AT in the Berkshires: Greylock Edition

Leaders
Andy Tu (Leader), Monika O'Shea (Leader)
Program
3-season hiking
Type
Hiking
Trip date
Saturday, November 7th
Difficulty rating
Backpacking, L4 hiking
Prerequisites
backpacking experience and moderately strong hiking ability required (generally equivalent to two L3/L4 trips back to back)

Tired of the I-93? Want to hike within (mostly) the boundaries of the Commonwealth? Come with us to the Berkshires for an overnight backpacking trip over Mt. Greylock, the highest peak in Massachusetts at 3,489 feet. We will utilize one of the luxurious MA AT leantos to catch the end of leaf peeping season, warm our hands over a campfire, and hike a lesser traveled section of the AT.

Route:

We have a few route options depending on weather:

  1. Point to point from Cheshire, over the Greylock summit, stopping at Wilbur Clearing Leanto for the night, and finishing just over the VT border for 21 miles and 5800ft vert total over the two days.

    If the weather is too cold/snowy on Greylock itself, then:

  2. We'll head a bit farther down south, starting from the Mass Pike and hike through Tyringham with an overnight at the Mt. Wilcox North Leanto for a total of 20 miles and 4000ft vert.

Fitness/Experience Requirements:

This trip is open to moderately-experienced backpackers. This should not be your first time backpacking - backcountry camping experience is required - nor should it be your first experience hiking in New England. You should be a moderately strong hiker, able to hike at least two >7mi days in a row with a heavy pack and comfortable with steep and rocky New England terrain.

Note that this period of shoulder season can start getting cold overnight. We'll try to keep everyone warm and happy, but if you know you hate being any amount of chilly, this may not be the time to experiment. If winter actually sets in by this point in MA with significant snow, ice, or cold rain on both of our route options, we will likely respond by saving the trip for next year.

Gear:

We'll share a detailed packing list with folks on the trip. At minimum for yourself you'll need shoes, warm clothing including multiple layers, gloves and hat, food, water, headlamp, sleeping bag, sleeping pad, and a backpack to carry it all in. You can rent a cold weather sleeping bag, sleeping pad, tent, and large backpack from MITOC. Headlamps and Nalgene water bottles can be purchased from MITOC as well. We'll most likely share tents, stoves, and water filters amongst the group and can organize this closer to the trip.

Costs:

You can expect to pay for your own food, your rental gear (see the price list here), and to chip in for gas/wear and tear for the cars (budget $30-50 for carpooling costs). Financial aid is available for MIT students, please save receipts.

Lottery:

Please note that being selected in the lottery does not guarantee you a spot on the trip. We may shuffle the list at leader discretion based on car availability and if the trip is a good fit.

view from November, 2021 leanto on AT MA 2021


Signup

Algorithm
lottery
Maximum participants
7
Signups open at
Oct. 21, 2026, noon
Signups close at
Oct. 30, 2026, 9 a.m.
Notes
  1. Any dietary restrictions?
  2. What is your backcountry camping experience?
  3. Do you have experience camping in cold (30F range or below) weather, whether backcountry or frontcountry?
  4. What are two harder hikes you've done recently? Please include rough distance / elevation gain.
  5. What do you want to learn or gain on this trip?
Signups for this trip are not yet open.