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Appalachian Trail: Hiking the Berkshires

6 Days & 5 Nights 5 Read 1 reviews
  • Hike part of the 2,185-mile Appalachian Trail stretching from Georgia to Maine
  • Overnight in comfort, at a mix of hotel, B&B, and mountain lodge accommodations
  • Follow the AT’s famed white blazes through lush forests and rolling farm fields
  • Refresh your tastebuds with a hoppy New England style IPA
  • Explore the heart of the Berkshires, ‘America’s premier cultural resort’
Combine a section hike on the 2,185-mile Appalachian Trail with restful overnights in unique accommodations. Start and end your walk with visits to quintessential New England towns, where you’ll discover a blend of history, rugged practicality, and postcard scenery. Explore the Berkshires the slow way – on two feet – to find the gems hidden in the “Purple Valley.” Try out local flavors in Lenox, one of the Berkshire's cultural center. Then hit the trail as a northbound hiker, aka ‘NoBo’ in Appalachian Trail lingo. Spend three full days on the trail, following the white blazes north, including an overnight on the summit of Mount Greylock, the highest peak in Massachusetts. Culminate your Berkshires adventure with a day in charismatic Williamstown, offering not only unbeatable trail access, but also art, architecture, boutique shops and restaurants, and small-town friendliness.
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This iconic long-distance trail offers opportunities for hikers of all kinds, with the Berkshire Hills in the middle of the spectrum: challenging enough to provide a sense of accomplishment each day, but not as taxing or technical as the northern stretches of the Appalachian Trail. This moderate trip averages 5.5 miles and 1,100 feet of ascending each day, followed by an overnight in a charming inn or lodge. Try this tour for a taste of AT culture, camaraderie, and beauty, without forgetting that you’re on vacation!

Tour Style:

Self Guided | Go at your own pace on an independent tour.


Inn to Inn Walking | A classic point to point walking trip, staying in a different location each night

Ideal if you have an interest in:

Spiritual Journeys, Personal Growth, Historical Journeys, National Parks & Trails

As a guide, we would suggest that the minimum age of traveler this tour would be suitable for is: 5 Years


  • Classic

Activity Level & Terrain

The hiking on this trip is moderate, averaging 5.5 miles per day with an average elevation gain of 1,100 ft. Your second day of hiking will be the most challenging with a long ascent and little respite; however, the following day involves very little ascent and mileage is much shorter. Your final day, in Williamstown, is a loop walk from town, involving some sidewalks, paved roads, and dirt single track.


Navigating is easy using the Macs Adventure Navigation App. Your daily hikes will be mapped in the app with GPX tracks, route notes, and turn-by-turn directions. All of these resources are available to download for offline use, which is important as cell phone and Wi-Fi service are not reliable for parts of this tour. You will also have 24/7 telephone support from us here at Macs Adventure.

All navigation on the Appalachian Trail follows the trail’s white blazes and “AT” markers.

Experience & Fitness

The Appalachian Trail is well-established, thoroughly way marked, and highly traveled. However, conditions vary including mud, rocks, and tree roots. You should be accustomed to hiking for several hours at a time and will enjoy your tour much more if you are well-prepared. Some hiking experience is necessary, as there are not frequent access points and you will need to accomplish the day’s mileage in order to reach your overnight accommodations.


Stay five nights in comfortable accommodations, including a boutique hotel, a mountain lodge, and two B&Bs/inns. Although your lodging varies, all provide unique character, excellent service, and a warm welcome.

Single Rooms & Solo Walkers

This trip is based on two people sharing a room. If you’d like separate rooms, a single supplement is required. If you would like to request a twin room (same room with two separate beds), please notify us during booking so we can request this option; this may not be available in all locations.

If you would like to book this tour as a solo traveler, a solo supplement is required. The Appalachian Trail community is friendly, supportive, and it is common for hikers to undertake an Appalachian Trail adventure solo.


All breakfasts are included on this tour. Breakfasts will vary depending on your night’s lodging but may include a selection of hot dishes or a continental buffet, as well as coffee and beverages.

Lunches and snacks are not included. The Appalachian Trail is a wilderness trail and there are no restaurants along the route during days 2, 3, and 4 of your itinerary. Please plan accordingly regarding your timing and supplies. Consider picking up picnic provisions (meats, cheeses, bread, fruit, etc.) before leaving Lenox. Information about available food & drink can be found in your route notes.

One dinner is included at the Bascom Lodge on Mount Greylock (fixed menu, please provide any dietary restrictions at booking). All other dinners are not included; when in Lenox and Williamstown, you will have many excellent restaurants to choose from. On your overnight in Cheshire, you may order out from local options and dine at your inn.

Extra Nights

You may opt to add extras nights during this itinerary as there is plenty more to see, do, and hike. We strongly recommend spending an extra night in Lenox to take advantage of the local culture and day hikes. For further details and pricing, please ask us at the time of booking.

  • 5 nights in boutique hotels, B&Bs, or lodges
  • 5 Breakfasts & 1 dinner
  • Transfers to and from trailheads
  • Baggage transfer between accommodations
  • Detailed pre-departure information pack
  • Turn-by-turn route notes
  • Macs Adventure Navigation App for mobile phone
  • 24/7 telephone support
  • Donation to Appalachian Trail Conservancy
  • Travel to Lenox and from Williamstown
  • Lunches, snacks, dinners (except 1), and drinks
  • Personal equipment
  • Travel Insurance
  • Additional nights before, during, or after your trip
  • Airport transfers (if desired)
  • Hotel upgrade in Williamstown

When To Go

Although any time from May through October has its distinct advantages, there are reasons to go to the Berkshires in each season based on your goals. In the spring, from May through late June, the wildflowers will be in bloom along the trail, and tourist season isn’t quite in full swing so you can expect fewer trail users. High temperatures are in the upper 60s Fahrenheit, with lows in the 40s and 50s.

The summer months of July and August are lush, green, and often bring brief afternoon thunderstorms (always check the weather forecast before starting your hike and carry appropriate equipment!). Average high temperatures at this time reach the upper 70s, with lows in the upper 50s. September and October see a decrease in summer tourists, but they are quickly replaced by ‘leaf-peepers’, or those who have come to experience the brilliant fall foliage. Temperatures at this time of year are between the 40s and 60s Fahrenheit, with September tending to be a bit drier and crisper than October.


This trip is available from the last week in May through the third week in October. We suggest booking as far in advance as possible for a better chance at securing your desired dates. This tour is available to start any day of the week. However, due to minimum stay requirements on some weekends, we may need some flexibility in booking your accommodations.

Due to college events such as commencement and alumni weekend, there is very limited availability on certain spring weekends. It is difficult to begin the trip on a Friday due to minimum night weekend stays in some accommodations, though it may be possible. If you need to begin on a Friday, contact your Macs Sales Specialist and they can inquire.

An extra night in Lenox at the beginning is recommended as there are numerous highlights and lovely optional day walks.

Getting to the Start

Depending on where you are traveling from, there are several options to get to Lenox.

By Air: The nearest airports are Albany International Airport (1hr) and Bradley International Airport(1:15hr). We would be happy to arrange a private transfer from either directly to your hotel.

By Bus & Train: Peter Pan and Bonanza Bus lines both service Lenox, though schedules might be limited so we encourage checking your specific dates.

If you are coming from Boston or Boston Logan International Airport, you may elect to take the Amtrak Train's Lake Shore Limited Line to Pittsfield (4hrs), and then take a short transfer to Lenox. 

By Car: You can drive to Lenox by rental car, which you can drop off in Pittsfield (15min). If you take your personal car or would like to leave your rental in Lenox for the duration of your trip, please let your Macs Adventure Specialist know so that they can request this with the accommodation (not guarenteed, extra fees may apply). Driving times are as follows: Albany, NY - 1hr; Hartford, CT - 1:15hr; Boston, MA - 3hr; New York City, NY - 3:30hr.  

Getting from the End

We would be happy to arrange a private transfer to Albany International Airport (1 hour) or back to Lenox (50 min). There is also bus service to Lenox via the Berkshire Regional Transit Authority.

There are bus services from Williamstown to major cities with Greyhound and Peter Pan (check schedules).

Luggage Transfer

While you are hiking on the Appalachian Trail, your bags will be transported for you so that you can carry a small day pack with only the items you need for the hike. Everything else will be waiting for you when you reach your next accommodation (limited to one bag per person, no greater than 50 lbs). You may choose to remove bag transfers from your tour package and carry all of your belongings with you on the trail (in AT thru-hiker style)

General Information

Getting Around

Transportation from Lenox to the Appalachian Trail and from the trail to Williamstown is included in the tour (on Days 2 and 4). Otherwise, you will get around on foot. We are happy to advise you on your travel plans to and from the trip, so don’t hesitate to ask your Destination & Adventure Specialist.

Trail Donation

Book this trip and a $25 per person donation will be given to the Appalachian Trail Conservancy to support the outstanding work that they do to protect the trail.


Our pre-departure information pack includes a detailed equipment list on what to take with you. This includes warm and cold weather gear, hiking boots, rain gear, and lots of other specifics. If you have any questions about what to take, we'd be happy to share our own top tips and advice.

Travel Insurance

Travel insurance helps protect your travel investment, your belongings and most importantly you, from unforeseen circumstances that may arise before or during your trip. For more information, please visit our travel insurance page by clicking this link.

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Day 1 Arrive Lenox Day 2 Hike Appalachian Trail from Dalton to Cheshire - 8 miles 9 miles / 14 km Day 3 Hike Appalachian Trail from Cheshire to Mount Greylock - 8 miles 8 miles / 13 km Day 4 Hike Appalachian Trail from Mount Greylock to North Adams - 6 miles 6 miles / 10 km Day 5 Explore & Day Hike in Williamstown; optional visit to Clark Art Institute - 3 miles 3 miles / 5 km Day 6 Onward Travel

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