Looking for the best trails around New Milford?

Explore the best rated trails in New Milford, CT, whether you're looking for an easy walking trail or a bike trail like the Hudson River Brickyard Trail and Walkway Over The Hudson . With more than 79 trails covering 609 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.

Best Trails in New Milford

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Showing 0 of 79
152 Reviews
Air Line State Park Trail

The Air Line State Park Trail winds 60.3 miles from the northeast corner of Connecticut, where the state borders Massachusetts, down to...

Length: 60.3 mi
State: CT
Surface: Ballast, Crushed Stone, Dirt, Gravel
20 Reviews
Ashokan Rail Trail

The Ashokan Rail Trail is an 11.5-mile multi-use trail that traces the northern edge of the Ashokan Reservoir, which provides a large...

Length: 11.5 mi
State: NY
Surface: Crushed Stone
4 Reviews
Ashokan Reservoir Promenade

With vistas of the Catskill Mountains and a vast blue lake, the Ashokan Reservoir Promenade is a paved pathway that spans just shy of 3...

Length: 2.7 mi
State: NY
Surface: Asphalt
1 Review
Billings Trail

Open in several disconnected segments, the Billings Trail is a dirt path that traverses a lovely scenic and wooded landscape outside...

Length: 3.3 mi
State: CT
Surface: Dirt
3 Reviews
Bloomfield Greenway Multi-Use Trail

The Bloomfield Greenway Multi-Use Trail currently runs 1.8 miles between Bloomfield and village of Tariffville in the Town of Simsbury. The...

Length: 1.8 mi
State: CT
Surface: Asphalt
12 Reviews
Branford Trolley Trail

The Branford Trolley Trail is essentially a 0.6-mile footbridge occupying an old bridge along the route of an abandoned trolley...

Length: 0.6 mi
State: CT
Surface: Concrete, Crushed Stone, Gravel
5 Reviews
Briarcliff-Peekskill Trailway

The Briarcliff-Peekskill Trailway is a 12-mile linear park that runs from the town of Ossining north to Westchester County's Blue Mountain...

Length: 12 mi
State: NY
Surface: Asphalt, Dirt, Grass
34 Reviews
Bronx River Greenway

The Bronx River Greenway runs for 22 miles along the Bronx River, traveling from the mouth of the East River north to the Kensico Dam,

Length: 22 mi
State: NY
Surface: Asphalt, Boardwalk, Concrete, Crushed Stone, Gravel
9 Reviews
CTfastrak Multi-Use Trail

A part of Connecticut's first bus rapid transit line, the CTfastrak Trail serves as recreational and multi-use path for walking and...

Length: 4.4 mi
State: CT
Surface: Asphalt, Concrete

Recent Trail Reviews

Governor Cuomo Bridge

Horrible surface, great views

August, 2025 by vbergerg_tl

While all are grateful that bike and pedestrian access were built into the new TZ Bridge, the rough bumpy surface is completely awful. Neither easy on the feet nor pleasant for bikes. I don’t know if it was like this a few years ago or was planned this way, but it’s disappointing.

Air Line State Park Trail

Willimantic to East Hampton - Just AWFUL!

August, 2025 by geminird

The claim of this being a 61 mile trail is very deceptive. Almost 40 miles of this trail is nearly unrideable except for mountain bikes (and even that would be unpleasant). We are experience riders and were on hybrid bikes with wide tires and front suspension. And while our plan was to cycle 40 miles from Willimantic to E. Hampton, we only did the first 10 mile section from Willimantic to James L. Goodwin State Forest.

The trail started out as just OK, but deteriorated in less than 2 miles. After crossing S. Brook Rd, the trail the trail was extremely gnarly and super overgrown. When we reached Goodwin State Forest, we were so happy to bail out and call it quits! Luckily, we had a SAG vehicle with us so we weren't forced to cycle back over the same awful trail.

Be warned, the entire trail we rode from Willimantic to Goodwin Forest was large, loose gravel, and the scenery is incredibly boring. There are places where the trail is extremely rough. At S. Brook Rd. the trail becomes unrideable, expect by maybe some die-hard mountain bikers. We used our SAG van to pop into other points along the trail from Goodwin to E. Hampton the trail only seemed to get even worse.

Honestly, just a really unpleasant ride.

Air Line State Park Trail

A Fabulous, Friendly, and Easy Trail !!!

August, 2025 by pedego2015

We (5) Friends Have Biked This Trail in It’s Sections from E. Hampton to Willimantic for Many Years. We Have Always Considered it to be 4-5 Star Rated, (For a Gravel Trail). Since 2015, We Have Switched to E-Bikes which makes the Trail 3x more FUN !! Having the Best of Both Sun & Shady Sections, It Has Only One small Section of about 300’ Near the Start leaving E.Hampton Where it’s sandy & .Loose

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