Explore the best rated trails in Woodbridge, 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 55 trails covering 448 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.
This shared-use path was built as part of the improvement of NY State Route 347 in Suffolk County. SR 347 is a 15-mile arterial between Hauppauge and Port Jefferson, and the trail is envisioned to...
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 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 Bronx River travels from the mouth of the East River north to the Kensico Dam, providing views of the natural history of the area. Because the trail is under development, there are several gaps...
The old New York Central rail line that ran from the Bronx to northern bedroom communities in Westchester and Putnam Counties carried commuters during the workweek, but on the weekends tourists...
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 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 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...
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 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,...
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 Jones Point Path occupies an abandoned motor vehicle route (old US Route 9W). The path provides bicyclists with a relatively safe bypass to a dangerous section of busy US Route 9W near Bear...
The nicely paved Bethpage Bikeway runs alongside suburban roads for long segments of the route, but it’s much more than a suburban trail. Each on-road suburban stretch is broken up by one of three...
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 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 South County Trailway rolls 14.4 miles through one of the most densely populated parts of New York, but its route through pocket woodlots, parks, and golf courses and along riverbanks makes it...
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 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....
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 former “Old Put” commuter rail corridor that ran from the Bronx to northern bedroom communities in Westchester and Putnam Counties is popular once again, only this time it’s for people riding...
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...
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 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...
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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 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...
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...
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...
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...
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....
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 nicely paved Bethpage Bikeway runs alongside suburban roads for long segments of the route, but it’s much more than a suburban trail. Each on-road suburban stretch is broken up by one of three...
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 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,...
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...
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...
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...
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 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...
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 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...
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...
At first glance, there’s no evidence that an aqueduct ever existed along the Old Croton Aqueduct Trail. The trail is often a singletrack dirt pathway that winds through communities and trees and...
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...
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...
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...
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,...
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...
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...
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 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...
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 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...
While not a "rail-trail," the Hook Mountain/Nyack Beach Bikeway is a very scenic trail along the Hudson River in Rockland County. The southern half of this trail is flat and runs right along the...
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 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 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 nicely paved Bethpage Bikeway runs alongside suburban roads for long segments of the route, but it’s much more than a suburban trail. Each on-road suburban stretch is broken up by one of three...
Phase 1- the makings of a wonderful trail! Anxiously waiting for the completion of phase 2.
Great walk. But the section north of Woodhaven station is a dead end. I had to go back and walk city streets for a long section. All in all great walk from Soundview ferry station in the Bronx to Bronxville train station. I will return fir the next section
The Air Line State Park Trail is one of my favorite bike trails in Connecticut. Rode our bikes there last week and was very disappointed with the recently resurfaced section from the Cranberry Bog in East Hampton. The gravel that was used in the resurfacing is to soft and to deep. Has only been open for a week (10/28/2020) and it is already marred by craters from horses and foot traffic. The ride is bumpy like a wash board. At one point I swerved to miss a pile of horse droppings and got to close to the edge which then collapsed under my bike causing me to fall. What was once a favorite section of the trail for us, is now a major disappointment.
We parked by the pet store mentioned in a previous review and biked to just passed the covered bridge, maybe 6 miles out? Beginning of trail is rough but that ends quickly . Nice ride in the woods. Not much to see. It was a slight incline on the way out which made the return better. I wish there some benches along the way to take a break.
this is newly opened (was still closed when i checked in august at least) and paved and it is magical :) biked it today
This trail is an easy ride for everyone. It’s well maintained with plenty of benches to rest and a mixture of sun and shady spots. The end of this trail leads right into the Walkway over the Hudson.
I did the southern part of the trail from Massapequa park to Bethpage park. While the scenery and lakes are nice, the trail needs repair. There are many cracks and bumps especially near the beginning of trail. Also there are several road crossings but cars were careful to yield to cyclists.
One of the best trails I have done. Nice and smooth. You must do Walkway over The Hudson.
A nice 23 mile up and back from soundview. The most scenic part being from bronxville north to the dam. Definitely have a map handy though, as you will need to do street riding a few times. There are some hilly portions that will get you into gear changing which is nice. Bronxville has a great downtown with food options if you need to stop for a break. If this trail is ever connected it would be 5 stars for me. Solid ride and the dam at the conclusion is quite impressive.
My friend and I rode from Millwood on the North County Trail and just kept going. We ended up on the Putnam Trailway for a total of 46 miles. There are several decent hills on this segment of the trail. There are some street crossings but they are not very busy roads. You eventually come to the end of the trail, which is clearly marked. Near the end of the trail is a large reservoir. The trail is completely paved with just a few bumpy spots. We rode on 10/10 and the foliage has not changed much yet.
Level easy trail quiet and very pretty. Tricky entrance and exit onto busy road. Short easy trail. Wear boots muddy areas.
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