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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Reviews (744)
Photos (3753)
Andrea Evans
Yellow StarYellow StarYellow StarYellow StarYellow StarYellow StarYellow StarYellow StarYellow StarYellow StarThu Jul 09 2020
Walking

Hiked the full loop (4 miles) including upper and only saw one other pair of hikers. Peaceful. Moderately buggy in the wooded paths as expected. Fields full of butterflies and dragonflies, with lovely views . Trails in good condition. Nice for a meditative nature walk.

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Kate S.
Yellow StarYellow StarYellow StarYellow StarYellow StarYellow StarYellow StarYellow StarGray StarGray StarMon Jul 06 2020
Hiking

We did this hike on a Monday mid-day and only saw two other people. Nice hike for the kids - steep at the top, some rocks to keep it interesting. Trail was well marked and in good condition. The parking as described above (on the side of Notch road) does not correlate with the starting point of this hike. We drove to the starting point and there's no parking allowed. There's a sign that directed us to park over by the local post office, which was maybe 0.3 miles away. I dropped off the kids and then swung back - took me about 10-12 minutes total because I jogged back. There is parking on the side of notch road, but it's not clear from there how to meet up with the AT. No directions and on the app, there doesn't appear to be a path. Other thing is definitely enjoy the Viewpoint because the top has barely a peek through.

Emily Boardman
Yellow StarYellow StarYellow StarYellow StarYellow StarYellow StarYellow StarYellow StarGray StarGray StarMon Jul 06 2020
HikingBugsRockyScramble

I didn’t believe the reviews on how hard this trail was... I really should have. I went to Mt Everett and Mt Race then turned around (about 20k in total over 7ish hrs, 6.5 moving). Maybe it was the heat and humidity but my pace was far slower than normal on a trail this length with this elevation. Lots of rocks to scramble on - I recommend trail runners or boots for extra grip. This trail starts with a dirt incline - this type of incline is common along this trail (often times with rocks involved too), so I recommend basing how far you go on how you manage that initial hill.

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Taylor Eagen
Yellow StarYellow StarYellow StarYellow StarYellow StarYellow StarYellow StarYellow StarGray StarGray StarSun Jul 05 2020
Hiking

Quick but steep hike with awesome views at the top.

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michele wolf
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BugsRocky

This is on the moderate side of hard. Nothing technical, no scrambles, but steep in spots and unrelenting on the hike up. Trekking poles help the old knees on the way down. Trails are well marked. No view at the top, but if you take a right onto the AT at the end, it's an easy walk over to Pine Cobble for a gorgeous view from the rocks. We made it a loop by taking the Pine Cobble trail back down and connecting to Class of 89 and back to Chestnut. Your legs will burn a bit and your blood will be pumping on the ascent, but this team of a 54 year old and a 58 year old enjoyed it. And we're still alive.

James Kocaba
Yellow StarYellow StarYellow StarYellow StarYellow StarYellow StarYellow StarYellow StarYellow StarYellow StarThu Jun 25 2020
Hiking

Intermediate hiking for sure. Rocky, rooty with some climbs.

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Austin Ryan
Yellow StarYellow StarYellow StarYellow StarYellow StarYellow StarYellow StarYellow StarYellow StarYellow StarTue Jun 23 2020
Hiking

The trail actually took us around Saddle Ball Mt and then we reached the Appalachian Trail/Cheshire Harbor Jct. After summiting Greylock we took the Appalachian Trail South pretty much all the way back. If you are interested in AT hiking then this is a good little taste of what it’s like — up and down the ridges with no end insight haha!

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Emily Eyre
Yellow StarYellow StarYellow StarYellow StarYellow StarYellow StarGray StarGray StarGray StarGray StarSun Jun 21 2020
HikingBugsOver grown

Arrived to find signage stating the trail is closed. It’s possible I was starting from a secondary trailhead. Kiosk looked newly built but the trail appeared overgrown.

Tim Burrows
Yellow StarYellow StarYellow StarYellow StarYellow StarYellow StarGray StarGray StarGray StarGray StarWed Jun 17 2020
Hiking

Benedict Pond is very attractive, but the rest of the hike was just all right. There was only one spot with a great view, and it is not clearly marked on the maps; I sort of stumbled into it. Mostly it is rolling hills going thru well forested land. Mount Wilcox and Beartown Mtn are just big hills, if you are on these trails anyway. Some sections are muddy and the area is used by dirt bikers and mountain bikers. If you want some nice forest walking tho, this should satisfy you. There are lots of pines, beeches, birches, maples, and something that looked like young tulip trees, but I didn't see any mature tulip trees around. Bring some bug spray if it is in the warmer months.

Mercy Coffman
Yellow StarYellow StarYellow StarYellow StarYellow StarYellow StarYellow StarYellow StarYellow StarYellow StarMon Jun 15 2020
Hiking

Loved this trail. If you wanna see the whole hike in a video (watch at highest picture quality): here’s the link: https://youtu.be/SfNTYedIEso or check out Explore More - Appalachian Trail on YouTube. The white trail markers are what you need to stay on and it can be a little hard to see at times. Just keep going in an upward direction! Totally worth it. Our dogs had a blast on this trail and we only saw one family as we were first coming in. Light traffic right now! Perfect time to go!

Shreyas Ram
Yellow StarYellow StarYellow StarYellow StarYellow StarYellow StarYellow StarYellow StarYellow StarYellow StarSun Jun 14 2020
HikingRocky

Great short hike with a decent incline which our 2.5yr old loved to climb for a few minutes and then sat down back in her toddler carrier. Great for kids and dogs. The peak has spectacular views of the Greylock mountain area

Sam Collette
Yellow StarYellow StarYellow StarYellow StarYellow StarYellow StarYellow StarYellow StarGray StarGray StarWed Jun 10 2020
HikingBugs

Nice, but waterfall is a stream. Still a beautiful hike, and quiet. Dirt road for about 20 minutes to get to trail.

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Kelsey K.
Yellow StarYellow StarYellow StarYellow StarYellow StarYellow StarYellow StarYellow StarYellow StarYellow StarTue Jun 09 2020

this is the Appalachian trail from cheshire to greylock. correct map, wrong name. This hike was super cool. some steep past especially in the beginning. but amazing views. we went one way from the rail trail parking in cheshire and then came down greylock to finish. 11 miles overall. its a decent challenge and its so cool to see the mt from a distance and approach. cute places to peek out! The breeze was phenomenal. just busy when we got to the top!

Comment from AllTrails

- 1 month ago

Thanks for your feedback. This trail has been edited and updated to reflect the comments in this review.

Mike McConnell
Yellow StarYellow StarYellow StarYellow StarYellow StarYellow StarYellow StarYellow StarYellow StarYellow StarSun Jun 07 2020
HikingRocky

I am lucky enough to live near it and it is a great go to trail when I don’t have a lot of time. The picture from the overlook says it all

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Anne Arent
Yellow StarYellow StarYellow StarYellow StarYellow StarYellow StarGray StarGray StarGray StarGray StarSat Jun 06 2020
HikingBugsRocky

This was a nice trail, but it didn’t really have a “wow” factor to it. We went early, so it was quiet until the end when several groups passed us as they entered. It was a nice walk, but I’m not in a rush to go back. Bring the bug spray!

Kelsey K.
Yellow StarYellow StarYellow StarYellow StarYellow StarYellow StarYellow StarYellow StarYellow StarYellow StarMon Jun 01 2020
MuddyRocky

I wouldnt call this "hard" but say its steady upward and has a few tricky and rocky spots. I worried a few times about the ankles! lots of pretty plant life. we continued and followed this to the long trail. The partner stated a few times "not a ton of views". i didnt mind, but if its really important to you, just head up and turn to go see pine cobble during your hike. it started to hail and we still managed to make good time safely down the return even at the rocky parts.

Sean Jennings
Yellow StarYellow StarYellow StarYellow StarYellow StarYellow StarYellow StarYellow StarYellow StarYellow StarSun May 31 2020
Hiking

Great

Kimberly Kaigle
Yellow StarYellow StarYellow StarYellow StarYellow StarYellow StarYellow StarYellow StarYellow StarYellow StarSat May 30 2020
Hiking

I really enjoyed my hike on the AT today up to the vista on Prospect. Many beautiful shots and I captured the smallest toad I have ever seen. I stopped for a quick rest to soak in the views looking over Williamstown and the Mountain Ranges of NY and VT. After a quick snack I continued on the AT heading East and took the road back down to the Reservoir until I came to the AT trailhead where I began. The trails were clear and there was a nice breeze all day to keep the bugs away!! Great hike and a shout out to all the trail crews across the country for maintaining the trails!! Thank a You!!

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Ryan Knapp
Yellow StarYellow StarYellow StarYellow StarGray StarGray StarGray StarGray StarGray StarGray StarThu May 28 2020
Hiking

The AT part of the trail is great the rest of the hike is on an ATV/dirt bike road and is muddy and uninteresting, not really a hiking trail.

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Ali Baker
Yellow StarYellow StarYellow StarYellow StarYellow StarYellow StarYellow StarYellow StarYellow StarYellow StarMon May 25 2020
Hiking

Gorgeous trail. Beautiful wild flowers, fun wildlife. The dog adored it.

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Kelsey K.
Yellow StarYellow StarYellow StarYellow StarYellow StarYellow StarYellow StarYellow StarGray StarGray StarMon May 25 2020
HikingRocky

went up to mt Everett and contined on the AT until we met the sign for race brook trail then headed back. not for the faint of heart. definitely will take some effort to get up. had a beautiful picnic and many great continuous views. In all the hiking in the berkshires this had the largest open panorama. the pine needles can be slippery. definitely a lot of effort, especially the rock stairs, but taking it slow, was worth it.

A NB
Yellow StarYellow StarYellow StarYellow StarYellow StarYellow StarYellow StarYellow StarYellow StarYellow StarMon May 25 2020
HikingBugsRocky

I am super confused! I planned a 6:30 h trail to bear mountain AND back, but me and my partner (we’re both in great shape, run 10k twice or three times a week (he also bikes) and hike one day in the WE) were only half to bear mtn after 4-5 hours (we stopped one hour for lunch). So weird! So we went back and had to walk a bit in the dark. I think it’s 6h30 just to one point and not back. My bad! Haha

Jeffrey Vigliotti
Yellow StarYellow StarYellow StarYellow StarYellow StarYellow StarYellow StarYellow StarGray StarGray StarSun May 24 2020
Hiking

Surprisingly challenging hike. We did it out and back as a two day backpacking trip.

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