Northampton...
Paralleling the Connecticut and Massachusetts borders, which lie only a few miles away, the Harlem Valley Rail Trail is a beautiful paved wooded pathway along the former New York & Harlem Railroad...
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 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 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...
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 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...
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...
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...
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 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...
Running alongside both the Housatonic and Naugatuck Rivers, the Derby Greenway demonstrates a seamless integration of Connecticut’s natural river systems and parks with man-made interventions of the...
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 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...
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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...
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...
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 Locks. Due...
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,...
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...
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 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 40 miles from Boston to Northampton...
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,...
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...
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...
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...
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 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 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 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 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...
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 Locks. Due...
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 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...
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...
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 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...
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 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 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...
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...
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 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...
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 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 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 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 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 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 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 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...
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...
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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...
Paralleling the Connecticut and Massachusetts borders, which lie only a few miles away, the Harlem Valley Rail Trail is a beautiful paved wooded pathway along the former New York & Harlem Railroad...
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 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 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...
Running alongside both the Housatonic and Naugatuck Rivers, the Derby Greenway demonstrates a seamless integration of Connecticut’s natural river systems and parks with man-made interventions of the...
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...
We were told once we arrived on the trail, that it was not complete. We discovered that we had to share a gravel road that was not on the rail portion. The trail to the North was in process of being worked on and not at all passable. Some notice needs to be posted saying Trail is under construction or sharing roads with cars is noted. The Map looks Identical to the Cape Cod trail which was excellent .....no indication that the Harlem trail was not complete
Contact with the Hop River design team has developed some news on the last remaining undeveloped area on the Hop River Trail. The section on the Windham side of the Willimantic River is under construction. A late summer opening is anticipated. This work will allow traffic over the Willimantic River from the current end at Mackey's Ag. store. A parking area is also part of the work.
The Trail from the Columbia town line to Kings Road (the current end of the developed trial) will be under design late this year. Bids, construction and all that stuff pushes the completion into 2021.
So late this summer, with a MT bike, you will be able to cross the river from Windham and follow the unimproved rail bed to Flanders Road, turn right to Kings Road and get back on the improved trail, That's less than a mile of off trail and local road.
I love to walk the trail and have since 1971, the cross over on Whitney Ave in Trumbull is Terrifying, The cars cannot see any one passing the road way until they are in the roadway. The line of sight is completely obscured by vegetation and the small sign in the middle of the Street??? I have seen people run right across the road with out even slowing down prior to or while crossing Whitney Ave. I personally saw a woman hit the side of a car as she could not stop running in time to avoid the car. This section is an accident waiting to happen. Whitney Ave. crossing needs to be safer for both motorist and trail user.
Paved path of just about 8.5 miles (all off the regular roadways) provides a great pathway for all skill levels. Beginners can take a leisurely ride with gradual inclines or more experienced riders can challenge themselves with speed and cadence. The path is completely free of roadway dangers as it is only open to walkers, bikers, skaters, etc. It has quite a bit of shady areas to stay out of direct sun due to its location near the woods. Some nice natural scenery. Start/end point located near Veteran Memorial and Isaac Dog Park for other points of interest.
In April 2018 the Windham Town Council approved $1,300,000 for rehabilitation on the Willimantic River bridge behind Mackeys. This would include 800 feet of trail. It was put out for bids due on July 26th. I haven't seen any work yet. There is still the bridge over the Hop River which looks to be in terrible shape and may never be repaired.
Quick update that a stretch of trail less than one mile between Cornwall Av. and West Main St. in Cheshire is now officially opened, avoiding a detour onto Willow St. There is now a continuous, paved, off-road stretch of trail some 25 miles from Temple St. in downtown New Haven to Lazy Lane in Southington.
I just road the Airline Trail across the Willimantic River and then toward the newer ending at Mackie's Ag. Store near the Columbia town line. It was in fine shape. However, what I was looking for is evidence that the work on the Willimantic River bridge was started. I found nothing underway. I road to the easterly end of the Hop River Trail hoping that it was starting at that end. No such luck. Does anyone out there have any information on when this section will be started?
This is a really nice trail, most of it is under a canopy of trees, nice scenic spots on the river if you want to stop for lunch. I took my hybrid the full 40 miles out and back. Except for maybe a half mile of stones and gravel in Bolton Notch where a mountain bike would be better, the rest was nice hard pack dirt and pulverized stone. I saw thin tire street bikes on this trail as well. There are very long stretches on this trail where you don't cross any roads, and except for maybe one exception, most of the crossings have little traffic and are side roads. I also like the width of the trail. Two thirds of the trail is very wide. After Andover it gets a bit more narrow but there were also fewer people on the trail towards Willimantic. The only down side is that the trail terminus in Willimantic is pretty anticlimactic. You come to a road that that's it. No parking lot or grassy area, just a road and you know its over unless you want to continue on-road biking to Willimantic.
As of September 8th 2018 there is only one thing holding back the expansion of the Charter Oak Trail from Porter Street to the Hop River Trail in Bolton, the bridge over Camp Meeting Road. It should be the completion of just a few details that will allow this section to be open to the public: accepting the last bridges and some land scaping work. Once the bureaucracy is done, riders will be able to connect from East Hartford to Bolton and beyond. That's about 15 miles of the Charter Oak Trail and 20 miles of the Hop River Trail that will be connected, finally. Of note, there are two more bridges in Windham and Columbia at the eastern end of the Hop River Trail that are going to bid this fall. Once done, it will open a trail from the Hartford area to Pomfret CT. Be patient. What's another year or so to get all these trails linked.
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