Explore the best rated trails in Monterey, MA, whether you're looking for an easy walking trail or a bike trail like the Albany-Hudson Electric Trail and Black Bridge Trail . With more than 64 trails covering 834 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.
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.
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.
Rode the two sections of this beautiful trail today. From the parking spot in the middle of the Ware trail towards Gilbertville is a nice ride along the river. But a short one. Opposite the old factory the trail suddenly ends and there are handwritten signs "Stop, Don´t go further, Private property..." It would only take a few yards to reach the next road to travel on towards Gilbertville. No chance. Shame on you, property owners! (The trailmap shows a way through, but that might be an error?)
Okay, same way back and on to Route 32 past Gilbertville, where the next trailhead is waiting;-)
Smooth surface, well maintained and even good for kids bikes and flat all the way to Wheelwright. 3 nice old bridges. This is one is fully recommended! Absolutely worth it.
I rode the entire 24.7 mile southern portion of the Harlem Valley Rail Trail on a beautiful fall day. The HVRT offers everything you could want from a trail experience: a fully paved surface, mostly flat, beautiful scenery (especially in the Fall) and a perfect mid-point trailhead to grab a bite to eat.
I don't recall seeing any water fountains along the trail although the trailhead in Millerton offers many options for places to eat or resupply. The HVRT offers a myriad of scenery changes from farmland, quiet streams, distant hills to quaint towns. I have ridden many paved rail trails in the past and the HVRT is one of the best with almost no surface imperfections for the entire distance. There are many trailheads along the entire trail giving many distance options. All this adds up to a perfect trail in my opinion!
Map is 6 months out of date
Rode the full trail on a glorious October Saturday. the views were spectacular, peppered with fiery fall leaves. The trail is in incredibly good condition over the whole length. Such a lovely ride.
Part of this trail is closed, my wife and I got about 2 miles or so in and there was a detour sign for the trail and we could not find where it picked up again. Road on the streets for a bit and then headed back to the truck, got about 5 miles in on the ride so not a total loss
Started 3 miles south of New Paltz & ride all the way to Kingston , plenty of places to eat & drink in New Paltz after that there is a farm brewery on your right going north & a little health food eatery in the middle of nowhere by a campsite on the left going north after that you come to get Rosendsle trestle , the mining caves ( you can feel the cold air mass as you ride by ) Once you get to Kingston you pedal via rroad to the town
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!
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!
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