Find the top rated bike trails in Southbury, 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.
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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 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 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...
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 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 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...
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...
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 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 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 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 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...
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...
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,...
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,...
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...
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...
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 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...
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...
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...
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...
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 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...
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 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....
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,...
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,...
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 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 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 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 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...
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 nicely paved Bethpage Bikeway runs alongside suburban roads for long segments of the route, but it’s much more than a suburban trail. Each on-road suburban stretch is broken up by one of three...
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 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...
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,...
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...
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 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 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 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 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 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 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...
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...
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 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...
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 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 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...
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...
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...
Completely paved and in great condition from Wassaic to Millerton. Tree covered and shaded most of the way. Passing farmland, ponds, horses, sheep, apple farms. Only a few roads you pass over. One main road (not very busy at all) and a few smaller country roads (saw no cars). They are currently extending it farther North of Millerton but for now, the ride firm Waasaic to Millerton and back I believe is just about 20 miles.
Clean paved trail behind the high school. Great for biking.
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!
Having not ridden this trail before we made the mistake of trying to start at the very bottom end of the trail (0.0 mi), and later in the day than normal. Even though the TrailLink map indicates that parking was 2.5mi further north, we figured we'd give it shot. Mistake. Don't do that. There truly isn't any place to park, unless you want to leave your car randomly on the side of the rode on somebody's private property. 😂
We parked up in the Gardiner lot (Main & 2nd, 2.5mi mark on the trail). We rode north from there. What a great ride. Trail is mostly shaded, covered by the tress. The leaves where changing colors. It made for a very tranquil, fall covered tunnel feeling. The was flat and well maintained. We encountered other riders, joggers, and walkers along the way. We passed through farmland, apple orchards, and small communities. The trail takes you over roads and streams.
We stopped in New Paltz for lunch. We found a bike rack near the edge of the trail and locked our bikes there. We sat outside and enjoyed a nice meal at The Parish (New Orleans fare).
We continued our ride north for another 3mi or so before we had to turn back as it was getting late and didn't want to be on the trail when the sun set. (Note - we got a very late start at the beginning of the day). The trail north of New Paltz seemed to grow less traveled, a bit more narrow. As much as we enjoyed the souther portion of our ride, it seemed to me that the norther portion was shaping up to be even prettier.
We definitely plan to ride this trail again. (I've tagged it in my Google Maps) We will plan for a longer day so that we can explore further north of New Paltz. I think I will pack lunch in a backpack so that we can stop somewhere along the trail, stream side as there where some nice pull off areas.
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.
It’s mostly flat and has lots of great scenery, especially towards the south of the tail. I biked with my friend for 7 miles before we realized it would take another 7 to get back to the car. We loved it anyway! Great workout without feeling you worked out!
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.
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