Hickey and Peeskawso Peak Loop is a 2.8 mile heavily trafficked loop trail located near Stockbridge, Massachusetts that features beautiful wild flowers and is rated as moderate. The trail offers a number of activity options and is accessible year-round. Dogs are also able to use this trail but must be kept on leash.

Length2.8 miElevation gain685 ftRoute typeLoop
Dogs on leashKid friendlyCampingCross-country skiingHikingNature tripsSnowshoeingBird watchingRunningForestViewsWildflowersWildlifeRockyScramble
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The term squaw is considered universally offensive by Indigenous groups in America due to its use for hundreds of years in a derogatory context. Indigenous activists have continued to work both locally and in more general educational efforts, to rename the locations across North America that contain the slur, as well as to eliminate the slur from the lexicon in general. See here for more info: https://en.wikipedia.org/wiki/Squaw#Efforts_to_rename_placenames_and_terms_with_squaw_in_them

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Reviews (701)
Photos (657)
Activities (655)
Completed (1,329)
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Dennis Ross
Yellow StarYellow StarYellow StarYellow StarYellow StarYellow StarYellow StarYellow StarGray StarGray StarApril 22, 2021
Hiking

Had a little snow this AM but it was fine.

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Joni Traficante
Yellow StarYellow StarYellow StarYellow StarYellow StarYellow StarYellow StarYellow StarYellow StarYellow StarApril 19, 2021
HikingGreat!

Great hike. Beautiful views. Counterclockwise provides a little more strenuous hike and less traffic

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Julianna Broche
Yellow StarYellow StarYellow StarYellow StarYellow StarYellow StarYellow StarYellow StarYellow StarYellow StarApril 18, 2021
Hiking

Great hike! Easy to follow/well marked, great views, crazy rocks at the top. We went on a Sunday and it was decently traveled but not too bad. 6$ parking and decently difficult hike on the way up. I recommend going counter clockwise for a more challenging hike.

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Stephen Fromm
Yellow StarYellow StarYellow StarYellow StarYellow StarYellow StarYellow StarYellow StarYellow StarYellow StarApril 18, 2021
Hiking

Beautiful views. On a dry day, footing is not too challenging.

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Sabina Perkins
Yellow StarYellow StarYellow StarYellow StarYellow StarYellow StarYellow StarYellow StarYellow StarYellow StarApril 15, 2021
Hiking

Wet hike!

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bob davidson
Yellow StarYellow StarYellow StarYellow StarYellow StarYellow StarYellow StarYellow StarYellow StarYellow StarApril 10, 2021
Backpacking

Plenty of people in a Saturday but not toooooo crowded. Take the unmarked trail where the monument overlook splits off to see the old man on the mountain (MA edition)

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Hilary Russell
Yellow StarYellow StarYellow StarYellow StarYellow StarYellow StarYellow StarYellow StarYellow StarYellow StarApril 8, 2021
Hiking

Great hike up the Hickey Trail past a few little waterfalls and then the steeper trail up the Squaw Peak for incredible views-to the North to Mt. Greylock and to the west to the Catskills in NY. It is quite rocky going down from this point on the Peeskawso Trail down so care is needed. There were hawks flying around at the top and lots of bird activity on the Catskills view side. Not to many people but it was a weekday. Not recommended for people not in great shape but you can take lots of rest stops along the way and eventually get to the top. Worth it for the incredible views at the top of Squaw Peak.

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Alex Kogan
Yellow StarYellow StarYellow StarYellow StarYellow StarYellow StarYellow StarYellow StarYellow StarYellow StarApril 5, 2021
HikingGreat!
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Mackenzie Wyman
Yellow StarYellow StarYellow StarYellow StarYellow StarYellow StarYellow StarYellow StarYellow StarYellow StarApril 4, 2021
Hiking

Great trail! Beautiful views.

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Larry Ginsberg
Yellow StarYellow StarYellow StarYellow StarYellow StarYellow StarYellow StarYellow StarYellow StarYellow StarApril 3, 2021
HikingGreat!

Great! Well marked all the way. Good elevation to get the heart rate up a bit. Wonderful views from the top. Nice to have a sandwich on the boulders and look out over the Catskills. Really good Covid escape!!

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Emily Povich
Yellow StarYellow StarYellow StarYellow StarYellow StarYellow StarYellow StarYellow StarGray StarGray StarMarch 31, 2021
HikingGreat!

Great hike! It got our heart rates up and was well marked. The trees and vegetation were beautiful. One part of the trail ran along side Rt 7, there was not a clear view from the top.

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Lisa Dempsey
Yellow StarYellow StarYellow StarYellow StarYellow StarYellow StarYellow StarYellow StarYellow StarYellow StarMarch 27, 2021
Hiking

Excellent views!

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Layne Kasprzyk
Yellow StarYellow StarYellow StarYellow StarYellow StarYellow StarYellow StarYellow StarYellow StarYellow StarMarch 27, 2021
Hiking
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Richie Jay
Yellow StarYellow StarYellow StarYellow StarYellow StarYellow StarYellow StarYellow StarYellow StarYellow StarMarch 24, 2021
Hiking
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Alexa Delacqua
Yellow StarYellow StarYellow StarYellow StarYellow StarYellow StarYellow StarYellow StarYellow StarYellow StarMarch 23, 2021
HikingFeeGreat!

Wonderful trail and easily marked. it's a simple loop so no picking and choosing different trails to take. the hickey trail had a tiny amount of ice and some mud but nothing too bad to traverse. by the end of this week it should be completely clear. the outlook is amazing. The quartz rock everywhere is beautiful and something not seen everywhere in a such a large amount.

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Gary Lefebvre
Yellow StarYellow StarYellow StarYellow StarYellow StarYellow StarYellow StarYellow StarGray StarGray StarMarch 21, 2021
Hiking

Great 3 mile hike

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Rebeccca Mokey
Yellow StarYellow StarYellow StarYellow StarYellow StarYellow StarYellow StarYellow StarGray StarGray StarMarch 20, 2021
HikingGreat!IcyRockyScramble

Beautiful trail loop with gorgeous lookouts. There were a lot of parts with steep rock steps/stairs. The trail started and ended next to a busy road, which wasn't relaxing, but most of it was in peaceful woods and the lookout points were serene & stunning.

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Jane Carpenter
Yellow StarYellow StarYellow StarYellow StarYellow StarYellow StarYellow StarYellow StarYellow StarYellow StarMarch 20, 2021
HikingIcyRocky
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Rudá Fabiano
Yellow StarYellow StarYellow StarYellow StarYellow StarYellow StarYellow StarYellow StarYellow StarYellow StarMarch 20, 2021
Hiking
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Adam Ludvigson
Yellow StarYellow StarYellow StarYellow StarYellow StarYellow StarYellow StarYellow StarGray StarGray StarMarch 14, 2021
Hiking

Nice, relatively easy hike with good views from a few overlooks. I took Indian Monument Trail up (blue) and then the Hickey trail down (yellow). For right now, I would recommend the opposite; Hickey trail is very icy and muddy, tricky to descend. Spikes definitely recommended.

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Chris Western
Yellow StarYellow StarYellow StarYellow StarYellow StarYellow StarYellow StarYellow StarGray StarGray StarFebruary 28, 2021
Hiking
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Carol Brunelle
Yellow StarYellow StarYellow StarYellow StarYellow StarYellow StarYellow StarYellow StarGray StarGray StarFebruary 26, 2021
Hiking

Didn't realize I didn't actually start recording until I reached Devil's Pulpit Outlook.

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Lily F
Yellow StarYellow StarYellow StarYellow StarYellow StarYellow StarYellow StarYellow StarYellow StarYellow StarFebruary 20, 2021
HikingGreat!Snow

Lovely trail with some very impressive views. Would recommend spikes at the moment! Note that parking costs $5 and can be paid for with the machine in the parking lot.

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Jill Gaulding
Yellow StarYellow StarYellow StarYellow StarYellow StarYellow StarYellow StarYellow StarYellow StarYellow StarFebruary 15, 2021
HikingGreat!Snow

Not too mobbed on Valentine’s Day! Took yellow up, red across, then came back the long way via blue. Great views at the top; only a little scary for those of us afraid of heights!

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