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◂︎ Mandy & Lexi's Massachusetts Adventures
Cheshire
Ashuwillticook Rail Trail
Date visited: 6/19/2022
See Also: Pittsfield, Lanesborough, Cheshire, Adams
This is another great multi-town bike trail, but don't ask me to pronounce the name of the trail. We started at the parking lot at the entrance to the Berkshire Mall, right on the border of Pittsfield and Lanesborough. We walked all the way up to the reservoir in Cheshire and back. It was just over seven miles total.
Ashuwillticook Rail Trail
Date visited: 9/29/2026
This is the section of bike trail from the Railroad Street parking area north to the Adams town line, where we left off earlier this month. The path is straight and easy, and runs mostly through a wooded area with some swampy ponds on either side. The fall foliage is nearing peak here, which seems like it's a few weeks early. It made for some nice color along the path. The highlight was the memorial to the large block of cheese near the parking area. I can't imagine what Thomas Jefferson did with 1235 pounds of cheese! It was mostly cloudy, but the sun popped up out occasionally, which was a welcome sight considering the three days straight of wind and rain before this. We wound up walking just shy of six miles out and back. We have more section in Cheshire left, as well as the southern most section of trail in Pittsfield left to do.
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Ashuwillticook Rail Trail
Date visited: 9/30/2026
Since the foliage was so great here the day before, we decided to come back the very next day and finish off the Cheshire section of the trail. Like the previous day, we started at the Railroad Street parking area, but this time continued south about three miles to the spot we left off at back in 2022. This is a very scenic section of trail, as most of the route runs along side the reservoir. There are a few small side trails that we checked out, as well as a fishing and picnic area off Farnams Road. The reservoir with the mountains in the background, along with the sharp foliage really, served to make this one of the more scenic stretches of bike trail we ever covered.
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Appalachian Trail
Date visited: 9/29/2026
A short "on-road" section of the Appalachian Trail runs along Main Street and crosses the Ashuwillticook Rail Trail. The trail blazes are actually painted on light poles along the road. We followed it for a bit, taking some photos of the signage, but didn't really make it to where the dirt trail starts up again. We have walked sections of this famous trail in Connecticut already, so we actually did hike the real trail before, but this was our first experience with the Massachusetts section.
