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

Wasnt a bad trail. was foggy so views were bad. otherwise would have a bad view. summit was marked by cairn, with some decent outlooks along the way.

unfortunately it was foggy. otherwise there would have been some nice views. well marked, well kept.

Lots of mosquitos and a very wet path. I had to turn around after a mile or so because it just didn’t seem worth it. I drove to the top and yeah. It was so cloudy I would have been disappointed by all the effort I put in to get there. Bring bug spray even if you think you don’t need it and waterproof shoes if it’s been rainy.

I went on a perfect morning. Good vistas, nice burn in the legs going up and pretty easy walking on the way down. It took about 5 hours- spent about 45 minutes up at the top and took a few breaks.
It was steep at the beginning, but levels out quickly and I was surprised with how fast I got to the summit.

Love the walk. View is amazing! Turkey vultures are a site to see.

This is a short hike with lots of steep spots scattered throughout (nothing terrible). The trail markings are sad, but the rock features and view at the top are worth it.

???? My 12 year old son and I are relatively new to hiking but are in good physical condition. Is this % grade (10-15% at start, which I realize is steep) something that we can do without feeling totally trashed? We plan on heading out this coming Friday, 4/20. We have a goal of hiking Mt. Washington in mid-June and this hike is on our hit list for prep. Have a great day!

An all around great trail! Intermediate in difficulty. No need for micro spikes but poles are suggested. Runs 10%-15% grade for the duration of the trail. I'm glad we did it in the winter when the roads were closed so we did not have to encounter any tourist. With heavy stopping we completed the trail in 3.25 hours. The last part of the trail, once you get into the evergreens, is gorgeous! Cheers!

Short trip to the top and a bit steep, but very manageable. Can take anywhere from 30 min-1 hr to reach the cobbles, depending on level of fitness and break time. Great view of Cheshire Lake and Mt Greylock. Great spot for sunset too, just bring a light for the trip back down!

Good hike. Not sure why its listed as hard? Ive done this hike probably 20 times (Im local). It is 7+ miles, but not too strenuous. Cheshire to Dalton is a bit harder, because you do much more climbing, including climbing to the cobbles in the beginning. There is also a shelter with a privy about half way.

Nice hike. I'd put it more in the moderate category. I took the BRTA Bus to Main St in Dalton and walked to the trailhead on Gulf RD. Took me 4 hr 40 min (to the Cheshire Post Office bus stop) with 10 minutes at Gore Pond and 30 minutes at Cheshire Cobbles admiring the foliage finally coming in. Bus back to Pittsfield.

Definitely a must do climb if you are in the area. I would consider it moderate to difficult. I would not recommend for people with bad knees or ankles, heavy ankle support is recommended for everyone. Very rocky and lots of roots. The first 1 mile is a tough incline with steep elevation gain, pace yourself on that section, it's moderate after that point.

Park at the Ashuwillticook Rail Trail parking area, 41 Railroad St., Cheshire, MA 01225 (this address is how Google maps marks it, I don't know if the address is actually marked on the ground). It's across the street from the Cheshire Post Office. Parking is free.

It's a nice little hike, first through a residential area of a small town, then through woods most of the way. It starts out fairly gradual and gets a little steeper toward the end. The view of the surrounding mountains and valley dotted with small villages and a lake is lovely.

Hike directions: From the rail-trail parking lot, head east on Main St. You'll pass a giant "Cheshire Highway Dept." snowplow monument on the right, and then a small ice cream shop on the left. Where Main St. and East Main St. come in together, take East Main to the right, and in about 200 feet, turn right uphill onto Furnace Hill Road. Follow for about 1/3 mile until you see the white blazes turn uphill to the left, where there are woods on both sides of the street. The turn should be marked.

The route uphill is mostly quite wide, and starts out gradual. Follow the rectangular 2" x 6" white paint blazes on trees. Double blazes usually indicate a turn. If the blazes are offset (uneven) turn in the direction of the upper blaze. When you are almost at the end, you'll see a big rock outcropping. You'll continue past it, and then take a blue-blazed side trail that passes through mountain laurel a few hundred feet to the overlook. Enjoy the view, and return the way you came.

hiking
Sunday, August 13, 2017

This was the perfect, easy hike for the kids and I today. We were all a bit tired & hoping for something that was not overly taxing but still provided us with something worth-while to look at - this trail delivered. The trail is heavily trafficked (we were thankful to be the first on the trail, because we came across about a dozen other hikers on our way back) so it is not overgrown; it also is very well marked.

Hi; can someone please tell me the physical address to drive to the Cheshire cobble trail?

If you want to feel like Frodo bringing the one ring to the fires of mount doom, the trail between Saddle Ball and Mt Greylock can definitely help. The entire trail is beautiful and can be finished in 5 hours (with an hour break at the top of Mt Greylock). The top of Greylock is definitely a little crowded but only saw a handful of hikers on the rest of the loop. The views from the top are totally worth the trip and I even saw a bald eagle up there flying with the hangliders that use the Peak to launch from. Drove from upstate NY for this one and was not disappointed.

hiking
Friday, July 14, 2017

I hiked this on a misty, foggy day, which made Gore Pond (about halfway) look like that place where Yoda lives. The view of Cheshire from the "cobbles" was diminished, but still worth the climb from either direction. A fun 5 hours!

It is a great little hike from Furnace Hill Road. It is also a great spot to watch the locals fire off fireworks around the "forth."

Great hike with the 4 kids.

Beautiful view!!! Follow the white markers. Best to use GPS from alltrail app due to some of the trail is poorly marked.

hiking
Tuesday, April 25, 2017

Views were awesome!

*July 3, 2016*
I hiked this trail back in July 3 along with Mt Greylock from the Jones Nose trailhead. The only way that you know that you're at the summit is by carins that are placed there. The hike along the AT was pretty much flat with a few little ups and downs.

Great short hike! Not as steep as I would have expected. Took about 1.5 hrs round trip with 15 minutes at the top, and parking at the rail trail parking in Cheshire. No parking at trailhead. Return to Cheshire by AT North- white blazes, trail has a few turns so keep an eye for blazes. Views were awesome at the top!

hiking
Sunday, September 11, 2016

Short, steep trail leading to fantastic views to the north, west and south.

We used Rockwell Rd. Parking Area as our starting point and followed the Hopper Trail North until it met with Rockwell Road again on one of the many sharp turns. We crossed the road and followed the Appalachian Trail South to Jones Nose and the CCC Dynamite trail. back to the trail head on Rockwell Road. We chose to bypass Greylock Summit as we had hiked there the day before. Doing the trail this direction put the moderate climb at the front of the hike and the easier downhill part at the end of the hike. This easy hike offered very little in the way of Scenic Overlooks. It was a good follow up to the hard hike done the day before but offered little more than some exercise. If we had done the hike counterclockwise than the stretch of trail between Jones Nose and the AT would have been a real workout.

hiking
Monday, August 08, 2016

Parking area is on Notch Rd.

hiking
Monday, July 18, 2016

perfect for what it is...which is a short and easy mini hike with a surprisingly awesome view considering the lack of effort required to get there. This was my 5 year old's first experience on a trail and for that type of situation it was indeed perfect to get him into the woods with a very cool view at the end.

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