Looking for the best trails around Madison?

Explore the best rated trails in Madison, CT, whether you're looking for an easy walking trail or a bike trail like the Windsor River Trail and Niantic Bay Boardwalk . With more than 46 trails covering 345 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

Moosup Valley State Park Trail

Great Little Trail!

April, 2025 by 9q8skpdwwc

I rode the Moosup Valley Rail Trail a few days ago from Moosup to Oneco. The trail is in excellent condition all the way, and beautiful! I rode 34mm knobbies, but would have had no trouble on 28 slicks. The only irritants were a guy on a motorized scooter in Moosup and 2 guys on screaming dirt bikes going the other way a bit farther along, but they passed quickly. In Sterling, dirt bikers had dug shallow ruts into a short stretch of path, diagonal to direction of travel, which made it bumpy but not hazardous. Otherwise lovely! I wish Rhode Island would step up to the plate and finish the connector to its Washington Secondary path.

Farmington Canal Heritage Trail

A few signs hold it back from five stars

April, 2025 by robert.richter89

I rode the entire northern section of the Farmington Canal Trail from Plainville into MA on a windy Easter Sunday. The trail itself is fully paved, in very good overall condition (there are a few bumps and cracks but nothing major). Simsbury offers a great stopping off point to get refreshments just a quick turn off from the trail. The scenery changes from light industrial parks, residential, marshes, a little farmland and some nice wooded areas.

I have one complaint that prevents this from being a five star trail. The signage could be better. There are times in the more urban areas that I lost the trail, a quick look at Google Maps got me back on and I never was too lost. There are a few signs that were helpful so just a few more would make this a five star trail.

Cheney Rail Trail

Cheney Trail

September, 2024 by nicoleh742

Hubby and I discovered this trail last fall. We absolutely love it. It's a beautiful hike with all the leaves changing. Great for pets too as it's a pretty flat walk. It's def longer than 1.7 miles though. I love that the leaves are changing we will be frequented this trail alot during this fall season!

Accordion

Cheney Rail Trail

Cheney Trail

September, 2024 by nicoleh742

Hubby and I discovered this trail last fall. We absolutely love it. It's a beautiful hike with all the leaves changing. Great for pets too as it's a pretty flat walk. It's def longer than 1.7 miles though. I love that the leaves are changing we will be frequented this trail alot during this fall season!

Setauket-Port Jefferson Station Greenway Trail

Great path but the abandoned warehouse is gone so seeing old building aspect gone, and they are not maintaining with the roots pushing up the road

September, 2024 by jrfarrell1991

Great path but the abandoned warehouse is gone so seeing old building aspect gone, and they are not maintaining with the roots pushing up the road

Moosup Valley State Park Trail

What an improvement!

September, 2024 by bopflu

When I attempted this trail in 2022, I called it "the worst ride of my life." I got covered in mud, and the numerous puddles teemed with mosquitos. But what a difference two years made!

The trail has been vastly improved, now offering a highly pleasant ride through Connecticut's Route 14 corridor. It does, however, become rougher shortly after you cross Route 14-A near the Rhode Island state line. I only hope further improvements will be made.

Air Line State Park Trail

We had a great ride! 6.6 miles. Beautiful day!

September, 2024 by susanmazur13

We had a great ride! 6.6 miles. Beautiful day!

Moosup Valley State Park Trail

Horse

August, 2024 by janeyac1

Love the beautiful trail, but horseback riders should have a manure bag on the horses to catch their droppings. Not fair to others walking the trail.

Maybrook Trailway

weeds weeds weeds!!!

August, 2024 by johnjr4

This is a great trail that is now suffering from neglect . The weeds are so overgrown that the trail is almost down to a single lane.

Moosup Valley State Park Trail

It’s nice!

August, 2024 by revgil

When I first rode this trail in 2012, it was horrible, even though I had a mountain bike. My wife and I just settled on driving over to Coventry, RI to ride; Moosup was next to impossible. But several months ago work began to get it fixed up. What a nice job, with drainage, a new stone-dust surface, and nice fencing. We have ridden trails all over town country, and this is one of the nicest anywhere. Now, if RI will finish the Washington Secondary Trail from Summit to the state line, I could ride all the way to Providence without having to go on the road!

North Shore Rail Trail

great trail

August, 2024 by gatogo4

Easy riding trail. Lots of crossings There are no center posts on some of the crossings making the crossings much easier to navigate. Hope the rest of the center posts could be removed

Mattabassett Trolley Trail

What's the point....

August, 2024 by jbarrett01

......of having a trail where there is nowhere to park???

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.