Find the top rated trails in Waterbury, 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.
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Note: Per the State of Connecticut's website, the trail is open from dawn to dusk March 1–November 30." The 4.5-mile Windsor Locks Canal Trail follows the Connecticut River and the Windsor Locks...
The Dutchess Rail Trail is a local treasure in the Hudson Valley region of New York, and for good reason: the 13-mile trail runs through what seems like a perpetually green landscape of dense tree...
The Old Croton Aqueduct State Historic Park follows the route of the Old Croton Aqueduct, which carried water to New York City from 1842 to 1955. Most of the structure lies beneath the trail and has...
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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 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...
Owned by the Metro-North Railroad, the Maybrook Trailway starts at the Connecticut state line in Farringtons Park, and spans 5 miles into the town of Brewster. The trail follows what was once part 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...
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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...
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 final passenger cars of the Putnam Division of the New York Central Railroad ran in 1958, but the rail line that so influenced development of this area still sparks nostalgia. The "Old Put"...
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 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 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 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...
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 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 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 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 Dutchess Rail Trail is a local treasure in the Hudson Valley region of New York, and for good reason: the 13-mile trail runs through what seems like a perpetually green landscape of dense tree...
The Briarcliff-Peekskill Trailway is a 12-mile linear park that runs from the town of Ossining north to Westchester County's Blue Mountain Reservation in Peekskill. The trail is built on land...
The Old Croton Aqueduct State Historic Park follows the route of the Old Croton Aqueduct, which carried water to New York City from 1842 to 1955. Most of the structure lies beneath the trail and has...
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 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 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 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 Kings Park Hike & Bike Trail runs for 1.5 miles between Old Dock Road at Church Street in Kings Park and Nissequogue River State Park. The trail is a town of Smithtown park and follows an...
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...
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 Kennedy Trail begins at the northwest corner of the 68-acre campus of John F. Kennedy Catholic High School in Somers. The town, which sits 30 miles from White Plains and 55 miles from New York...
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 Klara Sauer Trail (formerly known as the Beacon Riverside Trail) runs for 1 mile along the Hudson River on the west side of New York's village of Beacon. The trail occupies the same corridor as...
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...
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 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 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 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...
Located in the mid-Hudson Valley is a remarkable trail that is picturesque and family friendly. This flat, paved Hudson Valley Trail stretches nearly 4 miles through hardwood forests, over Black Creek...
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 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 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 Kennedy Trail begins at the northwest corner of the 68-acre campus of John F. Kennedy Catholic High School in Somers. The town, which sits 30 miles from White Plains and 55 miles from New York...
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 final passenger cars of the Putnam Division of the New York Central Railroad ran in 1958, but the rail line that so influenced development of this area still sparks nostalgia. The "Old Put"...
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...
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 Briarcliff-Peekskill Trailway is a 12-mile linear park that runs from the town of Ossining north to Westchester County's Blue Mountain Reservation in Peekskill. The trail is built on land...
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 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 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 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 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...
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 Quarry Trail is currently a 600-foot long unimproved strip of land along what is known as Quarry Road in the Village of Hastings-on-Hudson, NY. The trail links Old Croton Aqueduct State Historic...
The North County Trailway is the longest of the four connected rail-trails breathing new life into the former New York Central Railroad's Putnam Division line. The "Old Put" provided passenger and...
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...
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 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...
It has been reported that a large bear was seen on the trail section between Hop River Rd. and Parker Bridge Rd. in Columbia.
Tried to post a review but censors refused to post it.Let's see if they allow this post.Ran here in early August at 6AM on a cool,humid morning.Trail well maintained.Started at Tony Williams Park.Encountered group of people walking trail who had dumbbells and appeared questionable.Same people were eyeing my car when I returned to Williams Park.This may be a very isolated incident but is there any police presence on trail.Should not have experienced this at 6AM.For the safety of other trail users,you censors need this to be posted.
The North County Trail is suffering from serious neglect. It used to be a well maintained, smooth riding experience. It is now in danger of becoming a Civil War era corduroy road. There are many areas that are in desperate need of re-paving. There is also a section that was eroded during Super Storm Sandy and has not been repaired. It's a shame that what was once a terrific trail has been allowed to degrade so much.
This trail has a little bit of everything ..... asphalt, grass, hard packed dirt or gravel. We started on the North end at Pepper went south and was for the most part going on a slight downhill 80% of the way to The Trumbull trail end. It was for the most part lovely. Often very wide and smooth. I would go the opposite way as Linda and I always prefer to glide back to the car.
Hi All,
They recently put the steel in place for the bridge over CT RT 6 in Farmington for Farmington Canal Rail Trail (FCRT). The section maybe in the maybe done in the fall of 2017? It should be complete rather fast! I scouted it out via car lots of this section done.
Trails, Russ C (tn) "Zenith"
Hi All,
Someone asked where is H2~O??
The WATER FOUNTAIN is just due south of jct Southwick Rail Trail & Sam West Rd. Approximately 5.16 Miles North of the CT/MA Border. The fountain is probably seasonal. Nice Ride From CT Border to Main St Westfield, MA (Shop & Shop) Great Day & Good Time. Execellent Bike Pump & Repair Station at CT Quarry Rd & Phelps Rd Lot. Happy Trails, Russ C (tn) "Zenith"
We had two cars, and wanted to ride one way so we left one car behind the First Congregational Church 359 US 6, Andover, CT. The second car we parked at the trailhead 175 Colonial Rd, Manchester, CT where there is a dedicated parking lot. By car it was 15 minutes driving time one way between locations. From our start point we crossed RT 6 in front of the church to pick up the trail and then rode to the right heading west. The first 5 miles were a definite uphill grade, around mile 6 it became a downhill grade all the way to Manchester. Total distance between the two locations approximately 12 miles. Considering the trail is mostly hard packed dirt it was very well maintained, wider in some areas than others with a few road crossings. The scenery was mostly rocks that had been blasted through back when the railroad was built with a lot of ferns and greenery, but never saw the Hop River. There were mostly bikers on the trail, and everyone was very friendly. Other than the uphill grade for 5 miles it was a very pleasant ride. If you're looking for a nearby place to stay I highly recommended the Daniel Rust House in Coventry which was only 12 minutes from the church by car.
Started in Hamdon and road to Southington. Round trip was 28.04 miles. Rented bicycles from Cheshire bike shop which was all of 50 feet from trail. Trail was nicely paved the entire way except for a very short detour.
Once you get in the main trail, it's a nice, easy ride. But I picked up some kind of metal shard in my tire, and I suspect it was on the access trail that starts on Boardman.
Beautiful ride along the river BUT you better have a very soft seat to absorb the rough surface!!
This is a nice place to stretch one's legs for about five miles. The southern end (just over Boardman Bridge from Route 7), with limited parking, runs through a town park for about 1.5 miles; the northern portion, ending at Gaylordsville, is just walking along the Housatonic on River Road, one of the few remaining dirt roads in the area. There is more parking at the park's main entrance off of River Road, about 1.5 miles north of Boardman Bridge.
If you like a flat trail in quiet woods and don't mind a few cars coming along, this is a pleasant way to spend a couple of hours. "There and back again" is about ten miles.
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