Looking for the best trails around Danbury?

Explore the best rated trails in Danbury, 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 88 trails covering 672 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.

Recent Trail Reviews

Walkway Over The Hudson

Walkway Courtesy

August, 2025 by wayne7532

Yes Walkway is wonderful, just one problem Cyclist Courtesy.
Have rode and seen a lot of cycling after 60 years, but never the lack of cycle courtesy that takes place on Walkway. Cyclist not letting one know that one is passing on left, or better yet on right, speeding, limit is10 mph. This is not just happing to slower cyclist but also when passing pedestrians. This also applies to the new E Bike presidents.

Hudson Valley Rail Trail

Great connector trail from New Paltz

August, 2025 by ddylla

This is a great paved trail that connects New Paltz to the Walkway Over the Hudson and then to the Dutchess County Rail Trail. Done together, you can ride for well over 60 miles if you want. The Hampton Inn in New Paltz is a great place to stay with the trail starting just across the street. The hotel also provides easy access to the Wallkill Trail.

Heritage Trail (NY)

Nice trail. Poor signage in Goshen

August, 2025 by ddylla

Overall, a very nice paved trail that’s well maintained but very poor connectivity and signage in Goshen. If not for that poor connection, I would have rated this trail five stars. Well worth checking out and hopefully Goshen will improve that stretch in the future.

Accordion

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

Heritage Trail (NY)

great trail , great maintenance , would recommend

August, 2025 by campinfool

What a wonderful ride , we did a total of 30 miles from Middletown to Chester and back ! Awesome trail wonderful maintenance of the trail!! Would recommend to anyone that wants to ride Loved the many Jonny on the spots and benches along the trail! As well as eating and drinks along the way to buy ! Even a bike repair station on the trail!!!! ¿¿¿¿ Kevin & Pat Bennett

Harlem Valley Rail Trail

Rural trail with outstanding surface

August, 2025 by andrix

Parked at northern end just S of Orphan Farm Rd, NY; Trail surface is outstanding including numerous portions of elevated sections over wetlands. Did not see much in the way of wildlife. Quite rural with the 1st p potty 10 miles south; Turned back at Millerton; Shade 50% or so.

Maybrook Trailway

The Weeds Are Gone

August, 2025 by robertgerry

I just rode the trail today and the weeds mentioned in a previous review have now been mowed and the tree leaning across the trail near Whaley Lake has been cut. The trail is now in excellent condition with none of the typical rail trail root bumps encountered today. BobG.

North Shore Rail Trail

Love the trail, but.............

August, 2025 by pawerfel

Great trail, ride it frequently with my wife. Good workout for 22 miles. Main issue is not the road crossings; we ride many trails with more crossings than this, but on those, the towns take down the brush and you can see cars approaching the intersections. On this trail, you pretty much have to stop and inch out into the road to see these cars, many of whom are not "impressed" by the flashing yellow lights that you need to push a button for. Many drivers are looking at their phones rather than the road these days. You must appraoach these intersections as if you are invisible. Be safe

Maybrook Trailway

Great Ride!

July, 2025 by douglas.klion

A friend and I did this ride today starting from Brewster to Hopewell Junction, continuing on the Dutchess Rail Trail for ~4 miles and back. The ride was excellent, a little over 50 miles with a gradual decent (~10 miles) on the way to Hopewell and ascent back. The trail was very smooth, there were a couple of spots on the Dutchess side that had growth into the trail and one downed tree blocking the way.

Wallkill Valley Rail Trail

great ride!

July, 2025 by v65xtm2gzt

Great ride through the shawingunk mountains ! Trail was great bikes were awesome ! What a beautiful day !!

Find Nearby City trails

Register for free!

Register for free with TrailLink today!

We're a non-profit all about helping you enjoy the outdoors
  • View over 40,000 miles of trail maps
  • Share your trail photos
  • Save your own favorite trails
  • Learn about new trails near you
  • Leave reviews for trails
  • Add new and edit existing trails

Get the Free TrailLink App

The trail is always better with TrailLink

Scan the QR code to get TrailLink on your phone

Explore by City

Explore by City

Explore by Activity

Explore by Activity

Log in to your account to:

  • View trail paths on the map
  • Save trails to your account
  • Add trails, edit descriptions
  • Share photos
  • Add reviews

Log in with Google

Log in with Apple

OR

Register for free!

Join TrailLink (a non-profit) to view more than 40,000 miles of trail maps and more!

Register with Google

Register with Apple

OR

Your account has been deleted.