Explore the best rated trails in Longmeadow, MA, whether you're looking for an easy walking trail or a bike trail like the Southern New England Trunkline Trail and Ashuwillticook Rail Trail . With more than 53 trails covering 498 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.
I have ridden this trail from one end to the other! Parts are wonderful and parts washed out and muddy!
Beginning perhaps 2 miles north of the Simsbury Airport and continuing north for at least a few miles the trail will be closed for construction (looks like repaving + ?). I was on this trail yesterday and the "Will Be Closed" signs are abundant.
Love the scenery. There are plenty of rest areas.
I rode this trail from the Northern tip south about 10 miles and back. It was very smooth pavement, a well marked trail and delightful views.
Rode it Friday. The views were beautiful, the trail was in great condition, and the road crossings were not a problem at all. I’ll definitely be riding this one again.
I just rode the trail from Cheshire to New Haven Harbor. It gets confusing because of the lack of signage once you go under the Temple St Garage in New Haven. You get dumped out into a street and don't know where to go. The trail is on the road or sidewalk depending on what you prefer. Take a left onto Grove St. continue to the end and take a right onto Olive ST. Follow Olive St. to the end and pick up the trail again on Water St. Cross Brewery ST and take a right to continue on Brewery. Brewery changes to Sargent Drive. Take a left to go under I95 and the water will be in front of you. If you take a right and continue down for a little, along the water's edge, you will find dozens of food trucks to buy lunch before a return trip. It was well worth the trip.
As of 6/3/25 this trail is still closed south of 11th street.
There is a detour indicated, which we tried to follow, but quickly lost track of.
Found another way to access the trail further south, only to realize that we'd gotten onto the part of the trail that was officially closed.
I'm sure this will warrant a higher rating once it has re-opened, but we were more than a bit disappointed today.
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.
...we rode the western part... (is there a tool to edit a review?)
We rode the eastern part of the trail today, starting at the CT/MA border towards Douglas. The first 6-8 mls are well maintained and a good ride even with a street bike. Nice scenery, too. But then things get worse around Douglas. Rough surface with crushed stone, sand and deep puddles after a rainfall (like today). Looks like the track has not been maintained in a while and detoriates. A mountain bike is a big plus and highly recommended in some parts of the trail. Was a good ride though but do not expect a smooth one.
This is described as a 3.5 mile section but we only went about half way to the dam from the Stanley Mill. It is passable on bikes but has roots and larger stones along the stone path. It's really more a walking trail. The farm mentioned in the description was an interesting side visit and had very nice bath & water facilities. However, for a great biking experience the 10 mile section starting at Woonsocket is paved and a far more pleasant ride.
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