Find the top rated running trails in Pittsfield, 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 trail seems little-used. Rode a gravel bike starting at the parking lot at the south end. Several trees down in the trail and some puddles and running water (to be fair, it had rained the night before). The trail surface varies and while it’s manageable, this isn’t a trail for someone looking for a leisurely rail trail cruise. Nice views of the Connecticut River.
The entry leads you to believe there is a 9 mile asphalt trail linking two towns in a Vermont valley with just a small gap near the north end. Unfortunately, there is no such thing. The trail is a very confusing series of blue signs which go through the woods on dirt (mud) tracks, over grass lawns with no identifiable trail, and on busy and narrow town roads (the only asphalt on the trail). Talking to locals, we discovered that parts of the trail are used for mountain biking, but that the idea of a continuous trail linking West Dover and Wilmington is a dream that has yet to be realized.
My wife and I rode this trail from one end to the other. The scenery was beautiful, the ride was easy and the people were nice. Lots of lake views. Some hills but not difficult. Parking was a small challenge but not impossible. I would do it again in a minute.
Stayed at the nearby HGI and decided to take the advice of the front desk lobbiest and run the river path. Entered the path by crossing over the ped bridge by the BHF. Soon into the run the path was closed, It looked like the construction was there for some time leaving me to believe the path had been closed for a while. Turned around and went south dodging the overgrowth along the paved path. A few miles lated it terminated. So, u-turned again back to the BHF bridge. Suspect the city has no budget to invest in maintenence. Too bad. Nothing special, but a least I get out there.
From Wassaic to Copake, free parking in Wassaic train lot on weekends. Goes through a few small towns with bike shops including one in Copake. Lots of places to eat in the towns, some country roads tie the rail trails together, a few hills but nothing brutal, beautiful lake, plains, and frams views, and if you don't mind a small hike, check out Bash Bish falls in copake, worth the hike.
November 2017
It was a good trail in the mountains, except for the bumps of leftover railroad ties. One end is a nice train station, the other is North-South Lake Campground, which you can also bike around, but is not a part of this trail. To see the wonderful water fall you have to get off the main trail a very short distance. A nice bridge over a creek too. Yeah, mountain bikes with suspension only.
I rode this last November, during a warm dry Sunday afternoon. It's a fine trail. At one end is a closed ski slope and lodge I think should become a mountain bike downhill business. The other end just seems to ... end on a road. Between is some nice mountain pass, at one point along a creek that wants to eat the trail, so there was a chainlink fence. If you're in the area, go visit this trail and the charming village of Tannersville.
I rode the trail last week starting at the Wassaic Metro-North station (free parking only on weekends and holidays) and ending at Orphan Farm Road. I did continue to Hillsdale but as there was no signage to indicate how to find the newest section from Hillsdale to Black Grocery road, I did it on road.
All-in-all, both of the main completed sections are in very good shape, fine for road bikes. For the on road gap I took Route 22 going north (flatter but fairly busy with high-speed traffic) and the Under Mountain Road- Rudd Pond Road Route (hillier but much less traffic with swimming available at Taconic State Park- Rudd Pond) on my return. The roads were in good shape either way.
Bash Bish Falls State Park off the northern section is well worth the minor detour. Stay on the road to the falls parking lot and in a 1/4 mile (up hill) you're in Massachusetts!
Went to the south access point in Warehouse Point and found no parking lot, no sign, and no trail! Drove through the building construction only to find a fence blocking the trail. So I went to the north end in Enfield and that too was blocked with a locked fence. No sign or other way to know it was closed. Hope someone will keep the status updated in the future!
Although this Bike Path is scenic, it is NOT maintained, it is continues wide cracks in the pavement and huge bumps. I already saw a couple bickers fall because of the neglected pavement. Not only do you risk a fall because of the neglect, you also risk damage to your tires as the bumps & cracks are severe. I have a Road Bike, and changed my tires because of the bumps, also note the bumps also can shift your gears.
Well worth the 1 1/2 hour ride to get to!! We started at the Plainville parking area and decided to take this path to Simsbury and then return the Farmington Canal Path. The River path is beautiful and deserves the 5 stars. It runs along a beautiful river and brought us to the quaint little town of Collinsville. The only issue we had was the path came to an abrupt end at the route 202 & 44 intersection. There were no signs to indicate the street riding. Guessing , we proceeded on the street until we saw the cycling insignia. The only other poor signage is when you come out of the state forest and there is no indication until approx 100 yards that tells you that you're going in the right direction. We were glad we had the Rails to Trails Southern New England Guide Book we could keep referring to!
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