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Hickey, Squaw and Indian Loop is a 2.6 mile moderately trafficked loop trail located near Great Barrington, Massachusetts that offers the chance to see wildlife and is good for all skill levels. The trail offers a number of activity options and is best used from April until October.

Length 2.6 mi Elevation gain 688 ft Route type Loop
Hiking Nature trips Walking Bird watching Running Forest Views Wildlife
Description
Waypoints (0)

Note: 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

Weather
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Reviews (101)
Photos (320)
Recordings (87)
Completed (215)
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Judy Behrens
Yellow StarYellow StarYellow StarYellow StarYellow StarYellow StarYellow StarYellow StarYellow StarYellow StarSeptember 23, 2020
Hiking

North out of pkg lot red trail lower is doable

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Jessica Warren
Yellow StarYellow StarYellow StarYellow StarYellow StarYellow StarYellow StarYellow StarGray StarGray StarSeptember 19, 2020
Hiking

Great short hike!

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Annette Vanore
Yellow StarYellow StarYellow StarYellow StarYellow StarYellow StarYellow StarYellow StarGray StarGray StarSeptember 17, 2020
Off Road Driving

It was a little tough for me Great workout

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Daniel Abbey
Yellow StarYellow StarYellow StarYellow StarYellow StarYellow StarGray StarGray StarGray StarGray StarSeptember 15, 2020
Hiking
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Sandy Banzon
Yellow StarYellow StarYellow StarYellow StarYellow StarYellow StarYellow StarYellow StarYellow StarYellow StarSeptember 11, 2020
Hiking

I brought my 3 kids with me. We loved it!!

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Peter Dolcy
Gray StarGray StarGray StarGray StarGray StarGray StarGray StarGray StarGray StarGray StarAugust 17, 2020
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Tonya Maxstadt
Yellow StarYellow StarYellow StarYellow StarYellow StarYellow StarYellow StarYellow StarYellow StarYellow StarAugust 15, 2020
HikingFeeGreat!Rocky

Beautiful hike! Large rock formations and beautiful view. No bugs and dry! Stopped at Rio Cafe for breakfast afterwards- great find!

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Maureen O'Neill
Yellow StarYellow StarYellow StarYellow StarYellow StarYellow StarYellow StarYellow StarYellow StarYellow StarAugust 8, 2020
HikingFee

Well marked and maintained. A trustee met us in the parking lot and directed us where to park and gave us information on the trails. Not crowded but the people we met were all wearing masks. Beautiful views from the peak!

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Bryan User
Yellow StarYellow StarYellow StarYellow StarYellow StarYellow StarYellow StarYellow StarGray StarGray StarAugust 1, 2020
Hiking

Went on a Sunday morning it was fairly packed. $5 non member parking, honor system.

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Amber Cadorette
Yellow StarYellow StarYellow StarYellow StarYellow StarYellow StarYellow StarYellow StarGray StarGray StarJuly 27, 2020
Hiking

rocky, great workout

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Thomas Finney
Yellow StarYellow StarYellow StarYellow StarYellow StarYellow StarYellow StarYellow StarYellow StarYellow StarJuly 24, 2020
Hiking

Nice loop trail. The ledge along squaw trail is overgrown and need to climb up on rocks to obtain a clear view. Saw a large 250 lb black bear on Hickey trail on way down. Overall excellent well marked trail.

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Katherine Lewandowski
Yellow StarYellow StarYellow StarYellow StarYellow StarYellow StarYellow StarYellow StarYellow StarYellow StarJuly 23, 2020
HikingFee

My children (5 and 8) and I enjoyed this hike very much. Steep enough to be a little challenging but short. Lots of mushrooms, newts, and moths but not too buggy. Everyone we saw on a weekday put on masks to pass and observed social distancing. Would definitely come back.

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Olga Kim
Yellow StarYellow StarYellow StarYellow StarYellow StarYellow StarYellow StarYellow StarYellow StarYellow StarApril 20, 2020
HikingClosed

Closed until further notice due to covid-19

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Brian Krulish
Yellow StarYellow StarYellow StarYellow StarYellow StarYellow StarYellow StarYellow StarYellow StarYellow StarOctober 11, 2019
Hiking

Nice little hike!! Stopped on the way up route 7 on the way to Vermont...perfect spot to get out of the car and stretch the legs for a couple of hours. Great place for a family hike...not difficult

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Jennifer Corey
Yellow StarYellow StarYellow StarYellow StarYellow StarYellow StarYellow StarYellow StarGray StarGray StarOctober 2, 2019
Hiking

not a bad hike. great views at the top.

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Trisha G
Yellow StarYellow StarYellow StarYellow StarYellow StarYellow StarYellow StarYellow StarYellow StarYellow StarAugust 25, 2019
Hiking

We traveled up the Indian Monument trail, then up Squaw Peak and down Hickey. All of the trails are very well marked and maintained. There's a lot of foot traffic, but plenty of room to step aside or even share the trail with passers by.

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Jim Townsend
Yellow StarYellow StarYellow StarYellow StarYellow StarYellow StarYellow StarYellow StarYellow StarYellow StarAugust 18, 2019
Hiking

Be sure to take in the summit and trail along the ridge (orange to red to blue. Great way to spend a couple hours.

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William VanSant
Yellow StarYellow StarYellow StarYellow StarYellow StarYellow StarYellow StarYellow StarYellow StarYellow StarAugust 10, 2019
Hiking

Nice fun easy hike I grew up hiking, worth it, wait until it's not crazy though.

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Joe Miller
Yellow StarYellow StarYellow StarYellow StarYellow StarYellow StarYellow StarYellow StarYellow StarYellow StarAugust 4, 2019
Hiking

Great hike, don’t leave without checking out the Devil’s pulpit

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Carmel Farrell
Yellow StarYellow StarYellow StarYellow StarYellow StarYellow StarYellow StarYellow StarYellow StarYellow StarJuly 22, 2019
HikingRocky
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Marel Sitron
Yellow StarYellow StarYellow StarYellow StarYellow StarYellow StarYellow StarYellow StarYellow StarYellow StarJuly 11, 2019
Hiking

There is a $5 parking fee at the trailhead. Going up the red dot Squaw Trail was shady, rocky and a steep climb at times. We wished there had been more red dot markings along the way because it was a little confusing our first time. We took the easier light blue dot main trail to meandering down on a wide smooth path, which worked out really well for us. Monument Mountain was a beautiful, easy 2-3 mile hike with panoramic views at the summit.

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Emma Tanner
Yellow StarYellow StarYellow StarYellow StarYellow StarYellow StarYellow StarYellow StarYellow StarYellow StarJune 22, 2019
Hiking

Great trail with excellent views. Lots of history here. Will be back during peak foliage season.

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Steve Anderson
Yellow StarYellow StarYellow StarYellow StarYellow StarYellow StarYellow StarYellow StarYellow StarYellow StarJune 13, 2019

Great view

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Adriana Laser
Yellow StarYellow StarYellow StarYellow StarYellow StarYellow StarYellow StarYellow StarYellow StarYellow StarMay 27, 2019

some scrambling but beautiful views and forests!

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Alisa Band
Yellow StarYellow StarYellow StarYellow StarYellow StarYellow StarYellow StarYellow StarYellow StarYellow StarApril 25, 2019
Hiking

Note the elevation. Great walk!

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Paige W
Yellow StarYellow StarYellow StarYellow StarYellow StarYellow StarYellow StarYellow StarYellow StarYellow StarOctober 11, 2018
Hiking

This hike was nice, but very easy compared to what I had read here. This would be a fantastic trail run, but I was looking for a slightly more rigorous hike for walking than what I got. My friend and I hiked the more challenging leg of the trail up, crossed over the summit using Squaw Trail, then took the easier Indian Trail down (it’s better on your knees to go downhill more gradually). The paths were all incredibly clean and well kept. There were a few 4 year old kids playing at Summit when we got up there, which says something about how easy the hike is. Views are great, but if youre looking for more of a “real hike” where youre following blazes and needing to watch your footing, choose a different hike.

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Caitlyn Beck-Sabino
Yellow StarYellow StarYellow StarYellow StarYellow StarYellow StarYellow StarYellow StarYellow StarYellow StarOctober 8, 2018

My 8 year old daughter and I really love this trail, we did it for the first time back in April and didn’t make it to the top of the red trail but enjoyed our hike. Just went this past weekend (October) and made it up the red trail and down the yellow. Beautiful and only slightly challenging. View was amazing

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Charlotte Herzfeld
Yellow StarYellow StarYellow StarYellow StarYellow StarYellow StarYellow StarYellow StarGray StarGray StarAugust 8, 2018

Lotsa fun

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