Find the top rated bike trails in Litchfield, whether you're looking for an easy short bike trail or a long bike trail, you'll find what you're looking for. Click on a bike trail below to find trail descriptions, trail maps, photos, and reviews.
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...
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 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 Manhan Rail Trail, well integrated into the local communities it serves, offers a pleasant ride or stroll. It conveniently weaves together parks, community points of interest, neighborhoods, and...
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 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,...
Connecting the Walkill River and Shawangunk Ridge, the aptly named River-to-Ridge Trail, which opened in September 2018, runs from New Paltz to the Mohonk Preserve. Begin at the Carmine Liberta Bridge...
While the Wallkill Valley Railroad no longer carries fruits and vegetables from Ulster County to New York City, trail users can still discover small, family-owned farms and farmers markets serving up...
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 Massachusetts Central Railroad was destroyed by a hurricane in 1938, but the 104-mile corridor is being reborn as a cross-state rail-trail. Currently, nearly 40 miles from Boston to Northampton...
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 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 O&W Rail Trail provides a glimpse into the area’s history from the perspectives of both a historical canal and a railroad. The Delaware & Hudson (D&H) Canal carried coal from Honesdale,...
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...
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 William R. Steinhaus Dutchess Rail Trail—named for the county executive who championed it—is a local treasure in the Hudson Valley region of New York. The 13.1-mile trail runs through what seems...
The Kingston Point Rail Trail will be a paved pathway stretching from Kingston’s midtown to the Rondout Creek waterfront, connecting important points in the community such as Kingston High School,...
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 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...
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...
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 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...
While the Wallkill Valley Railroad no longer carries fruits and vegetables from Ulster County to New York City, trail users can still discover small, family-owned farms and farmers markets serving up...
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 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...
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 Walkway Over the Hudson State Historic Park—the longest pedestrian bridge in the world at just over 1.6 miles—emerges from the trees and over the rooftops of the old riverfront town of...
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 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 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 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...
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 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 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 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 William R. Steinhaus Dutchess Rail Trail—named for the county executive who championed it—is a local treasure in the Hudson Valley region of New York. The 13.1-mile trail runs through what seems...
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...
Offering a picturesque and family-friendly adventure, the Hudson Valley Rail Trail stretches 7.1 miles through hardwood forests, over Black Creek, and under two spectacular stone-arch bridges....
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...
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...
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 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 Massachusetts Central Railroad was destroyed by a hurricane in 1938, but the 104-mile corridor is being reborn as a cross-state rail-trail. Currently, nearly 40 miles from Boston to Northampton...
The Ashokan Rail Trail is an 11.5-mile multi-use trail that traces the northern edge of the Ashokan Reservoir, which provides a large proportion of New York City's drinking water. The trail sits on...
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...
The Manhan Rail Trail, well integrated into the local communities it serves, offers a pleasant ride or stroll. It conveniently weaves together parks, community points of interest, neighborhoods, and...
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...
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...
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...
Offering a picturesque and family-friendly adventure, the Hudson Valley Rail Trail stretches 7.1 miles through hardwood forests, over Black Creek, and under two spectacular stone-arch bridges....
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...
Connecting the Walkill River and Shawangunk Ridge, the aptly named River-to-Ridge Trail, which opened in September 2018, runs from New Paltz to the Mohonk Preserve. Begin at the Carmine Liberta Bridge...
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 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...
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 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 Walkway Over the Hudson State Historic Park—the longest pedestrian bridge in the world at just over 1.6 miles—emerges from the trees and over the rooftops of the old riverfront town of...
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 William R. Steinhaus Dutchess Rail Trail—named for the county executive who championed it—is a local treasure in the Hudson Valley region of New York. The 13.1-mile trail runs through what seems...
Great trail for biking and just walking. So nicely maintained!
I did the loop today going north on this River Trail then back south on the FCT. The gravel is at mile 12.3 after a little on the road segment but it only lasts about 3/4 mile. I had to go very slowly on the gravel dust because I was on my road bike (22mm) but it was tolerable because it was short (&pretty). At the entrance to the Stratton State Park a sign indicates you can take the road downhill to Simsbury felt safe. froDOWNdown to Simsbury which was much better on thin tires. indicating on esign The on the road section was well marked today - although many of the signs were large temporary ones. I how
This trail starts out OK, but as you move further North, into to country the trail narrows and is less maintained. My biggest concern is there is not enough parking places, entrances , and no benches.
This is an amazing trail" with windy. curves, up and down climbing, plenty of benches, and lots of awesome bridges.
Beautiful and no crowded from Amenia to Milerton - 8 plus miles from the parking lot indicated on the map. Trail ends in Millerton - I did not ride along rite 22 to pick up the rail trail again for the final five r so miles, as it is crazy town to ride on Route 22. Overall, a pleasant there and back (I went past the parking lot to make a twenty mile ride). I hope that the trail does get connected and soon.
I started in Hurleyville. Heading East, once the asphalt ended, I clearly had the wrong bike with me. It's a fat-tire trail. It was so bad that I pulled Google Maps to do a parallel side road just to see if it got any better further up. It didn't.
I went back through Hurleyville to the other end. It stops at Denman road. However, there is a gravel path that continues. Oops..after a couple of miles it just dead-ends in an industrial parking lot. I rode up to Liberty (that was pretty pointless since it was Monday and no place to eat was open). I took 52 back to Cross Farm and then down Denman back to the trail and back to Hurleyville.
I wouldn't recommend this stretch.
Completely paved and in great condition from Wassaic to Millerton. Tree covered and shaded most of the way. Passing farmland, ponds, horses, sheep, apple farms. Only a few roads you pass over. One main road (not very busy at all) and a few smaller country roads (saw no cars). They are currently extending it farther North of Millerton but for now, the ride firm Waasaic to Millerton and back I believe is just about 20 miles.
Clean paved trail behind the high school. Great for biking.
Beautiful in fall, but a workout going from Brewster. A few major hills.
Enjoyed a ride from Simsbury past the Mass line and back. As always, well maintained, a few frost heaves here and there but nothing major. As we were riding we noticed some trail widening in progress in Simsbury/Granby. The area across the Mass line is very well maintained and passes some fields and a nice golf course. Thoroughly enjoyable!
Having not ridden this trail before we made the mistake of trying to start at the very bottom end of the trail (0.0 mi), and later in the day than normal. Even though the TrailLink map indicates that parking was 2.5mi further north, we figured we'd give it shot. Mistake. Don't do that. There truly isn't any place to park, unless you want to leave your car randomly on the side of the rode on somebody's private property. 😂
We parked up in the Gardiner lot (Main & 2nd, 2.5mi mark on the trail). We rode north from there. What a great ride. Trail is mostly shaded, covered by the tress. The leaves where changing colors. It made for a very tranquil, fall covered tunnel feeling. The was flat and well maintained. We encountered other riders, joggers, and walkers along the way. We passed through farmland, apple orchards, and small communities. The trail takes you over roads and streams.
We stopped in New Paltz for lunch. We found a bike rack near the edge of the trail and locked our bikes there. We sat outside and enjoyed a nice meal at The Parish (New Orleans fare).
We continued our ride north for another 3mi or so before we had to turn back as it was getting late and didn't want to be on the trail when the sun set. (Note - we got a very late start at the beginning of the day). The trail north of New Paltz seemed to grow less traveled, a bit more narrow. As much as we enjoyed the souther portion of our ride, it seemed to me that the norther portion was shaping up to be even prettier.
We definitely plan to ride this trail again. (I've tagged it in my Google Maps) We will plan for a longer day so that we can explore further north of New Paltz. I think I will pack lunch in a backpack so that we can stop somewhere along the trail, stream side as there where some nice pull off areas.
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