Self Guided Walking Holidays & Cycling Holidays

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Self-Guided inn-to-inn hiking on the Appalachian Trail


  • 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.

Day 1: Arrive Lenox

The small, classic New England town is the perfect jumping-off point for this tour. It is home to beautiful rolling hills, world class restaurants, the Boston Symphony Orchestra's Tanglewood, and countless cultural activities. A favorite for locals and visitors alike, the quaint setting will make you want to stay forever.

Overnight: Lenox

Day 2: Hike Appalachian Trail from Dalton to Cheshire

A 25-minute transfer will deposit you at the southern terminus of your Appalachian Trail section hike, just north of the community of Dalton. From here, you’ll ascend steadily, so enjoy the warm-up and take in your surroundings. Enveloping the trail are mixed hardwood and hemlock forests, carpeted with wildflowers in spring and later mushrooms, berries, and a verdant understory. Today you’ll pass Gore Pond and later Cheshire Cobbles, a quartzite outcropping with sweeping views of the trail ahead, including the town of Cheshire, Hoosic Lake, and the Greylock massif.

Hike: 8 mi +1080/-1280 ft

Overnight: Cheshire

Day 3: Hike Appalachian Trail from Cheshire to Mount Greylock

Prepare for a climb today by fueling up on a hearty homemade breakfast before departing. The white blazes (marking the entire Appalachian Trail) brazenly invite you to continue northward, despite an unrelenting grade. Take your time, and keep a lookout for wildlife, including black bears, white-tailed deer, red fox, and porcupines.

Once you’ve attained the ridge, about five miles into your hike, the grade lets up as you traverse to the summit of Mount Greylock, the highest point in Massachusetts at 3,492 feet. Take pride in the accomplishment of summitting under your own power, then explore the attractive meadow, the 93-foot lighthouse-like war memorial, and the charming lodge built from local stone and red spruce. Views into five states can be had on a clear day!

Hike: 8 mi +2720/-230 ft

Dinner & Overnight: Bascom Lodge, Mount Greylock

Day 4: Hike Appalachian Trail from Mount Greylock to North Adams

Fitting after your long climb yesterday, the route today is mostly descending from the State’s climactic peak to the idyllic villages below. After a morning of walking, you’ll begin to see signs of civilization, and take a short transfer to Williamstown.

If you’re pining for the trail in the future, it will be easy to return to this point and head northbound, but you’ll need your tent and camping gear as the trail immediately enters Vermont, a signal to AT thru-hikers (those finishing the entire trail in a season!) that the most difficult miles lie between them and Mount Katahdin, the trail’s northern extremity.

Officially off the wilderness trail and back in a modern vacation mecca, treat yourself to a cold New England IPA - the region’s signature craft beer, known for its cloudy body and juicy hoppiness.

Hike: 6 mi +370/-3150 ft

Overnight: Williamstown

Day 5: Explore & Day Hike in Williamstown; optional visit to Clark Art Institute

Home to Williams College, a small liberal arts university, the northwestern-most town in the State is also known as ‘The Village Beautiful’ - and rightly so. Grandiose stone buildings and manicured green lawns stretch outwards from the college campus; a street of vibrant shopfronts fills with students, tourists, and locals alike; and the purple and blue silhouettes of the Berkshire and Taconic ranges stand proudly in the background.

Enjoy a leisurely walk from the town’s bustling Spring Street to bucolic Stone Hill, potentially sidestepping black-and-white cows grazing in the pasture there. Opt for an afternoon at the Clark Art Institute (payable locally), browsing an exhibit of early American oil paintings, or choose to circle back to a lively local eatery for a celebration of your adventures. Many visitors flock to Williamstown for its summer theatre, regional art scene, academic prestige, and recreational opportunities, so you won’t be lacking things to do if you’re sticking around for a few days.

Hike: 3 mi +/-246 ft

Overnight: Williamstown

Day 6: Onward Travel

Easily accessed by bus or a one-hour private transfer to the airport, Williamstown may feel like a million miles from home, but it’s easy to make your onward travel plans.



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 Pittsfield. 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.




Hotel on North

Harbour House Inn B&B

Innkeepers Jennifer and David look forward to welcoming guests, especially those on foot, to enjoy their homemade desserts, evening wine and cordials, and hearty hiker-friendly breakfast, the perfect preparation for the trail.







Bascom Lodge

This unique 1930s-built schist and spruce lodge offers simple private rooms (as well as group bunks), a locally-sourced fixed menu dinner, shared bathrooms with hot showers, and an unparalleled view from the roof of Massachusetts.







The House on Main Street B&B

Set back just enough for peace and tranquility, but only a short walk into town, this classic New England B&B will make you feel like you’re visiting family, right down to the friendly cats at breakfast and the personal welcome from Timothy and Donna.







Optional Upgrade - Orchards Hotel

All the amenities of a modern resort packed into a charming Berkshires hotel, the Orchards provides upscale lodging, dining, outdoor terrace, and purple valley views.





This trip is available from the last week in May through to the middle of 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 recommend as there are numerous highlights and lovely optional day walks.

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.


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 & Grade

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.

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.


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.

Getting Around

Transportation from Pittsfield 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.

Baggage 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).

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.

Getting to Lenox

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 Williamstown

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).



  • 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
  • Single room or solo supplement (if required)
  • Airport transfers (if desired)
  • Hotel upgrade in Williamstown

What happens if I can’t walk a stage?

You will find contact information for our local transportation partner in your pre-departure information pack. If you require a lift on one of your walking days, please inquire ahead of time if possible. Fees apply to all additional transport. As always, if issues arise, Macs Adventure is only a phone call away.

How far in advance do I need to book?

We suggest you book as soon as your plans are finalized as this is a popular tourist destination. Please note you can start this tour on any day of the week, but lodging availability is more limited on weekends.

What personal equipment do I need?

You will need good hiking shoes/boots, comfortable walking clothes (non-cotton is advised), waterproof raingear, a daypack, and warm layers. We supply a detailed packing list with your information pack.

Perfect trip


Really good trip which went very smoothly. The final nights accomodation was fine however missed host contact at other locations. We arranged our own transfers to Lenox and back from Williamstown to catch Pittsfield train.




Appalachian Trail: Hiking the Berkshires

5.0 1


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