Find the top rated bike trails in Woodbury, 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.
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 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 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...
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 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,...
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...
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 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...
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....
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 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 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...
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...
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...
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...
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 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....
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....
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,...
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...
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 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,...
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 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...
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...
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...
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 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 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 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 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 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...
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...
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...
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...
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,...
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 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...
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...
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 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...
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...
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 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 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...
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 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 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...
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...
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...
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 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 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...
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...
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!
The trail itself is beautiful, however you take your life in your hands trying to pull in/out of Rt. 299 with your vehicle as the cyclists fly past the giant stop signs. There needs to be speed bumps or a gate to force them to stop. This is a fatality waiting to happen.
This entire trail has been paved for years.
We just finished riding this trail yesterday 9/9/19 and we have to say this is the best maintained paved trail we have ever rode our bikes on.
We started from the southern endpoint in Hopewell Junction and rode the trail to Poughkeepsie where we rode over the Walkway Over The Hudson on onto the Hudson Valley Rail Trail to New Paltz. There are train stations along the way where you can sit a a picnic table and eat or you can try one of the food trucks at the walkway before or after crossing the Hudson.
The trail is wide with plenty of room for three bikes to pass each other and there are not too many road crossings and none of them are busy roads. The thing that stood out to us as we rode was the trail signs directing you to the different points and the entrance and exit ramps to the many parking areas and local road access points along the way with the many benches to sit if you want to take a break. The trail is mostly wooded and there is not much to see as far as scenery but if you looking for a level smooth place to ride, this trail is a great choice.
This trail is just 1.2 miles from our home and is by far our favorite trail to ride. We enter the trail at the northern endpoint in Dutchtown in Haverstraw and ride to Nyack Beach Park and back. The 12.3 mile ride can be done in less then an hour or you can ride up the mountain and include the loop around Rockland Lake State Park where you can also park and enter the trail from. This trail winds up and down along Hook Mountain State Park with views from high over the Hudson River and then down along the rivers edge to Nyack Beach State Park. If you can get out during the week you can have the trail to yourself. Hybrid or mountain bikes are the better choice but you can make the trip on a road bike if your carful. If you live in this area you shouldn't miss this hidden gem.
We have biked this trail numerous times over the past 7 years and it's one of the trails we always go back to. We usually start at the Millwood parking lot and head north. The bridge over the Croton Reservoir is the highlight of the trip. There are horse farms and wooded sections along a rock gorge before you merge onto the Putnam Trailway. The trail is crowded on weekends so if you can get away during the week you will have this trail to yourself pretty much until the afternoon.
We had a wonderful time riding from Gardiner on the southern endpoint to Rosendale when we turned around due to the weather changing for the worse. We rode back to New Paltz and ate at "The Station" restaurant right on the trail before heading back to our car in Gardiner. The trail was level and wooded which was a blessing since the temperature was nearing 90 degrees. There are several bridges and streams to cross and beautiful scenery.
The only drawback was since its a packed dirt trail there was quite a bit of mud to evade or in some places unable to evade. The thick black mud coated our bikes and ourselves pretty good. Our advice is to avoid riding in the rain or just after a heaving rain and pick a nice dry day to ride.
Overall we loved the trail and will go back this fall and finish the northern section and adjacent trails.
I visited the walkway to roller skate, because I’d heard great things about it, and that it was super smooth. The rail trail on the Poughkeepsie side was super smooth and great, but the actual Walkway had huge cracks, some quite raised, every two feet. This made it impossible to flow and we basically had to march our skates across it, and I took two pretty bad falls (thank you, protective gear.) Soooo that was a real bummer. The rail trail on the other side was smooth for a bit but then got very rough. It was definitely worth the trip, but I wouldn’t recommend skating the walkway if you want a thoroughly enjoyable experience.
September 5 2019. Best Rail to trail we have ridden on. We started at the parking area in Hamden and went north 12 miles. Most of the trail was smooth as fresh tar. We almost did not do this trail because of the reviews but they were wrong. If you like smooth riding and well marked, this is the trail for you
There is trail maintenance work on going from Smith Street to the easterly East Hampton town line. Watch for equipment in use. This work was greatly needed.
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