Name: Cheshire Harbor Trail
Rating: 3.8

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Trail Ratings

3.8 from 6 votes

#6

in Mount Greylock State Reservation

#12142

Overall

3.8 from 6 votes

5 Star		17%
4 Star		50%
3 Star		33%
2 Star		0%
1 Star		0%

Trail Rankings

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3,937 Since Sep 14, 2017

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Mt Greylock starting point for the Cheshire Harbor Trail.

Jul 29, 2017 near Adams, MA

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Check-Ins

Oct 10, 2022

David Smith

I trailran to the top of Greylock and ended being #1 for the Greylock Ramble. 4.1mi — 1h 06m

Jul 7, 2022

Tiff C

Cheshire Harbor to AT connector to summit 6.5mi — 4h 25m

Feb 18, 2021

Chris Keavy

Tight snowpack. Microspikes were okay all the way to Greylock summit. Same for descent via Roaring Brook Tr. 3.1mi — 2h 00m

May 24, 2020

Lynne Hornyak

2.2mi

Nov 30, 2019

Erin Kiley

Oct 29, 2019

Joe Me

Several inches of rain during the past two weeks had made this trail muddy and wet and in some stretches like a flowing stream. But great cardio hike! — 1h 50m

Oct 6, 2019

Mark Daigneault

nice trail. beginning was wide. incline all the way to the summit. got very Rocky and craggy the further up you go. definitely a moderate hike. 6.4mi

May 14, 2019

Danny Deckers

Very snowy despite being may. Very beautiful 6mi — 3h 30m

Sep 4, 2018

Sara Aguirre

Warm day (average of 80 degrees). Very steep, many rocks and roots. Trail does not lead to the top of Mount Greylock. Careful, if heavy rain. 2.5mi

Aug 12, 2018

Sofia S.

6.6mi

Jul 29, 2018

Craig Gronlund

Nearby Recommended Routes

Mount Greylock Summit Loop

6.6 mi 10.7 km • 2,251' Up 686.23 m Up • 2,246' Down 684.66 m Down

Adams, MA

Microspikes recommended icy winter conditions (these crampons/ice axe are overkill).

Bellows Pipe to Mt Greylock Summit

5.8 mi 9.4 km • 2,231' Up 679.9 m Up • 2,231' Down 679.86 m Down

Adams, MA

Mohawk Trail Loop

5.1 mi 8.2 km • 1,133' Up 345.45 m Up • 1,119' Down 341.09 m Down

Charlemont, MA

Ledges/Overbrook Loop

2.7 mi 4.3 km • 894' Up 272.42 m Up • 898' Down 273.68 m Down

Lenox, MA

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Cheshire Harbor Trail

2.5

3.9

Point to Point

3,110' 948 m

1,551' 473 m

1,559' 475 m

0' 0 m

12%

19%