Explore the most popular nature trips 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.

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!

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
9 months ago

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.

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."

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.

This is a nice trail to do. I hiked this trail as a point to point and not a loop like some people do. The first mile from the trailhead is the hardest and steepest part of the hike. Once you're on the AT, the hike pretty much levels out except for some minor inclines and declines. I arrived at the summit early, but as I was doing my decent the trail was getting crowded. Be careful while hiking this trail, because you have to cross the road 2x and watch out for drivers.

Google maps via this app brings you to the end of Furnace Hill Road, a residential area with no parking sides on both sides of the street. Can someone please post where the parking is for this hike?

hiking
Friday, June 17, 2016

Quick and easy trail. Two scenic vistas.

It was fantastic

Sunday, May 15, 2016

when you get to the red arrows pointing back the way you came, follow them backward and around to the left away from the AT for about 100 ft.

Gorgeous view and perfect workout

The scenery was beautiful. The hike was very pleasant. Will do it again for sure. Had a awesome picnic on the top of the cobble looking out at Cheshire Lake.

Great views. Got lost on the way up. Follow single white markers not the double when you come to the fork.

hiking
Monday, November 02, 2015

Beautiful hike with amazing views

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