Waterbury Mountain Biking Trails and Maps

867 Reviews

Looking for the best Mountain Biking trails around Waterbury?

Find the top rated mountain biking trails in Waterbury, whether you're looking for an easy short mountain biking trail or a long mountain biking trail, you'll find what you're looking for. Click on a mountain biking trail below to find trail descriptions, trail maps, photos, and reviews.

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Activities
Length
Surfaces
Type
11 Results
Activities
Length
Surfaces
Type

Air Line State Park Trail

54.6 mi
State: CT
Ballast, Dirt, Gravel

Billings Trail

3.3 mi
State: CT
Dirt

Branford Trolley Trail

0.6 mi
State: CT
Concrete, Crushed Stone, Gravel

Hop River State Park Trail

20 mi
State: CT
Crushed Stone

Kennedy Trail

1.7 mi
State: NY
Cinder

Larkin State Park Trail

10.8 mi
State: CT
Cinder, Crushed Stone, Dirt, Gravel

New Milford River Trail

5 mi
State: CT
Asphalt, Crushed Stone, Dirt

Old Croton Aqueduct Trail

22.8 mi
State: NY
Asphalt, Concrete, Dirt

Redstone Rail Trail

1.4 mi
State: MA
Asphalt

Stratton Brook State Park Trail

1.2 mi
State: CT
Asphalt, Cinder, Crushed Stone
Trail Image Trail Name States Length Surface Rating
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...
CT 54.6 mi Ballast, Dirt, Gravel
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...
CT 3.3 mi Dirt
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...
CT 0.6 mi Concrete, Crushed Stone, Gravel
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...
CT 20 mi Crushed Stone
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...
NY 1.7 mi Cinder
Canopied with deciduous trees for most of its 10.8 miles, the Larkin State Park Trail (a.k.a. Larkin Bridle Path) is primarily a wilderness trail, with wooded vistas, wetland views and sparse...
CT 10.8 mi Cinder, Crushed Stone, Dirt, Gravel
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....
CT 5 mi Asphalt, Crushed Stone, Dirt
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...
NY 22.8 mi Asphalt, Concrete, Dirt
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...
MA 1.4 mi Asphalt
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...
CT 1.2 mi Asphalt, Cinder, Crushed Stone
Thanks to skilled engineers with the former Hartford, Providence, & Fishkill Railroad, the pretty Vernon Rails-to-Trails overlooks ravines and streams and passes between rock walls verdant with ferns...
CT 4.2 mi Crushed Stone, Dirt

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Trails by activity

Old Croton Aqueduct Trail

NY - 22.8 miles

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...

Hop River State Park Trail

CT - 20 miles

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...

Stratton Brook State Park Trail

CT - 1.2 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...

Billings Trail

CT - 3.3 miles

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...

Accordion

Vernon Rails-to-Trails (Hop River State Park Rockville Spur)

CT - 4.2 miles

Thanks to skilled engineers with the former Hartford, Providence, & Fishkill Railroad, the pretty Vernon Rails-to-Trails overlooks ravines and streams and passes between rock walls verdant with ferns...

Redstone Rail Trail

MA - 1.4 miles

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...

New Milford River Trail

CT - 5 miles

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....

Vernon Rails-to-Trails (Hop River State Park Rockville Spur)

CT - 4.2 miles

Thanks to skilled engineers with the former Hartford, Providence, & Fishkill Railroad, the pretty Vernon Rails-to-Trails overlooks ravines and streams and passes between rock walls verdant with ferns...

Stratton Brook State Park Trail

CT - 1.2 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...

Hop River State Park Trail

CT - 20 miles

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...

Branford Trolley Trail

CT - 0.6 miles

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...

Accordion

Old Croton Aqueduct Trail

NY - 22.8 miles

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...

Air Line State Park Trail

CT - 54.6 miles

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...

Kennedy Trail

NY - 1.7 miles

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...

Redstone Rail Trail

MA - 1.4 miles

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...

New Milford River Trail

CT - 5 miles

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....

Billings Trail

CT - 3.3 miles

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...

Larkin State Park Trail

CT - 10.8 miles

Canopied with deciduous trees for most of its 10.8 miles, the Larkin State Park Trail (a.k.a. Larkin Bridle Path) is primarily a wilderness trail, with wooded vistas, wetland views and sparse...

Air Line State Park Trail

CT - 54.6 miles

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...

Billings Trail

CT - 3.3 miles

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...

Vernon Rails-to-Trails (Hop River State Park Rockville Spur)

CT - 4.2 miles

Thanks to skilled engineers with the former Hartford, Providence, & Fishkill Railroad, the pretty Vernon Rails-to-Trails overlooks ravines and streams and passes between rock walls verdant with ferns...

Stratton Brook State Park Trail

CT - 1.2 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...

Accordion

Redstone Rail Trail

MA - 1.4 miles

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...

Larkin State Park Trail

CT - 10.8 miles

Canopied with deciduous trees for most of its 10.8 miles, the Larkin State Park Trail (a.k.a. Larkin Bridle Path) is primarily a wilderness trail, with wooded vistas, wetland views and sparse...

Branford Trolley Trail

CT - 0.6 miles

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...

Kennedy Trail

NY - 1.7 miles

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...

New Milford River Trail

CT - 5 miles

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....

Hop River State Park Trail

CT - 20 miles

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...

Old Croton Aqueduct Trail

NY - 22.8 miles

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...

Recent Trail Reviews

Larkin State Park Trail

Disappointing; unrideable, even with hybrid bikes

May, 2018 by rsbkeys

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...

Sue Grossman Still River Greenway

Love walking

May, 2018 by casiluv1982

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 :(

Harlem Valley Rail Trail

From Millerton to Coleman Station

May, 2018 by thisworksforme

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.

Accordion

Old Croton Aqueduct Trail

From Yonkers to Ossining

May, 2018 by mb.provenzano

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.

Charter Oak Greenway

Bolton Bridge

May, 2018 by gfoote

Looks like the bridge over Rt 6 in Bolton is finally going in. Connection to the Hop River Trail this Summer?

Larkin State Park Trail

Great trail,non -paved

April, 2018 by tuckereb

Just got my new gravel bike and this trail was a perfect bridal (horse) trail ride.Mud ,cinder,dirt and gravel are what you will encounter ,but the high berms,ponds and deep woods experience are worth the trip!

Hop River State Park Trail

beautiful trail

April, 2018 by markhill718

This trail is beautiful in the fall. Well maintained and mostly paved. Its a smooth ride but gets a bit rocky crossing between bolton and vernon. Other than that this trail is amazing. Can be a bit crowded on weekends though

Air Line State Park Trail

Flooded trail

April, 2018 by blueskye

After heavy rain on April 16th, the trail along the Willimantic River is temporarily flooded and impassable,

Charter Oak Greenway

Inline Skaters Beware

April, 2018 by fencinggirl93

I am fairly new at skating, so I am always on the lookout for nice trails to try. Near the park itself, the skating is great. It is fairly smooth, has nice wide paths, and only a little bit of hill. As I went further from the main park however, it was almost entirely up hill, and there were several bridges that may not be too bad normally, but they are rougher and have lips that prevent just coasting onto them. On this particular day it had snowed recently so while the paths were dry, the bridges were covered in slush and very hard to do anything but carefully walk on while holding the railings. It took me a long time just to go half a mile because of the slope and bridges, and then when I decided to turn around, the hill was so steep, I frequently had to go into the grass to avoid going too fast. Normally I would just ride hills like that out, but the path was rather curvy, and there always seemed to be a rough bridge at the bottom. My brakes were useless. If you are an advanced skater, this may be a fun challenge, but for me, it was more trouble that it was worth. Nice park/trail for other purposes though.

Setauket-Port Jefferson Station Greenway Trail

First timer!

April, 2018 by dsiry

Went for the first time yesterday. it was beautiful. Nice and wide, not over-crowded. some hills for a bit of a challenge and best part is that I was able to bring my fur baby in a safe walking environment . .

Setauket-Port Jefferson Station Greenway Trail

very safe plenty of hills good visibility nice and wide

March, 2018 by t13

very safe plenty of hills good visibility nice and wide

Briarcliff-Peekskill Trailway

not well maintained

March, 2018 by brian144

I started at Watch Hill Rd near the shooting range, over the Croton Gorge, and up the road. The trail continues across the street but it’s hard to find and doesn’t look like a trail. It heads through Tea Town and is very nice for a few miles. Once you get near Rte 134 it’s a mess. Apparently it continues for another mile or two but I turned around at 134. Very nice in spots, especially when all the trees are in, say May-June.

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