Explore the best rated trails in Orange, 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 62 trails covering 504 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.
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 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...
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 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 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...
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...
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...
Bloomfield Greenway Multi-Use Trail is 1.8 miles between Bloomfield and Simsbury. The trail is envisioned to someday act as a connector between the City of Hartford and the Farmington Canal Heritage...
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...
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 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 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...
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...
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 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 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....
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 Mosholu-Pelham Greenway connects several parks and recreational opportunities in New York City's north and central Bronx neighborhoods. A portion of the trail is also part of the growing East...
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 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 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 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...
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...
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 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 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 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...
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...
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 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...
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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 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...
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 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 Kennedy Trail begins at the northwest corner of the 68-acre campus of John F. Kennedy Catholic High School in Somers. The town, which sits 30 miles from White Plains and 55 miles from New York...
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 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...
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 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 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 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...
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...
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 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...
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 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 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 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...
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...
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....
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 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 Raymond G. Esposito Memorial Trail travels from one end of the village of South Nyack to the other in 1 mile but greatly expands its reach by connecting with the Old Erie Path and a new shared-use...
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 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 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...
After many years of driving over an hour from NJ to Turner st in Hopewell Junction to ride the Dutchess trail to Walkway Over the Hudson - it was fun to go south / east in the other direction. I rode about 14.5 miles from Hopewell Junction to Holmes, a mile or so past Whaley Lake. That's roughy half of the Maybrook trailway . 29 miles round trip on a perfect day (7/22/21). As someone noted it is uphill 13 of these 14 miles. But hardly noticeable. Since the locomotives can't manage hills, the railroad builders levelled the right of way. Here with the existing track next to you - you're assured of no steep hills whatsoever. About 65 minutes to the turn around point, very leisurely done but flew back to Hopewell Junction at 17 mph and 40 minutes.
Will explore the other half next week starting in Brewster. I expect it to be just as enjoyable as this was.
I rode this trail out and back on 7/15/2021. Total out and back ride clocked in at 9.55 miles, 150 feet elevation change down heading North, so 150 feet uphill heading back South. I parked in the shopping plaza by the Taco Bell and rode the bike lane to the CTfastrack station where the trail starts.
For the most part the trail was clean except for a broken bottle just outside the first station, and a couple of trash cans that were left out for pickup on one of the sidewalk sections. There were not many people on the actual trail and every single one of them said hello and or thanked me for signaling when passing. The trail parallels not only the bus lane, but also an active train line, Amtrak is doing work on the line so in some places you can smell the new ties that they are installing. On the north end of the trail I stopped at a Dunkin' that was across the street from the station, and at the south end I stopped by the bike shop that is next to the hotel and part of the parking garage. There is a mix of businesses along the trail including convince stores and places to get food. The scenery is a mix of urban, industrial, tree lined, train tracks, and bus depots, if you pay attention you will even see a fiberglass Cobra Shelby along the sidewalk section. You will see plenty of busses, and if you are lucky maybe a train.
Recently repaved in sections, but done sloppily and left bumpy. The northern half of the trail has a lot of sunken and washboard sections that make it unpleasant to ride. From Van Cortlandt Park and about half way up the trail is nice, but from mid-point to where it connects to the north county trail is a mess.
As described, this trail varies from a wide gravel path to a single track dirt track with grass. We started in Tarrytown and went south. This is not a trail for a road bike but you are ok on a gravel bike as long as you are comfortable with rough spots and roots. The trail has lots of road crossings and they vary from neighborhoods where the cars have stop signs to steep hills where no one stops. Almost all have large granite curbs that you have to dismount to lift your bike over. As long as you are cautious you are ok. We made it to Yonkers when we turned around due to a raccoon which was blocking the trail and threatening to attack. Others on the trail kept going and one group was going all the way to NYC. We rode a bit of the River Walk as well which looks like it connects the southern part of this trail with the northern.
There is a bathroom at the Keepers House along with a museum and lovely docents who had lots of fascinating information about the aqueduct.
This was a fun outing to try something new but will likely not be on our list of gravel trails we love to ride and go to frequently.
This is a great ride for me to test my novice skills. I find myself coming back to here twice a week after work just to get a quick workout in
5 miles of hilly terrain along the river from Nyack to Haverstraw that consists of mostly stone dust with some asphalt. A couple climbs and descents are steep but not a problem for more experienced riders. If you are going to attempt with a road bike go with a bigger tire. The 28mm Armadillos worked well for me. Watch out for pedestrians, especially on the downhill sections.
This is a great trail for biking. Lots of hills so bring your ‘A’ game. You can also rent a bike from Pedego a tenth of mile away from the trailhead. The evoked will get you Thru the hills no problem. Pedego Stony Brook in East Setauket 690 NY 25A.
Okay, I road the whole trail, but on 2 days separated by a month. First I started at the Hopewell Junction parking lot (the end of the William R. Steinhaus Dutchess County Rail Trail). The second time I started riding in Brewster, near the end of the Putnam Valley trail. Either way you are going up a 1-3% grade until the level area near Whaley Lake.
Since it was paved with asphalt last year, this is a very smooth trail. There are several lovely watery areas on this trail and it is a great place for bird watchers. Except for either end, it is a somewhat secluded trail and very quiet. Thank you NYS for your investment.
This is all part of a section of NY's Empire State trail, and includes off road portions in Kingston, NY (the Wallkill Valley Rail Trail - gravel), continues through New Paltz, NY to the Hudson Valley RT, across the Walkway Over The Hudson and then to the Dutchess section. Then it continues through the Maybrook, Putnam, North County and South County rail trails to NYC. So you could ride more than 100 miles paved off-road.
Starting from either end Whaley Lake is the mid-point. From Hopewell Junction you ride east, north, and then south. Views include the Green Haven Correctional facility in Stormville, with its imposing and very high walls, and inmate sounds from inside those walls. From Brewster you ride northward past Ice Pond with its very long straight stretch (one mile?) for time trials. Going this way to the lake is shorter by about 3 or 4 miles than from Hopewell Jct. As you go upward the trail becomes very beautiful with flora and fauna. There are forest areas, beautiful mountain streams, marshlands, swamps, and then Whaley Lake. Also, there are many signs to "Stay on the Trail" to avoid snakes, poison ivy, and ticks, as well as "Stay off the Tracks" or private property.
Great day on the Maybrook. Rode from Lake Tonetta to Hopewell Junction and back, about 44 miles. Having previously ridden from Lake Tonetta to Whaley Lake, I was familiar with the basic trail..gradual uphill from Lake Tonetta to Whaley Lake, gradual downhill then from Whaley Lake to Hopewell Junction. The incline is very gradual, so not super hard but makes for a fairly long pull either way, so keep this in mind. Trail in fine shape. The first part to Whaley Lake passes several nice ponds with some hills in the background. And then Whaley Lake is beautiful, there’s a long stretch right alongside it. From Whaley Lake to Hopewell Junction, the trail is more secluded, passes over a couple of country roads and through rock cuts, and there are a few nice peeks through the trees and a view of the valley. Trail also passes the somewhat harrowing sight of Greenhaven prison briefly and also an area for NYPD canine training with big fences. But I could see this being pretty spectacular in the Fall, and it’s very quiet and peaceful. Hopewell Junction has a great stop at their old train station with picnic tables and restrooms…they did a great job with that. In Hopewell Junction you connect directly to the Dutchess County trail that leads to the walkway over the Hudson. All in all, a really nice trail, good variety of sections and sights. Note that you don’t pass through local downtowns per se, I saw restrooms at the Stormville parking area and at Lake Tonetta and Hopewell Junction. I understand there are a couple of services not far from some of the crossings (e.g. Route 292) but I did not go off the trail on this trip. Definitely worth a visit!
Easy access and very flat and straight. Nice trail to cycle for couples and families.
The trail great the only problem that is happing is that you need to repaint handicap parking areas.
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