Watertown, CT Horseback Riding Trails and Maps

1045 Reviews

Looking for the best Horseback Riding trails around Watertown?

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

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Activities
Length
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6 Results
Activities
Length
Surfaces
Type

Air Line State Park Trail

54.6 mi
State: CT
Ballast, Dirt, Gravel

Hop River State Park Trail

20 mi
State: CT
Crushed Stone

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

26.5 mi
State: NY
Crushed Stone, Dirt, Grass, Gravel

Railroad Ramble

1.7 mi
State: CT
Asphalt, Dirt, Grass
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
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 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...
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
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...
NY 26.5 mi Crushed Stone, Dirt, Grass, Gravel
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...
CT 1.7 mi Asphalt, Dirt, Grass

Now, More Than Ever, Trails Matter!

During COVID-19, trails are being counted on as places where people can find solace and respite and we need your support to keep trails open and provide these critical FREE resources! Please continue to practice physical distancing and check the status of your trail before heading out!

Trails by activity

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....

Railroad Ramble

CT - 1.7 miles

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...

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...

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...

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....

Old Croton Aqueduct Trail

NY - 26.5 miles

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...

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...

Accordion

Larkin State Park Trail

CT - 10.8 miles

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...

Railroad Ramble

CT - 1.7 miles

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...

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....

Old Croton Aqueduct Trail

NY - 26.5 miles

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...

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...

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...

Accordion

Railroad Ramble

CT - 1.7 miles

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...

Larkin State Park Trail

CT - 10.8 miles

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...

Recent Trail Reviews

Harlem Valley Rail Trail

New sections open or nearly open

May, 2020 by billblum

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!!

New Milford River Trail

Beautiful and Fairly Easy

May, 2020 by lughnerson

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.

Jones Point Path

Fun and fine!

May, 2020 by graphographer

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.

Accordion

Windsor Locks Canal State Park Trail

nice quick ride

May, 2020 by nellyc1970

Decent trail.. gets quite busy. To many people constantly stopping on trail . Biking is tough there on a busy day. Better in early morning or evening.

Air Line State Park Trail

Section closed

May, 2020 by carrie.vezina

Section of the trail at Bull Hill Road is closed as well as the parking lot at this location. No information regarding why this section is closed or for how long. Would be nice if a brief sign could be posted to let users know if work is being done and how long the closure is projected to be. A lot of disappointed people driving and biking here; only to be turned around.

Old Croton Aqueduct Trail

Easy Trail Close to NYC

May, 2020 by kristibiglin

We only walked a small section of the trail starting in Dobbs Ferry. The OAC is lined with trees and has plenty of shade. It’s wide enough to keep social distancing (important these days). There are beautiful homes to look at along the walk. Great for city people who just want to make a day trip.

Putnam Trailway

Nice Trail!

May, 2020 by SPanny

My wife and I rode this trail on 5/16/20 from Brewster, NY south to the crossing with Rt 118 in Baldwin Place and back...about 24 miles total. The trail is in good shape, we enjoyed the views of Middle Branch Reservoir, Lake Gleneida, and Lake Mahopac. The trail runs through several towns like Carmel, but between towns it tucks well behind the roads to provide a really pleasant, through-the-woods experience. The trail does have some ups and downs...but none of them were too bad and it was nice to have a little variation from the typical "flat" rail-trail. The most significant "up" was from Brewster south during the first 5 miles or so. A little south of Baldwin Place the trail is a little rough and needs some work, but it's more than passable. All in all, very much worth a trip! Glad to see lots of people out on the trail.

Windsor Locks Canal State Park Trail

Windsor Locks Canal

May, 2020 by bktourer1

This trail may closed for a period of time which may change due to raptor nesting. You don't find out till you get there. You can also take the new path over the river to connect to Route 190 East to the shopping area, there are no signs telling you which way to go once you cross the Ct River

Columbia Greenway Rail Trail

Columbia Greenway Rail Trail

May, 2020 by CW4

Work on extending the Columbia Greenway Rail Trail is beginning at Main Street in Westfield. It is now 2.4 miles long and any extension will be greatly appreciated. The downtown extension insures that the new section will be heavily used. The rest of the trail is in excellent condition.

Farmington Canal Heritage Trail

beautiful ride

May, 2020 by deamerica1204

We rode our bikes all the to Southwick, Massachusetts.... what a beautiful ride. Paved trails and amazing scenery. Just asking for consideration if you are going to stop, pull of the paved trail. People tend to stop in the middle not giving consideration to the bikers, joggers and people walking

Air Line State Park Trail

Airline trail in Thompson CT

April, 2020 by kremillard88

Trail was awesome! Well maintained and nice views! Mainly flat except for hills at the road crossings. My family and I will definitely ride it again!

Air Line State Park Trail

Airline Trail - Pomfret Center to Putnum

April, 2020 by CW4

Just to keep trail riders informed, there is trail construction work ongoing from the Route 169 crossing in Pomfret to the Qinnebaug River in Putnam. Give it two seasons of construction and this 3 miles section should be done. IT includes 5 road crossings or bridges. That will be the last of the hard work on the Airline Trail.

Still needed is finishing the surface from Station Road in Hampton to South Brook Road at the Chaplin Townline (3.5 miles) and the 1/4 mile section from under Route 66 to the completed section of the Portland portion of the Airline Trail. Lastly, Portland has plans to begin design of the trail section from Camp Ingersol to Route 66.

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