Find the top rated trails in Southbury, 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.
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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 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 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...
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 Bronx River Greenway offers 23 miles of paved pathway in New York's Westchester and Bronx counties. The developing trail is open in disconnected segments largely paralleling the Bronx River...
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...
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...
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...
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...
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 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 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...
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 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 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...
These three contiguous trails—the Raymond G. Esposito Memorial Trail, Old Erie Path and Joseph B. Clarke Trail—occupy the former right-of-way of the Erie Railroad's Nyack and Piermont Branch. Each...
The Bethpage Bikeway is one of Long Island's most popular trails. It connects Merrick Road in Massapequa with Bethpage State Park, and includes additional trail north to Trail View State Park in...
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 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...
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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 Wallkill Valley Rail Trail extends 21 miles between Kingston and Gardiner along the route of the old Wallkill Valley Railroad, which, in the late 1800s, carried produce from Ulster County farms to...
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 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...
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 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...
These three contiguous trails—the Raymond G. Esposito Memorial Trail, Old Erie Path and Joseph B. Clarke Trail—occupy the former right-of-way of the Erie Railroad's Nyack and Piermont Branch. Each...
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Much of New York's 15-mile Heritage Trail, sails past wide fields of corn and wheat. The trail starts in Harriman at the Mary Harriman Park. From there, it heads northwest to Monroe. At Crane Park,...
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...
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...
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 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...
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...
These three contiguous trails—the Raymond G. Esposito Memorial Trail, Old Erie Path and Joseph B. Clark Trail—occupy the former right-of-way of the Erie Railroad's Nyack and Piermont Branch. Each...
The Bethpage Bikeway is one of Long Island's most popular trails. It connects Merrick Road in Massapequa with Bethpage State Park, and includes additional trail north to Trail View State Park in...
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 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 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...
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...
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...
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 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 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...
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 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 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...
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 Bronx River Greenway offers 23 miles of paved pathway in New York's Westchester and Bronx counties. The developing trail is open in disconnected segments largely paralleling the Bronx River...
These three contiguous trails—the Raymond G. Esposito Memorial Trail, Old Erie Path and Joseph B. Clark Trail—occupy the former right-of-way of the Erie Railroad's Nyack and Piermont Branch. Each...
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 Wallkill Valley Rail Trail extends 21 miles between Kingston and Gardiner along the route of the old Wallkill Valley Railroad, which, in the late 1800s, carried produce from Ulster County farms to...
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 Bethpage Bikeway is one of Long Island's most popular trails. It connects Merrick Road in Massapequa with Bethpage State Park, and includes additional trail north to Trail View State Park in...
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...
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 EPCAL Alternative Transportation Path loops around the 2,900-acre Enterprise Park at Calverton (hence its name: EPCAL) on New York’s Long Island and links to the Town of Riverhead’s 65-acre...
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 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...
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....
Just a mile or so due North is another EXCELLENT off-road biking destination: Wildwood State Park on Long Island Sound. 700 undeveloped acres of mountain biking and hiking trails open to the public.
https://parks.ny.gov/parks/68/details.aspx
Great ride, very easy, anyone can do it. It can be accomplished on a Road Bike. Surface was flat, smooth and clean.
Parked at western end of trail in a very new parking lot on Rt 299 across from the Lowe's. Trail is beautifully paved all the way to the Walkway Over the Hudson, some of the pavement appeared to put down only days before we rode on it. State of NY is doing a fantastic job making this and the Walkway a great destination ride, installing modern bathrooms/visitor center on each side of the Walkway (open already on the west side of the river and under construction on the eastern side). On eastern side, seamlessly connects to another 13 mile rail trail. You will have to ride very slow over the Walkway, as there are a lot of walkers, but you're going to want to stop and take pictures anyway!
We enjoyed the ride through the country side and found the trail fairly empty on a early October Wednesday morning. Several parts of the trail were muddy and narrow. The best stop was the Rosendale Trestle with spectacular view. Worth riding again.
We parked at Tony Williams Park rode past the Walkway over the Hudson down to mile marked 8 on the Duchess Trail where we stopped on a bench for lunch. The path is wide and mostly smooth and only one construction area (putting in a modern restroom on southside of the Walkway). We would rate this the best trail we have ever been on as far as access, parking, restrooms (including port-a-potties in some areas) and very few rode/driveways to cross. We rode on a Thursday morning early October and the path was not crowded. Our 20 mile round trip was Fantastic!
This is a beautiful paved trail for biking, running, walking, strollers, and wheelchairs. It is well-kept and offers scenic views--from rolling fields, to bridges, to train cars, to even an old cemetery. My husband and I biked the entire length and back on a gorgeous fall day. It was a really nice ride, but be aware that it is often a false flat trail. One other major thing to be aware of is that you CANNOT access this trail from Mary Harriman Park in Harriman. Your best bet is to access if from Monroe. If heading east on the trail toward Harriman, the trail comes to a dead end fenced off bridge with no access and you're forced to turn around and go back the way you came. Hopefully someday they will fix this and extend it into Harriman for better access. That is my only complaint about this otherwise beautiful trail.
I love to walk the trail and have since 1971, the cross over on Whitney Ave in Trumbull is Terrifying, The cars cannot see any one passing the road way until they are in the roadway. The line of sight is completely obscured by vegetation and the small sign in the middle of the Street??? I have seen people run right across the road with out even slowing down prior to or while crossing Whitney Ave. I personally saw a woman hit the side of a car as she could not stop running in time to avoid the car. This section is an accident waiting to happen. Whitney Ave. crossing needs to be safer for both motorist and trail user.
No meter parking along Kimball Ave before Palmer Rd.
To avoid getting lost trying to connect to the bike path after passing the Scarsdales Train Station: exit at the station go north on East Pkwy; Rt on Crane Rd; Lf on Fox Meadows Rd (after Fenimore Rd) it changes to Walworth Ave and Lf on Greenacres Ave. The 2nd entrance to the trail is about 1/5 mile on the right.
There are restrooms when you reach the Kensico Dam.
Paved path of just about 8.5 miles (all off the regular roadways) provides a great pathway for all skill levels. Beginners can take a leisurely ride with gradual inclines or more experienced riders can challenge themselves with speed and cadence. The path is completely free of roadway dangers as it is only open to walkers, bikers, skaters, etc. It has quite a bit of shady areas to stay out of direct sun due to its location near the woods. Some nice natural scenery. Start/end point located near Veteran Memorial and Isaac Dog Park for other points of interest.
In April 2018 the Windham Town Council approved $1,300,000 for rehabilitation on the Willimantic River bridge behind Mackeys. This would include 800 feet of trail. It was put out for bids due on July 26th. I haven't seen any work yet. There is still the bridge over the Hop River which looks to be in terrible shape and may never be repaired.
Quick update that a stretch of trail less than one mile between Cornwall Av. and West Main St. in Cheshire is now officially opened, avoiding a detour onto Willow St. There is now a continuous, paved, off-road stretch of trail some 25 miles from Temple St. in downtown New Haven to Lazy Lane in Southington.
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