Appalachian Trail: Hiking the Berkshires

7 Days & 6 Nights 4.4 Read 8 reviews
  • Hike part of the 2,185-mile Appalachian Trail stretching from Georgia to Maine
  • Overnight in comfort, at a mix of hand-picked hotels and a B&B
  • 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’
Hike a section of the stunnng 2,185 mile Appalachian Trail with opportunities to explore classic New England towns. Explore the Berkshires on two feet – to find the gems hidden in the “Purple Valley.” Try out local flavors in Lenox, one of the Berkshire's cultural centers. 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 a walk up to the summit of Mount Greylock, the highest peak in Massachusetts. Culminate your adventure with a day in charismatic Williamstown, offering the Clark Institute with its fantastic art collection with works from artists such as Renoir, Van Gogh and Homer, or admire this town's architecture and visit the boutique shops and restaurants and enjoy it's small-town friendliness.
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. You will need however to be a seasoned hiker with experience of long-distance trail walking. This moderate trip has great walks which are followed by overnights in charming inns and hotels. Try this tour for a taste of AT culture, camaraderie, and beauty, without forgetting that you’re on vacation!

Tour Type:

Classic Routes | If you’re the active, outdoorsy type, who’s interested in taking on the great routes of the world or looking for a challenge, then our Classic Routes are for you. We’re talking the West Highland Way, Tour Du Mont Blanc and the Passau to Vienna Danube Cycle Path, to name but a few!


Inn to Inn Walking | Walk from place-to-place changing accommodations each night. Generally staying in B&B’s, inns, and guesthouses.

This trip is suitable for:

Solo Travellers

As a guide, we would suggest that the minimum age of traveler this tour would be suitable for is: 12 Years

Ideal if you have an interest in:

  • Long-Distance Trails
  • Off the Beaten Track

Activity Level & Terrain

The hiking on this trip is moderate. The trails on the Appalachian Trail iself are most challenging and particularly your walk on Day 4 up to Mount Greylock with a long ascent and little respite. However you have all day to do it. The following day involves very little ascent and the distance is shorter. The loop walks, both in Lenox and Williamstown are a lot less challenging and involve some sidewalks, paved roads, and dirt single tracks.


Navigating is easy using the Macs Adventure Smartphone App. Your daily walks 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 itself 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 having to navigate rocks, and tree roots. During heavy rains it may get very muddy. You should be accustomed to hiking for several hours at a time and will enjoy your tour much more if you are well-prepared. Long-distance hiking experience is definitely 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 six nights in comfortable accommodations, including classic New England hotels, B&B's and a Scandanavian-style lodging specifically created for walkers. You will recieive a good 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.


We will try to book accommodations where breakfasts are included. However we may need to use accommodations which do not provide breakfast. If this is the case we will provide a discount for those mornings when it is not included. When it is not included there will be plenty of places where you may find cafe's where you may purchase it yourself.

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.

Dinners are not included; when in Lenox and Williamstown, you will have many excellent restaurants to choose from. On your overnights 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. For further details and pricing, please ask us at the time of booking.

  • 6 nights in classic New England hotels and a B&B
  • 6 Breakfasts (wherever possible)
  • Transfers to and from trailheads as listed in the itinerary
  • 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/North Adams
  • Lunches & Dinners
  • Breakfasts (if the hotel cannot provide it)
  • Personal equipment
  • Travel Insurance
  • Additional nights before, during, or after your trip
  • Airport transfers (if desired)

When To Go

This tour operates anytime from the beginning of June through to October. There are reasons to go to the Berkshires in each season based on your goals. In 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. This trip cannot be taken in May due to the fact that there may still be snow on the trails.

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 first week in June through to 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. 

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 (1H) and Bradley International Airport(1H15). We would be happy to arrange a private transfer from either directly to your hotel. However this request needs to be made as far in advance of your trip as possible. If last-minute requests are made it's possible that our transfer provider will already be fully booked. 

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 (4H), 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 from Lenox). 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). As Lenox is a small town it's also possible to find on street parking, although not in the town centre. Driving times are as follows: Albany, NY - 1H; Hartford, CT - 1H15; Boston, MA - 3H; New York City, NY - 3H30.  

Getting from the End

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

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. However these requests need to be made as far in advance as possible. Last minute requests cannot always be honoured. 

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).

General Information

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.

What happens if I can’t walk a stage?
How far in advance do I need to book?
What personal equipment do I need?


Day 1 Arrive Lenox and overnight Day 2 A warm-up loop walk in Kennedy Park 5 miles / 8 km Day 3 Appalachian Trail from Dalton to Cheshire 9 miles / 14 km Day 4 Appalachian Trail from Cheshire to Mount Greylock - 8 miles 8 miles / 13 km Day 5 Appalachian Trail from Mount Greylock to North Adams - 6 miles 6 miles / 10 km Day 6 Explore & Day Hike in Williamstown; optional visit to Clark Art Institute 3 miles / 5 km Day 7 Onward Travel

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