Find the top rated running trails in Montauk, whether you're looking for an easy short running trail or a long running trail, you'll find what you're looking for. Click on a running trail below to find trail descriptions, trail maps, photos, and reviews.
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This is a multi use bike trail for everyone to enjoy.
Was visiting the area and am so happy I got my gravel bike out to do this trail. As others have mentioned, it is very, very well maintained and quite smooth, enabling fast riding (I rode the entire trail as listed). As a former rail, this trail has nice and gradual elevation changes and has cool features like the tunnels and bridges. I'd highly recommend and hope to be back for another spin soon.
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
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
I took a ride on a gravel bike from Putnam to Willimantic and back yesterday. I crossed the bridge in Putnam from Kennedy Drive (a nice paved path there along the north shore of the river!) to pick up the Air Line, which my map app shows as starting there. Though there were some short bits of various trails there, none of them went anywhere. I ended up back on roads and made my way to Town Farm road where the Air Line commenced, with signage. However, the next several miles were very rough, and I would not recommend riding there except with a balloon tire mountain bike with front and back suspension. But from the Pomfret Station on to Willimantic, it was either beautiful, or at least fine, except for some road crossing s with very steep and rocky ramps on both sides. For most riders, those ramps have to be negotiated off the bike. But overall, I had a great experience!
July 19 2025
Just rode from Pomfret west to the Rt6 overpass. Most of the trail is good riding except for some rocky sections, but the overgrowth is starting to close off the trail in sections. It is down to just one lane. It would be nice if the state could mow the weeds.
I rode 20.5 miles of the southern section of the Air Line Trail from East Hampton to Willimantic on a very hot day in June. This section of the Air Line Trail offers gorgeous scenery, peaceful seclusion and a tightly packed gravel surface that is in very good condition throughout. Despite the heat the trail is very shaded which provided much needed relief from the sun. There are a fair amount of road crossings, most are very small, quiet roads and all of the busier roads have warning lights that can be activated to let motorists know you are crossing.
The only two small complaints I have is there is a lack of signage along the trail. There is one very short on road section that I almost missed getting back on the trail due to there being no signage, I just rightly assumed the small unmarked path on the road was the way to get back on the trail. The gates at the road crossings are on the narrow side which can make navigating through the road crossings difficult. I feel these two issues do not at all detract from what this section of the Air Line Trail has to offer.
I recently rode this on a cool day in May from Manchester to Willimantic and back, so right at 40 miles. The trail is well-maintained and foot/bike traffic was light, even though it was a holiday weekend. Very scenic for long stretches and low elevation gain. I rode a gravel bike with 45 mm tires. On a road bike with reasonable tires, this should be do-able (I saw a couple of them), but there is one rough section of about 100ft (30m) where you would need to walk. There is also one underpass that is dark enough to use a headlight...but it's passable if you slow down. There are a number of places to read about the history of the rail line, as well as a few locations with fix-it stations with bike tools and air pumps.
One final tip: Google maps takes you to an intersection on Colonial Road for the Manchester trailhead...the parking lot has a tiny sign that is easy to miss.
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.
This is my childhood bike path, it’s a lot shorter than I remembered now that I have the speed and endurance I do. Still a wonderful ride through the swamp and forests of south Kingstown, through peace dale and wakefield , to the beaches of Narragansett.
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