Explore the best trails near Pittsfield with hand-curated trail maps and driving directions as well as detailed reviews and photos from hikers, campers and nature lovers like you.

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Pittsfield, Massachusetts Map
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If you park at the trailhead, you'll need to walk 2.5 miles before seeing the beautiful lake shown in pictures. I recommend driving down and parking at the additional trail entrance a few miles in. This is much closer to the gorgeous view!

hiking
24 days ago

rails trails
1 month ago

Use the trail all the time. Gets a bit crowded in the afternoon, but head farther north (towards Lanesboro/Cheshire) and it gets less so. Glad to have this easy access resource nearby!

on Taconic Skyline Trail

4 months ago

cross country skiing
4 months ago

nice and flat !

some icy spots on trail, but that's expected for January. trail was well used today. disgusted by how many piles of dog poop there were.

hiking
7 months ago

The entrance to this trail is close to the end of the rest area parking drive.

We had some trouble finding the beginning of the trail. When you arrive at this location, it is a rest area, but there is not much signage about the trail. Unfortunately we went up the jeep trail/fire road to the right for sometime before realizing that we were not on the right path.

Once we got on the path, the trail was well-kept and it was a nice hike. It would definitely do it again.

Great hike!

Helhyyhmhjyyor jjj

walking
11 months ago

Really great hike to get outdoors and be able to hike for a few hours but I wasn't impressed with the top I was expecting more because I had hiked so far.