Explore Appalachian Trail: Massachusetts: Best Day Hikes - view hand-curated trail maps and driving directions as well as detailed reviews and photos from hikers, campers and nature lovers like you.

This month marks the 80th anniversary of the #AppalachianTrail, which passes through 14 states from Maine to Georgia. . With so many access points along its approximate 2,190-mile route, this trail is not only an excellent option for thru-hikers and section-hikers, but also day-hikers and those looking to escape into nature for a few hours. . To honor the Appalachian Trail, we have compiled a list state by state of some of our favorite day hikes along the AT. Check out this list for Massachusetts and help us celebrate the legacy and natural wonder of this trail!

Appalachian Trail: Massachusetts: Best Day Hikes Map
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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 views from the Pine Cobble junction and Eph's Lookout. Street parking is plentiful along Massachusetts Ave, near the start.

Super pretty in late November. Perfect for a 6 year old and non-hiking 13 year old. Great mix of forest meadow and streams.

Jogging - it's a beautiful trail to run on . Varied terrain and a great mix of woods and open meadows!

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.

Great trail and great overlook! The trail from start of the main road to the overlook is 2.4 miles.

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.

Glad to have gotten out today to do this trail because it was such a beautiful day, but I definitely wouldn't rank it as hard. Views were good but not as mount-onus as I had hoped. I walked the road for a bit afterwards and enjoyed the views from there much more than from the other side. Decent hike overall.

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.

Lovely walking, although parts of the trail aren't kept up well, but the view from the "look out point" is excellent. About two miles near the end of the trail is on a road, which was a nice respite from the brush and bugs.

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

good hike for fitness. beautiful look out and had lunch at the pond. people were eating lunch and swimming. came across a rattle snake on the way back down....made excellent time back to the car following that!

hiking
6 months ago

Very beautiful trail. Well maintained except in literally 1 part about 70 feet worth of trail out of the 3.3 miles that we hiked. Impressive. Gorgeous scenery throughout. We hit many little bridges, stream crossings, mountain views, meadows, deep woods, rocks, clear trail, uphill, downhill, flat plain. All around fabulous! Took us around an hour to do the 3.3, no stopping.

used AT to summit rated strenuous half quarter mile up, but more moderate to me..spectacular views from the top

Right near Lee and a great workout. Beautiful forest and trail.

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!

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