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Appalachian Trail: Cheshire to Mount Greylock

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Mount Greylock State Reservation

Appalachian Trail: Cheshire to Mount Greylock is a 7.1 mile moderately trafficked point-to-point trail located near Adams, Massachusetts that features beautiful wild flowers and is rated as difficult. The trail offers a number of activity options and is best used from March until October. Dogs are also able to use this trail but must be kept on leash.

Length 7.1 mi Elevation gain 2,903 ft Route type Point to Point

Dogs on leash

Backpacking

Hiking

Nature trips

Bird watching

Forest

Views

Wild flowers

Wildlife

Rocky

Waypoints (0)
Weather
UV Index
Daylight
Reviews (65)
Photos (364)
Recordings (43)
Completed (204)
Kelsey K.
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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.

Steve Ackerman
Yellow StarYellow StarYellow StarYellow StarYellow StarYellow StarYellow StarYellow StarGray StarGray StarSat Oct 19 2019
HikingMuddyWashed out

great hiking today! Some very steep climbs, but amazing views make the hard climbing worth it. Male sure you have good waterproof boots or a change of dry socks. A large section of the trail is essentially walking through a creek.

Avo Shahverdian
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HikingBlowdown
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Jack Mitchell
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Hiking

This is a great stretch of trail. Not *quite* as strenuous or rocky as, say, the Whites, but definitely a challenging hike. Some nice views on a clear day at the summit. I was a bit concerned about parking beforehand, but wound up grabbing a spot in the rail trail lot in Cheshire, which worked out well. It's about 0.4 miles from where you pick up the AT! From there, let the white blazes show you the way :)

Vic Chandhok
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HikingMuddyRocky
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Lisa Draheim
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HikingMuddy
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Evan Delmolino
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good hike but a few areas were really steep

Brittany Ionescu-Wolf
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Summited Northbound on day 5 of an AT section hike. Incredible pine and beech forests and so many wildflowers. The summit was astonishing and we were so happy to have planned to stay at Bascom Lodge to enjoy Greylock for a while.

Juan Yttesen
Yellow StarYellow StarYellow StarYellow StarYellow StarYellow StarYellow StarYellow StarYellow StarYellow StarMon Jan 22 2018

Great app love it

Amye P
Yellow StarYellow StarYellow StarYellow StarYellow StarYellow StarGray StarGray StarGray StarGray StarSun Aug 27 2017

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 mountainous 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.

Danielle Bucarey
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Hiking

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

Ann Bajart
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Hiking

Beautiful day. Minimal bugs Busy trail to the summit. Many friendly dogs. The food at the summit restaurant was fresh, home made and delicious. The views were awesome. Very pleasant hike. Not too hard in good, dry weather.

Joshua Redfern
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this trail will definitely exert you. quite muddy this time of year. bring plenty of water, protein snacks an extra pair of socks or good waterproof hiking boots. this trail utilizes some paths that are part of fresh water beds, so prepare for some wet, rocky sections. CELL PHONE SERVICE IS VERY LIMITED TO NONE AT ALL. bug-out gear suggested (emergency/survival kit) and rations should be on you.. . safety never takes a holiday so best be prepared. my brother and I were tracking quite large bear prints along a majority of the trail. approximately 5.5" paw patterns, some with signs of cubs... so be alert, be safe.. keep an open eye and ear.

thomas berry
Yellow StarYellow StarYellow StarYellow StarYellow StarYellow StarYellow StarYellow StarYellow StarYellow StarFri Apr 21 2017
Hiking

This was a fabulous hike for my son and I. We started in Cheshire - Outlook Ave. and hiked the AT to Mt Greylock. No crowds, no cars. More snow and ice than expected - the cold air felt good though. Great views since the trees had not yet budded. Descended via Overlook-Hopper-Dynamite back to AT. Made for a good long day. Plenty of sunny, rocky areas for my son to wait for me on the descent! Then hot curry in Williamstown that night was a perfect finish.

Geoff Garcia
Yellow StarYellow StarYellow StarYellow StarYellow StarYellow StarYellow StarYellow StarGray StarGray StarMon Mar 27 2017
Hiking

if you click the full map link on this page it'll indicate that the trailhead for this hike is around 275 North St. Cheshire, MA 01225. However, if you click the directions link it'll take you to the trailhead for the Thunderbolt trail. Given the mixup I don't have a review for the AT hike, but will drop one for Thunderbolt instead.

Michelle Baxter
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Hiking

Beautiful hike and we'll worth an afternoon.

Kaethe D.
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This was my first time on the Appalachian Trail! Started at Jones Nose for a great 4 mile hike to the summit. This is a very wooded trail that leads to the top of beautiful Mt Greylock with a summit overlooking the town of Adams, MA nestled in the valley.

Rebecca Ross
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Hiking

absolutely gorgeous

Anthony Manisero
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Hiking

Beautiful Oct 31 hike.Must see money falls and Prospect trail overlook

Dan Cabral
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Great way to spend a fall day

Maria Wishart
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Hiking

Think I picked the right one to review! Hiked from wilbur's clearing (Notch Rd) up the AT South toward Greylock summit. The first section between the parking lot and Mt.Williams is about 0.69mi and strenuous. The first 0.2mi is pretty easy then it just gets more difficult. Many step ups with rocks/boulders and step ups with roots. The view from Mt. Williams is gorgeous. After resting at the rocks head left to continue on the AT south toward summit. The hike lessens slightly in difficulty and intensity but this is when you will start really gaining mileage and and some elevation. Don't miss the outlook near the Thunderbolt Trail (blue sign w.yellow letters read The Big Bend). The last stretch from here to the summit intensifies again. Right before the summit road there are a set of steps the. Crossing the road the trail gets strenuous again for a short bit. Little further is the summit. It was definitely a tough hike (only been hiking for 6 weeks) but definitely gives you a sense of accomplishment. Round trip was 6.97mi.

Donald Pitale
Yellow StarYellow StarYellow StarYellow StarYellow StarYellow StarYellow StarYellow StarYellow StarYellow StarWed Oct 26 2011
Hiking

Didn't know where to start,found a parking area on the west mountain rd.My wife, two nine month old babies and myself did the ascent around 1 pm and made it to the top around 3pm.The temperature was mid 50's the top was in the mid 40's with a wind chill of maybe mid 30's. the descent was not as bad we made it back in an hour and a half,the trail up is hard and strenuous very!!!!

Abra R.
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Hiking
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Daniel Wheeler
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Hiking
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Sarah Aitken
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Hiking
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John McKenney
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Hiking
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Danielle Hadley
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Hiking
Stephen Kessler
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Hiking
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