Find the top rated trails in Watertown, 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 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...
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...
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 paved Charter Oak Greenway rolls more than 13 miles through the tree-covered hills and eastern suburbs of Hartford before crossing the Connecticut River and ending in the capital’s downtown. At...
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"...
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...
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...
Built in 1888 to link New York and New England to the coal beds of Pennsylvania and the West, the steel cantilever truss Poughkeepsie-Highland Railroad Bridge was the longest bridge in the world for a...
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 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 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...
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...
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 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 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...
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 William R. Steinhaus 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...
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...
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 Bronx River Greenway will one day stretch 23 miles along the river through New York's Westchester and Bronx counties. Currently, 18 miles of the trail are complete in disconnected segments largely...
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...
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...
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...
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 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 William R. Steinhaus 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...
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 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 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"...
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...
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 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 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 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...
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 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 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 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...
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 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 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...
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 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 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...
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...
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...
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 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 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,...
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 William R. Steinhaus 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...
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 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 Bronx River Greenway will one day stretch 23 miles along the river through New York's Westchester and Bronx counties. Currently, 18 miles of the trail are complete in disconnected segments largely...
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...
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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...
Just an hour north of New York City, the Timp-Torne Trail offers a scenic hike through Bear Mountain and Harriman State Parks with panoramic vistas of the Hudson River. The rugged blue-blazed trail...
Built in 1888 to link New York and New England to the coal beds of Pennsylvania and the West, the steel cantilever truss Poughkeepsie-Highland Railroad Bridge was the longest bridge in the world for a...
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...
No meter parking along Kimball Ave before Palmer Rd.
To avoid getting lost trying to connect to the bike path after passing the Scarsdales Train Station: exit at the station go north on East Pkwy; Rt on Crane Rd; Lf on Fox Meadows Rd (after Fenimore Rd) it changes to Walworth Ave and Lf on Greenacres Ave. The 2nd entrance to the trail is about 1/5 mile on the right.
There are restrooms when you reach the Kensico Dam.
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.
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.
I am lucky emough to live 1/2 mi from the Farmington Valley Trail and use it quite frequently along with a few of my friends.
I used to ride my horse along this route before it was scheduled for paving for a rail trail. Back then very FEW people used it. Mostly young motorcross kids and horseback riders.
Since it has been paved - horses are now NOT ALLOWED!! (Too bad for us); but as I have moved away from horse riding to personal trail use I am SO HAPPY that I have this wonderful gift in my back yard. There are many many miles and it spans on into southern massachusetts as well.
The trail itself is wonderful; paved, stripe’d and mowed in my area. I have ridden into Mass and south to Simsbury. Before my section was paved I had to load my bike and drive to Simsbury and unload, reload etc. Now, I just hope onto bike (or walk) and go for as long or far as I choose. The scenery is mostly rural, treed and very few homes are seen unless you are crossing streets. I know there are black bears near our home (area) but have not SEEN one ON the trail (daytime use).
It is SUCH a marvelous thing - and I see dozens and dozens of folks biking, walking, & rollerblading. Its a joy to be out in nature!!
Labor Day weekend, 2018
I had a hard time finding the entrance at Swamp Road, it is only marked “No authorized vehicles” and, more ominously, “Police are monitoring illegal activities.” My 7-yr-old son was alarmed and frightened by the signs and the broken down structures, rusty dumped machines and the lack of a path about 500 feet in. Instead it’s a broad overgrown cement yard - too broad to find the narrow throughway to continue south. We rode around a bit on the broken glass and shards, and left feeling unsafe.
I will probably return without him to try again, as I would really like to find a path off the street to get to Trumbull, but I can’t recommend this segment above Pepper.
Well-maintained, great bike ride. Lots of really cool stops along the way. Beautiful views on the trail north of Hartford.
Summer 2018: They finished paving over 8 miles. It’s a wonderful way to get fresh air and exercise with your kids without worrying about traffic. Pick up trail at eastern driveway at Veterans Memorial Park/Isaac Dog Park in Calverton. Bring water—or cut across Route 25 at Stony Brook incubator site (near intersection of 25 & 25A) and ride up to Bean & Bagel Cafe for refreshments.
We parked by Carmel Ave. It's a workout for the first few miles featuring hills like the Tatamy trail in Easton, PA where that crosses route 22. We were looking for a nice trail to just take it easy.
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