Explore the best rated trails in Trumbull, CT. Whether you're looking for an easy walking trail or a bike trail like the Walkway Over The Hudson and Windsor River Trail . With more than 76 trails covering 567 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 Harlem River Greenway runs north-south along the Harlem River on the East Side of Upper Manhattan. The northern terminus is Dyckman Street and Harlem River Drive. Going west on Dyckman allows...
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...
Tallman Mountain State Park Bike Path is partially paved and bisects the Tallman Mountain State Park. The route provides a motor-vehicle-free way for bicyclists using US Route 9W to connect with...
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 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...
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 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 Kennedy Trail begins at Brick Hill Road and ends at the northwest corner of the 68-acre campus of John F. Kennedy Catholic High School in Somers. The cinder trail, built on a former rail bed,...
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Built on the former Erie Railroad main line, the 15-mile Heritage Trail runs through the small Orange County towns of Goshen, Chester, Monroe, and Harriman. The shaded trail runs through different...
You might expect a 4-mile rail-trail that passes through three downtowns to be excessively urban, but the quaint town centers on the Joseph B. Clarke Rail Trail are compact and surrounded by...
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...
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...
Closure Notice: As of 2021, the city is undertaking a series of construction projects in East River Park, which will result in ongoing closures to sections of the southern segment of the greenway...
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...
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...
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 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,...
Note: As of December 2021, the trail is fully complete except for a bridge on its southern end in Brewster; stairways on either side of the bridge are available for the detour. Construction on 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...
The Hudson River Waterfront Walkway is a 1.5 mile walkway along the bank of the Hudson River in Jersey City. The walkway offers stunning views of Manhattan as well as access to a number of ferries and...
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...
<p>This trail is the legacy of the first elevated roadway in the United States, constructed by William K. Vanderbilt in 1904. Vanderbilt created the parkway to get to his family’s estate in Long...
The Walkway Over the Hudson State Historic Park—the longest pedestrian bridge in the world at 1.28 miles—emerges from the trees and over the rooftops of the old riverfront town of Poughkeepsie,...
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 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...
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,...
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 Quinnipiac River Gorge Trail is a 1.3-mile rail-trail in Meridan, Connecticut. The trail occupies the former railbed of the Meriden, Waterbury & Connecticut River Railroad, a 17-mile line which...
Like Wantagh State Parkway, Ocean Parkway was built in the postwar 1930s to provide access to the crown jewel of the state park system, Jones Beach State Park. Unlike the former road, however, this...
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 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...
Randall's Island Park Trails offer a series of interconnected paved loops on an island in the New York City borough of Manhattan. The park offers a quiet setting, especially enjoyed by runners, with...
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 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...
Splayed over 1,146 acres in northwest Bronx, Van Cortlandt Park has a lot going on. The park is New York City's fourth largest and is home to the oldest municipal golf course in America. There are...
A former right-of-way of the NY & NJ Railroad. Near historical Mount Ivy which was the center of a Quaker settlement in the 18th century. Hiking along railroad bed and wildlife observation and...
The Hudson River Greenway (HRG) is one of the most popular places to ride, walk, and jog in New York City. It makes up part of the Manhattan Waterfront Greenway loop, the cross-state Empire State...
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 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 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 Mohansic Trailway is a rail-trail providing an important link between the North County Trailway and the Franklin Delano Roosevelt State Park. The trailway occupies a short-lived spur of the New...
The Cross Island Parkway Trail closely follows its namesake thoroughfare through northeastern Queens. From its northern end, you will soon enter Little Bay Park, which offers lovely views of 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 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 John Kieran Nature Trail is a short loop that borders Van Cortlandt Lake and its associated wetlands. It is a wonderful site for bird-watching. The trail also passes several sites of significance...
The Hudson River Greenway (HRG) is one of the most popular places to ride, walk, and jog in New York City. It makes up part of the Manhattan Waterfront Greenway loop, the cross-state Empire State...
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 Harlem River Greenway runs north-south along the Harlem River on the East Side of Upper Manhattan. The northern terminus is Dyckman Street and Harlem River Drive. Going west on Dyckman allows...
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...
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 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...
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 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 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...
<p>This trail is the legacy of the first elevated roadway in the United States, constructed by William K. Vanderbilt in 1904. Vanderbilt created the parkway to get to his family’s estate in Long...
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 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...
Built on the former Erie Railroad main line, the 15-mile Heritage Trail runs through the small Orange County towns of Goshen, Chester, Monroe, and Harriman. The shaded trail runs through different...
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...
You might expect a 4-mile rail-trail that passes through three downtowns to be excessively urban, but the quaint town centers on the Joseph B. Clarke Rail Trail are compact and surrounded by...
I drove the 70 miles from my home in Manhattan, not an easy drive both northbound and return given traffic. A friend suggested a parking place just South of Wassaic Station that is free all the time. Location is 14 Main Street, Wassaic, NY. I rode the 23 miles North to the point that the trail turns East along a public road. I turned around not because of riding on a public road, after all I ride in Manhattan, but because I would already have 50 miles before I got home. The trail is paved and mostly smooth. The multiple bridges are concrete slabs and a few are wooden. All have distinctive railings made of wood joined by steel cables. They compliment the natural trail very well. It is the CLEANEST trail that I’ve ever cycled, I saw only ONE discarded plastic bottle and it was down a ravine. Negatives: Pack an extra water bottle, I had two and rationed it carefully. I found NO place to buy a drink or snack. Take extra trail mix! There is only one intersection with heavy traffic. On the ones with very light traffic I found that the vehicles would stop and let you pass. Caution, just because the westbound car stopped that’s no guarantee that the eastbound vehicle will be as considerate. Few porta-potties; the ladies may not be pleased.
This trail is a good idea in terms of riding from Van Cartland Park to City Island. The execution however leaves a lot of room for improvement. The mostly asphalt paths are in rough shape -cracked, tree trunk and root damage, in need of lane markings both to designate the trail and to help keep people in the proper lanes (a big issue considering the number of walkers using this trail). There are signs to help navigate this trail but they are busy and difficult to read for bikers and could be more prominent as it’s easy to miss turns at intersections.
I ride a lot of rails trails and this frankly did not blow me away. There are some great sections with great canopy and nature but there's miles that feels like a glorified sidewalk next to traffic. A couple very large cracks and sections with bad pavement in the New Haven area. You'd think that would be the most maintained section but I guess not.
The Maybrook has quickly become one of our favorite rail trails. Basically brand new, uncrowded, lots of interesting sights along the way including multiple water views and lots of greenery.
Today we rode from the Brewster trailhead at Lake Tonetta both ways: Out and back to the CT line, and then out and back in the other direction up past the Ice Pond, for a total of about 20 miles. The first segment to the CT line was new to us; there is an on-road detour due to a bridge out at Peaceable Hill Road. You walk down a flight of steps, ride down Peaceable Hill Road to Rt. 6, turn left on Rt. 6, go down the hill, turn left again on Rt 6 and then ride up the hill past the Honda dealership where another set of stairs on the left will bring you back to the trail. These stairs are fairly steep but it can be done. The road has a shoulder but is a bit busy; experienced road riders will find this easy to navigate, others can simple walk along the sidewalk. Your reward is that the other end of the trail as you ride east is a very nice section past East Branch Reservoir, including a long section right along the water. One way mileage is about 5 miles, as the trail ends at the Connecticut line. The second section we rode, going North from the Brewster trailhead at Lake Tonetta, offers views of the “ice pond” and the “great swamp,” with hills in the distance. Today’s one way mileage for that section was also about 5 miles; a great ride, and you can ride much farther (we often go as far as Whalley Lake, just not today) as the trail goes all the way to Hopewell Junction where you can pick up the Dutchess Rail Trail. Check the Empire State Trail website for more info.
Rode the full trail on Memorial Day and really enjoyed it. It is well maintained; smooth pavement all the way. Mostly good shade and scenic, with lots of woods. A few spots along busy roads, but the trail is well protected throughout; always a sturdy railing between you and the cars. Goes through a few towns for snacks or lunch. Others warned about it being uphill heading north but I found it mostly flat. Some uphill as you approach the Putnam border, but mostly a gentle grade. Never came out of the seat. Overall a great trail.
Rode the full trail on Memorial Day and really enjoyed it. It is well maintained; smooth pavement all the way. Mostly good shade and scenic, with lots of woods. A few spots along busy roads, but the trail is well protected throughout; always a sturdy railing between you and the cars. Goes through a few towns for snacks or lunch. Others warned about it being uphill heading north but I found it mostly flat. Some uphill as you approach the Putnam border, but mostly a gentle grade. Never came out of the seat. Overall a great trail.
I prefer to travel out to Jones in the Fall and Winter months but this trail is great all year round. The board walk gets very crowded on the weekends and throughout the summer, however, the trail continues PAST the board walk (this trail map should be updated!) the concrete trail extends to the west end, there are paths that allow you to check out the fishing spots which require parking permits so being able to get there by bike for free is a plus. Just be aware that after memorial day you must pay $$$ for parking at Jones Beach, which is why I recommend this trail for the off season.
I never have been in this place before Is so nice, clean and secure. I would walk again definitely.
I began in Massapequa with the intention of finishing at Woodbury Road. I made it to Trail View Park at mile marker 8 and turned around. Picture perfect biking weather , but first ride of the season. I’ll definitely finish the trail next outing. The trail is well maintained, filled with walkers, joggers and bikers. I’d definitely recommend for walking and biking
My friend and I started at Hopewell Junction and glad we did. It was a nice leisurely ride up to Walkway on the Hudson in Poughkeepsie. The trail is very well maintained, and an easy ride. We locked the bikes up by the walkway, headed into town for an incredible lunch. I only wish it were more scenic but very happy we chose this way to ride.
I have been riding parts of this trail for about 24 years. It now goes from Harriman to downtown Middletown. To find the new section from Goshen to Middletown you have to go up West Main street in Goshen just past Clowes Ave on left then make a right where there are no trespassing signs and you will see the trail on your left. The big issue with this entire trail is about 60% of the people using it do not know or follow the rules. If one simple rule was followed, 100% of the issues would be eliminated. Walk, ride jog and skate on the right side of the trail and allow people to pass you on the left. Simple as that. Do not ignore verbal warnings or bicycle bells. When you hear a warning move to the RIGHT! I constantly encounter people using the middle or left side of the trail and ignoring warnings to move right. Many people have no concept of the fact that every time they use the trail, faster moving traffic WILL come up behind them. I have people move left after a warning, I have people refuse to move at all and I have people that stop and glare at you for ringing a bell or announcing a verbal warning. Bells and warnings are for safety people!!! I encounter people who ride bikes in groups that block the entire trail and fail to move right after a warning. It amazes me how confused people are. One simple rule people. One simple rule! Move right and stay right!
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