Explore the most popular 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.

hiking

views

nature trips

forest

Cheshire, Massachusetts Map
VIEW FULL MAP
hiking
blowdown
muddy
9 days ago

Nice hike, beautiful views, pretty easy but steep at parts. A little difficult going down if you have bad knees. It was poorly marked and confusing depending on where you parked. We ended up on the loop by accident and the GPS on All Trails wasn’t very accurate. Pay attention to the marks and make sure you know which road you parked on.

Spectacular little out and back with an amazing view to reward you at the furthest point. It doesnt hurt that I was lucky enough to see it at about the peak of autumn color. Uphill all the way and a nice relaxing cruise back down to the parking lot. Highly recommended.

hiking
28 days ago

Very nice well marked . Some markings in rock so snow would hide them .

hiking
28 days ago

Park at bike trail and walk on road as part of AT. There is an out and back which is recommended over the loop as loop is very uninteresting. Cobble views are very nice approximately 1 mile on the trail. Very mild grade.

Took Jones Nose and AT to Greylock summit, then a detour to Robinson's Pt (just half a mile out of the way with a great Vista), then the Overlook Trail down to the Hopper and CCC Dynamite trail back to Jones Nose Trail. Just over 9 miles total. Favorite parts were Jones Nose Trail with the beautiful meadow, the first couple miles of the AT, and Robinson's Pt. Very quiet and peaceful until you reach the first road crossing (where you can drive further up the mountain and park) it gets very crowded with kids and families. Greylock was a madhouse, as expected on Columbus day. Hopper Trail and CCC Dynamite trail were very quiet and easy, yet underwhelming compared the AT section. The latter is a much older forest.

hiking
30 days ago

Great beginner loop! Got us motivated to begin hiking Sunday’s and moving on to more moderate hikes.

Fantastic foliage viewpoint! GPS takes you incorrectly to furnace hill road. Trailhead parking on right hand side of NOTCH Rd. in Cheshire. Enjoy amigos.

It is a tough hike, and the first 1.1 mile is very steep. There are multiple road crossing points. I did it during the columbia weekend with the hope to see fall colors. I did see the change of colors, but the trail itself is not very impressive. I would say only two spots are worthwhile for pictures - the little house where the pond is located and the peak. At the peak, I realize you can drive all the way up there. Also, the temperature difference is huge (very cold and windy at the peak).

Steep but short. Worth it

Started at the Notch Rd trail head this go around! Loved the water at the base! Foliage was good not quite peak! The front half of this hike is steeper than the full AT portion of this hike.

Highly recommend this trail, the meadow at the beginning is stunning! The ridge makes for a very nice moderate trail.

Another beautiful day in the Berkshires. Great weather and the foliage is starting to look colorful.

hiking
1 month ago

Good easy weak. Great views.

hiking
2 months ago

Pretty easy trail if you go the right direction! We accidentally started on the wrong side of the road but once we got on the right trail it was as advertised.

Not exactly sure why this hike is rated “hard” — I’d maybe rate it moderate, but certainly not hard. Initially there’s a steep incline but it doesn’t last for too long and evens out after a little bit. Stays relatively flat until right before the summit, where it gets a little steep again. Beautiful summit views with a lodge, bathrooms and WW1 memorial. Descent is mostly flat with some steep-ish inclines that could prove a little difficult for some people. Overall very nice hike, would recommend.

hiking
over grown
rocky
2 months ago

This was a great hike! I would stop short of calling it “hard”, but it was a bit challenging. The initial ascent isn’t all that long, and once you hit the AT, you’re essentially ridge walking for a long time - gentle ups and downs. The last .75 miles is a bit steeper, and pretty rocky, but short. Views are obviously worth it. The Hopper Trail and CCC Dynamite Trail were totally empty of people, and pretty rocky, but no scrambles. The Dynamite Trail is overgrown in places. Wonderful hike.

We took two cars and did the hike one way (south bound) instead of the loop. It was honestly great - there really wasn’t any drastic elevation gain along the trail and I personally think this hike would be fine for beginners. Even for a Sunday at noon, we had no problem finding parking at the Jone’s Nose trail head, but you do have to pay for parking at the north summit of this trail ($10). A majority of the trail was shaded, and even after some rain there wasn’t much mud. The only part we got turned around was at the fork towards the end where you come off the AT and get on the Jone’s Nose trail - make sure to look 360 degrees around at any forks so that you don’t miss any signs (more my fault than the trail’s). I would absolutely do this again, especially with my dog.

hiking
rocky
scramble
3 months ago

This hike was of epic proportions ... I read the reviews of steep ascent so I was prepared. I would say 1.5 mile of uphill rock scramble. Super technical after that .Continues to ebb and flow between ascents and descents. Quite frankly, when you just aren’t sure how to gauge trail because uphill is so steep, .5 seems much longer. Hiking part of Appalachian Trail .Getting to the summit became an undeniable goal. I had to get to the top . So amazed once I got to summit as the view is stunning. Not much time to linger as we had to get down the mountain and it would take sure footing. I would recommend this hike to experienced hikers only. In the end we were so proud of our accomplishments , it made the pain go mostly away as we came off the mountain.

hiking
3 months ago

Quiet peaceful. Two nice views. Little muddy at times

hiking
muddy
over grown
3 months ago

We followed this AllTrails map for our entire hike, and at no point were there any rocky scrambles or parts that I would consider difficult, and nothing technical whatsoever. We parked at the lot where Rockwell meets Adams Road. At 7:30am on a Saturday, we were the first car in the lot. The lot's capacity is significantly reduced right now due to two giant piles of gravel, so bear that in mind if you're planning a late arrival. We took the Jones Nose Trail marked for the Appalachian Trail and summit. It was very easy to follow the worn path and blue blazes. Sure, the first mile was steep but we knew to expect that. Once we picked up the AT (white blazes), it was less steep and more rolling but gradual hills. Lots of log walkways to protect the plant life in areas that I assume get very muddy when wet. We did experience a fair bit of mud on parts of the trail with no walkways, but no bugs at all! We followed the AT all the way to the summit, then returned via the AT until it meets the Hopper Trail (blue blazes), then took that to the CCC Dynamite Trail and eventually back to the intersection of the Jones Nose Trail and the AT to return to the parking lot. There was no one else for the first 2 miles of the hike. A lot more people seem to park further up the mountain and pick up the trail there. Of course the summit was crowded - it was a chilly, blustery but beautiful sunny day, so not as crowded as I imagine it could be. A few people were on the Hopper Trail but we never saw a single soul on the Dynamite Trail, so that was really nice. I could see a few footprints in the mud but it's very obvious this is one of the trails less traveled - there was a lot of overgrowth and parts that felt like bushwhacks but it was great to experience so much peace out there. We finished with a total of 8.5 miles that included lots of exploring at the summit. By the time we returned to our car, the lot was completely full and someone had to wait for us to leave while other cars gave up waiting for spots. All in all, this hike was much easier than I expected and apparently much more gradual that the Thunderbolt and Bellows Pipe trails, but also a lot less crowded which is always my preference.

Quick easy hike with a nice view.

hiking
3 months ago

Markings are a little confusing in places as we almost went down the mountain on a different trail but the GPS helped. Nice easy hike though

Load More