Find the top rated trails in Portland, 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 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...
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...
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 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 Washington Secondary Bike Path actually comprises four trails along an old Hartford, Providence, & Fishkill Railroad corridor. Together, the Cranston Bike Path, Warwick Bike Path, West Warwick...
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,...
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...
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...
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...
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 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 Farmington River Trail is built upon the former Central New England Railroad corridor and runs between the Farmington Canal Heritage Trail near Tunxis Meade Park and the Simsbury town line. A...
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 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...
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...
As of January 2012 the Quinebaug River Trail has two segments. The southern segment follows the course of the Quinebaug River in Danielson, beginning at the intersection of Palmer Street and Prospect...
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 Farmington River Trail is built upon the former Central New England Railroad corridor and runs between the Farmington Canal Heritage Trail near Tunxis Meade Park and the Simsbury town line. A...
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 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 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...
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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 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 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...
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...
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 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 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 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...
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...
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 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...
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 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...
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...
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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...
Grand Trunk Trail is part of a larger trail network, the Titanic Rail Trail, which will stretch more than 60 miles through south-central Massachusetts and the northeastern corner of Connecticut along...
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 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 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 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 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...
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...
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...
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...
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...
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...
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...
As of January 2012 the Quinebaug River Trail has two segments. The southern segment follows the course of the Quinebaug River in Danielson, beginning at the intersection of Palmer Street and Prospect...
Grand Trunk Trail is part of a larger trail network, the Titanic Rail Trail, which will stretch more than 60 miles through south-central Massachusetts and the northeastern corner of Connecticut along...
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,...
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 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...
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 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 last 1/2 mile of final surfacing from the Route 6 bridges to King Road is done, and a nice job too!
Windham hopes to have the bridge over the Willimantic River and that section out to bid in the spring of 2018.
beautiful , shady, flat trail. plenty of parking spots.
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?
The 0.65 mi. extension of the trail from Curtis St. to Lazy Lane is now open although the connection from the old end of the trail at Curtis St. still requires crossing a tricky intersection. Lazy Lane is now the best place to start in Southington as there is a big new parking lot and that location provides easy access to and from Rt. 10 off the I-84 Queen Street exit. It is now 8.5 miles of continuous very well paved and completely off road trail from Lazy Lane in Southington to Rt.68 (West Main St.) in Cheshire. If you take the short .75 mile ride down Willow St. off of West Main St. to the Cornwall St. entrance of the trail you can get back off road very quickly. I rode the first .75 mile section of the trail south from Cornwall St. to Higgins Road to make it a nice 10 mile one way trek from Lazy Lane but I was surprised to see how many cracks there were on this part of the trail. They were all pretty much filled in but since they are very frequent and extend completely across the trail it was not very comfortable riding for a road bike. In contrast I don't recall seeing a single divot on the 8.5 mile section from Lazy Lane to Rt. 68. Another interesting aspect of this 10 mile section of the trail is that the first 4 miles headed south provides no shade at all in the September mid-afternoon and then the next 6 miles starting at about Rt. 322 is almost completely shaded. On a nice mid-70's afternoon that lack of shade in the beginning was actually very comfortable but I imagine it is kind of hot on a mid-summer afternoon. The contrast between the 2 sections of this 10 mile route makes for a great ride as those changes also parallel the route starting urban and turning almost rural by route end.
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 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.
TrailLink is a free service provided by Rails-to-Trails Conservancy (a non-profit) and we need your support!
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