Find the top rated trails in Woodbury, 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 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 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...
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...
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...
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 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 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 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...
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...
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 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 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 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 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....
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...
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 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 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...
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 South County Trailway is a zippy paved trail heading north from Yonkers through the Hudson River Valley communities of Hastings-on-Hudson, Dobbs Ferry, Ardsley, Irvington, Greenburgh, and...
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 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 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...
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 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...
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...
Shawangunk, Walden, and Wallkill Rail Trail is built on a railroad right-of-way that was abandoned by Conrail in the late 1970s. Conrail and its predecessors, Penn Central, New York Central, and The...
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 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 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...
These three contiguous trailsthe Raymond G. Esposito Memorial Trail, Old Erie Path and Joseph B. Clark Trailoccupy the former right-of-way of the Erie Railroad's Nyack and Piermont Branch. Each...
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...
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 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 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...
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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 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 Jack Harrington White Plains Greenway was recently renamed to honor a long-time member of the city's conservation board. The trail's corridor follows the former New York, Westchester & Boston...
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 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...
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 Jack Harrington White Plains Greenway was recently renamed to honor a long-time member of the city's conservation board. The trail's corridor follows the former New York, Westchester & Boston...
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...
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...
These three contiguous trailsthe Raymond G. Esposito Memorial Trail, Old Erie Path and Joseph B. Clark Trailoccupy the former right-of-way of the Erie Railroad's Nyack and Piermont Branch. Each...
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...
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...
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...
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 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 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 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"...
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 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....
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 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 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...
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 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...
August 2017
It was a great ride, next to a river, shady, smooth, and there is a parallel Farmington Canal trail that meets this one at the southern end. The north end is near a conjesting roadway and was supposed to continue on a non-paved section, but I could not find it. Go check it out.
Dateline June 21, 2018, 4:00 pm, sunny 81F.
I wish there were more time that day to continue longer, onto the connecting trails. After driving 2.5 hours to another trail only to find the parking lot closed I had little time to enjoy this one, but it is nice.
ADVICE: If you are driving farther than 30 minutes (like I often do for Trailink trails), (1) always review the trail listing on this site for updated information, (2) bring more than one parking lot address, (3) and a second choice trail with 2 parking lot addresses. And/or get the mobile app.
Totally ignore the previous comment about the trail being rough w/ large rocks. We just rode from Gardiner to Rosendale. Trail is great. My wife a sissy on rough stuff and even she thought the trail was easy. She was on a Hybred...did fine. That previous lady must walk over sidewalk cracks! I’m just glad we ignored her comment! I’d have been pissed if the wife had stayed home. (So would she)! We stopped in New Paltz and had lunch at Los Jalapeno’s! Best Guacamole Dip we’ve ever had!! Burrito was excellent also! Highly recommend (and we’re from Texas) Overall..I highly recommend this trail for ANY level of cyclists!
The Portland section does not connect up to the East Hampton section and the rest of the Air Line Trail. I found out today when I thought I was going to ride from Portland to the Air Line Trail North. I only rode 2 miles and the trail abruptly ended.
The Air LIne Trail South is now open through part of Portland. Parking is off of Middle Haddam Rd. in Portland.
My husband and I recently explored this trail on our road bikes with a 2-year old in a bike trailer.
Pros:
1) Plenty of shade and tree cover. Perfect for those scorching summer days!
2) Most (not all) people know how to stay to one side of the road, but if you give a friendly "On your left!" or "On your right!" they'll quickly move over for you.
3) Easy entry. We parked at Briarcliff Manor Public Library and felt completely safe leaving our car there. The entrance to the trail is in the parking lot, next to the library (big red building). Plus, there is a public bathroom in the tented area, as well as plenty of picnic tables.
4) Trail is well marked.
5) Most (not all) cyclists are respectful and know how to conduct themselves on two wheels.
Now, the cons:
1) Considerable amount of bumps from tree roots, cracks, potholes, dips, and corroded asphalt, which honestly seems like the norm when it comes to bike trails. I think it's just impossible to have a completely smooth surface when nature is so unpredictable. My butt was a bit sore and my kid said "ouch" a few times, but we had no problems getting through it on our road bikes. In fact, you'll see plenty of cyclists training on road bikes with no problems whatsoever.
2) Getting to the North County Trail seems impossible, at least from the Public Library. We discovered it would require riding ON the shoulder of the Saw Mill River Parkway. No way!
3) Bathrooms do not exist, so make sure to pee before you head out.
Tip: From the Library, we rode about 12 miles to Rivertowns Square Shopping Plaza in Dobbs Ferry to grab lunch at Chipotle. It's a quick 5 minute detour from the trail and you'll need to cross Saw Mill River Parkway, but there are traffic lights and crosswalks in this section. We also stopped at Menchie's Fro Yo which is in the same shopping plaza. There's also a Starbucks and Chop't if you're in need of a salad and caffeine.
Enjoy your ride!
We have ridden this trail before, and really enjoyed it, especially the part near the ponds below Oxford Airport. We expected it to be somewhat rough, and we are always willing to walk through particularly wet/mucky areas and to put up with rough stretches. However, the trail has really gotten much worse. After about 2-2.5 miles in, it became extremely sandy/silty, and we could only ride on the narrow edges. Then at about 4 miles in, there was a stream flowing through the whole trail, with nothing but mud and muck; no way to ride through, as it continued as far as we could see, so we had to turn around. End of ride for the day...
I love walking this trail. I have yet to make it to the end with the kids as they get tired we have gone most of the way. I walk there a few times a week with them. They love seeing the turtles in the water. Only thing I dislike is those who dont clean up after their dogs. I have stepped in dog doo on the trail, and alot of those who do clean up throw the colored baggies in the bushes so you always see colored bags oi n the ground and un the tree.if your not going to take the bag with you then leave the pool it will eventually go away your bag on the other hand will go nowhere :(
Absolutely beautiful scenery. Asphalt path was in great condition. People on the trail were friendly. Maps were available in Millerton as well as a clean porta potty. Many sections were shaded to provide some relief from the heat! Millerton is a small, quaint village with plenty of nice shops to check out.
The OCA trail offers a rich variety of surfaces and surroundings. I rode a commuter bike with 38mm slicks and did just fine, even through the muddy sections. I picked the trail up in Yonkers off the South County with a bit of street riding. This initial section runs through some rough spots in Yonkers and includes some on-street sections. After reaching the northern neighborhoods of Yonkers, it all starts to feel European with back-to-back posh villages, mansions, and views of the Hudson. There are even some interesting stone ruins, not to mention the Lyndhurst Mansion grounds.
The trail comes and goes a bit further north and you'll find yourself on the road more than you may like, but there are some deeply wooded sections and a fun climb to a bridge over Phelps Way. There is an aqueduct museum along the way and many clear signs of former aqueduct works.
I highly recommend this trail and shall return to it many times.
Looks like the bridge over Rt 6 in Bolton is finally going in. Connection to the Hop River Trail this Summer?
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