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

beautiful views. Rocky.
difficult in winter.

Nice hike, kinda crowded.

12 days ago

Went for a 4 mike hike around the trails of Cat Rock on Hale Reservation. Only recorded the beginning 1.5 miles around the area for Cat Rock. Then I detoured straight for Noanet Pond and enjoyed the picnic bench by the water. I took the paved path down and back around the reservation. It was snowy and quiet on this off-season day. Multiple options for windy paths, or paved paths. Beautiful lake and interesting features to look at.

30 days ago

The view was worth the hike

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.

1 month ago

Love this place. Camped here for years and always hiked the trails. Now live closeby to hike every weekend. Way more trails that are not listed here. Enjoy!

Made it to where the AT splits off before having to turn back because of time. Beautiful ridgeline during the ascent, and great views to the west once the climb is over. A bit of ice in the steeper sections but nothing microspikes couldn't handle. Lot at the AT trailhead holds about ten cars.

Nice views from the Pine Cobble junction and Eph's Lookout. Street parking is plentiful along Massachusetts Ave, near the start.

1 month ago

Trail around Lake Rico’s edge is amazing, not listed as a trail but just follow the water line, there’s a narrow trail alongside it. Best trail in the park

3 months ago

Hiked this trail in the wintertime following a snowfall and was not disappointed. Tough to believe you can find a serene landscape like this tucked inside the I-95 corridor! Great views and well-marked trails, with a few rocky/scrambling areas and several challenging inclines and descents. Good footwear is a must. Will hike the longer variation next!

3 months ago

Kids friendly. Wear good shoes

Started out from the trailhead on Patterson Road, the AT goes steeply up for the first mile or so, then moderates as you go higher on the ridge. Mt prospect trail deviates to the right passing a couple of beautiful open spots where the views toward the Taconics and Williamstown open up.There is a large Cairn at the summit, then the trail starts to drop down. You do get views of the Greylock summit in the distance. We went on a cold day and it was brisk along the ridge as the air speeds up as it goes over the mountain, but the views were beautiful and very different from most hikes on Greylock that offer views toward the Adams side mostly. We were out about 3 hours which makes a nice half-day hike.

Magnificent trail

4 months ago

Great fall hike!

Very easy going section of the AT.. I was able to walk it this fall, very scenic..

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.

I suspect this hike would be easier going the opposite direction, Cheshire to Dalton, as you would spend more time on the descent after Gore Pond. But, having the "reward" of hanging at the Cobbles at the end is nice as listed.

Nice property but very rocky and full of tree roots too...be careful. The large ledge is impressive as is the miniature railroad track thing. Very cool. Farley Pond was dry but there was a cute deer in there. Very nice property but lots of rocks, I'm lucky I didn't trip and fall.

trail running
5 months ago

A nice little trek turned into a 5+ mile loop through Hale Reservation. I've never been to Cat Rock so thought I'd check that out. Pretty cool ledge in the heart of the Reservation. Plenty of alternative ways to do this hike/trail run. Enjoy!

Start on Skyline Trail South to the Elliot Tower and finish Skyline Trail North. All the views will be near the end of the hike, about 3/4 of the way through, which is way more rewarding. If you go counterclockwise, you'll see all the views at the beginning then nothing but trails for the majority of the way. Fun hike!

nice trail

on Great Blue Hill Trail

6 months ago

it was a beautiful veiw. it a must see.cant wait to see it in the fall

6 months ago

Great moderate climb. Well marked trail with beautiful views.

Parked at the Jug End Road trail head and hiked to the Mt Everett Summit. Loved this trail! Fantastic trail variation kept us interested and the many open vistas offered natural points to stop and catch your breath. We hiked up to the summit of Mt Everett first and then caught the loop around Guilder Pond back to the AT. Headed north to get back to our car. Finished about 10 miles in just over five hours. Would absolutely do this hike again!

Beautiful Section of Trail.


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.

beautiful hike me and my famiky were so happy to be together. i love them so much. best day ever. i wish dad was still alive

I have hiked rhis trail multiple times. including a double wish bone. it took me 2 times to get all the markers. the trail is marked. but not very well.

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