Explore the best rated trails in Southbury, CT. Whether you're looking for an easy walking trail or a bike trail like the Walkway Over The Hudson and Windsor River Trail . With more than 68 trails covering 517 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.
_164090_st.jpg)
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...
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 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,...
_164090_sc.jpg)
Built on the former Erie Railroad main line, the 15-mile Heritage Trail runs through the small Orange County towns of Goshen, Chester, Monroe, and Harriman. The shaded trail runs through different...
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 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...
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 Quinnipiac River Gorge Trail is a 1.3-mile rail-trail in Meridan, Connecticut. The trail occupies the former railbed of the Meriden, Waterbury & Connecticut River Railroad, a 17-mile line which...
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 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 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...
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 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...
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...
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 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...
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...
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....
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 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...
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...
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 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...
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...
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 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 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 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...
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 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 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 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...
_139112_sc.jpg)
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 Quinnipiac River Gorge Trail is a 1.3-mile rail-trail in Meridan, Connecticut. The trail occupies the former railbed of the Meriden, Waterbury & Connecticut River Railroad, a 17-mile line which...
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...
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 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 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...
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...
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...
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 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...
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 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 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 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...
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 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...
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...
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 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 Quinnipiac River Gorge Trail is a 1.3-mile rail-trail in Meridan, Connecticut. The trail occupies the former railbed of the Meriden, Waterbury & Connecticut River Railroad, a 17-mile line which...
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...
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...
Built on the former Erie Railroad main line, the 15-mile Heritage Trail runs through the small Orange County towns of Goshen, Chester, Monroe, and Harriman. The shaded trail runs through different...
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 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 Branford Trolley Trail is essentially a long footbridge occupying an old bridge along the route of an abandoned trolley track. The bridge links nature trails on both sides of the water through 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...
My wife and I rode this trail on 5/30/20, riding about 28 miles in all in a circle that also featured the Farmington Canal Trail. There are a number of different sections to this ride you need to be aware of before you go. We started at the parking lot on Red Oak Road, near the start. The first part of the trail, heading Northwest, runs on a very pretty course alongside the Farmington River, with lots of water views. Very scenic. There are several small towns along the way...in particular, Collinsville has a nice little downtown with places to eat, and places to stop with picnic tables alongside the river. The route then proceeds back East, until you get to the intersection with Route 202/44/Albany Turnpike. There is then some riding along regular roads: Lawton, Notch, West Mountain. The roads are basically flat with good sight lines, not difficult if you're an experienced rider (I wouldn't take kids on this section). Off of West Mountain, you'll find an entrance (a little hard to spot, there was a temporary sign there) to a hard packed dirt/cinder trail that proceeds for a short distance. It ends, and then following the markings on the road, you'll again ride on-road (Town Forest Road) again for a short distance, at which point you'll pick up another dirt/cinder trail (Stratton Brook State Park Trail) which ends at Brushy Hill Road. Cross Route 309/Farms Village Road and on the other side of the street is a paved trail that takes you down to Simsbury, where you pick up the Farmington Canal Trail south that takes you back to the Red Oak parking lot. Be aware that there are some varied signs/directions as you ride through Avon that take you behind offices etc. in a confusing way...I guess they didn't have the room to just cut the trail straight through. But soon you'll be back on the conventional trail. But as for the ride:
What's nice about this ride was its diversity: the section along the river, some riding on country roads, the dirt/cinder path through the woods, and the more conventional trail from Simsbury south. Lots of places to stop and eat (especially Simsbury), many trail parking lots, we saw a lot of bathroom options . We know the Farmington Canal Trail well, were glad to discover this very nice connected option! Definitely check out the map at their website before you go. One more thing: we used our road bikes, and we were able to navigate the short dirt sections pretty easily...you don't need a mountain bike just for that.
For the most part the bike trail is very well paved with the exception of a small strip that was slightly bumpier. We parked at the parking lot on Executive Drive and Washington Avenue, it’s free. The path is not super-scenic but it’s a nice ride nonetheless.
Great trail, well-groomed. Lots of trees on each side of the trail so good shade. Everyone is respectful of their space and good bike etiquette. I brought my dogs and it was a perfect four mile walk.
Because this is close and I'd never been to it, I finally did and what I found was something that was a very old rail path that had never had any work done to be "bikeable". The Western Section is owned and managed by a Land Trust who has not even done the work to make it walkable. Trail is covered by fallen trees and clearly, zero tail maintenance is going on. At times the only passable place to walk and carry your bike are narrow trails that leave the "path" and then return where there is a dry spot. Worse trail I've even been on in my 70 plus years of biking. It's an embarrassment and should be listed in your book or on-line stuff.
Dennis Sears.
It was so much fun , I don’t know if I got lost or if it really gets difficult at some point but it was challenging haha
Took off from Silver Lane on the Charter Oak Trail to get started. 1/2 mile take a right to get on this trail. The surface is ok but showing a lot of grass in the frequent pavement cracks. Woody vegetation is leaning into the trail. The trail twists and turns. There are many places where the visibility is poor especially on faster down hill areas. Mowing back everything would help. Most problematic is the very poor signage. With all the changes in direction improved signage on this trail is a must.
Road this trail and found it in good condition. I had hybrid 1.95 tires on my bike. There are several road crossings that require careful attention. The trail was being well used which is great to see. I road it from the Hop River trail junction to its end in Rockville. 4.2 miles and a grade of mostly up made it a good test for a fast ride. Watch for fast cars at the crossings.
I road the entire nearly six mile trail today. The scenery was beautiful and the water views gorgeous, if you could look away from the trail surface. The asphalt is tired, cracked and roots cross it in many locations. I road a street bike with narrow tires which was a mistake. The trail surface is better suited to MT bike or larger tires.
I started at the southern end. Follow along the east side of the factory building to the newly refurbished parking lot with picnic tables. Then the trail goes north to the intersection with Route 190. Turn west to get to Route 159 and back track over the CT River to see the whole trail. At 14 MPH, I need to get my fillings replaced due to the rough surface. The CT Parks Division needs to put this trail on the rehab list. Despite my complaints, it's a pretty trail in need of work.
Wow! Once open, the Undermountain Road to Millerton gap is going to be spectacular. I note that the northernmost section going south from Undermountain Road to Boston Corners Road, about one mile long, is now open and beautiful. The next two miles going south, to White Horse Crossing Road, includes a gorgeous mile long raised section going through a beautiful wetland. Parts, including that section, are currently paved but construction is ongoing. Later this season this will be the place to ride!!
I rode this trail in 2018 and loved it, the memory of that day, even the car drive getting there, always bring a smile to my face. It is not for bikes with racing tires, but most others will do fine if the region has not had any rain recently. It is not a tough path, even with its few small hills. Beautiful scenery very close to the river, mostly shaded from the trees. The trail seemed to end near a highway bridge where I sat with my lunch right on the river.
With a drive of almost 2 hours, I would not have visited this area without the this trail. If and when the trail is expanded I will be back. Trails do bring tourists and money into new areas, so good job New Milford.
Passed through here with a friend on our way to Montreal in June of 2018. Easy to miss, but the gentleman who lives in the house at the southern end helpfully pointed it out.
If you can get through the initial brush, it clears up just fine. Besides being gnatty, it's like a secret garden, and about halfway through there was a sort of meadow filled with flowers.
No special bike here, just two tourers from the 1980s. I had 700x35 Schwalbe Mondials on, my friend had similarly sized but totally slick tires. He did alright, but said it could have been better with some tread. We were both fully loaded with panniers, etc.
I can't quite remember, but the fallen tree mentioned above was actually quite light, more like a large branch. So I moved it out of the way!
According to data I found about the trails being put together for the Empire State Greenway, it's 1.9 miles long. Definitely preferable to climbing and descending 9W with the cars, which we had done a few weeks before in preparation for the full tour. Bleh. I'd rather risk having to backtrack and THEN take the highway if the trail were impassible.
Traillink is a free service provided by Rails-to-Trails conservancy
(a non-profit) and we need your support!
TrailLink is a free service provided by Rails-to-Trails Conservancy (a non-profit) and we need your support!
Map Search
_139112_st.jpg)
