Slackpacking Massachusetts

Destination: Stockbridge, Massachusetts

| Activities: Hiking and Slackpacking

The Appalachian Trail truly has mythic status and for many of us, hiking it is a dream. But then we look at the reality of it and find the prospect of carrying a 40-50 pound pack on our back and sleeping on the ground rather daunting. Solution? Slackpacking! We cover the same distance as backpackers, but at the end of the day we return to a comfortable lodging with beds and hot showers. This section of the AT has a wide variety of terrain, with roots, rocks, steep climbs and incredible views. We end the trip by summiting Mt. Greylock, the highest mountain in Massachusetts. Maximum group size: 10


  • Hiking the highest point in Massachusetts - Mount Greylock at 3,487 feet
  • Returning to a comfortable bed and hot shower at the end of every day
  • Exploring the expansive highlands of the Berkshire region of Massachusetts
  • Carrying only what you need for the day on your back

Departures and Prices

June 18 to June 25, 2023
$2895.00 - FULL
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June 26 to July 03, 2023
$2895.00 - Available
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  • 2-3 experienced AGC guides based on group size
  • Seven nights lodging
  • All meals from dinner on the first day through breakfast on the last day
  • All transportation within Massachusetts including round trip transport between the Albany International Airport our vacation home in Stockbridge, MA and daily shuttles to and from trailheads
  • Park entry fees
  • Not included: Transportation to Albany, alcoholic beverages, guide gratuities, and travel insurance.

Trip Documents

Trip Info

Hiking from 8 to 15 miles a day (see the itinerary for daily mileage) with one 3,000-foot ascent, particularly on a trail with many rocks, roots, and muddy sections - even if the terrain is flatter than most sections of the AT - requires being in excellent physical condition and prior hiking experience. If you need a down day, you can always choose to stay at the rental house and explore the town. This trip is rated 5 and requires a high degree of fitness. Adding some specific conditioning such as strength training, endurance training, and longer aerobic workouts is suggested. Rating: 1 2 3 4 [5]

This is a challenging hiking trip on the Appalachian Trail. The Appalachian Trail travels 90 miles in Massachusetts. While some of the hiking is relatively well-graded, hikers should be ready to encounter rough and rocky trails, some steep climbs and descents, and some long ascents and descents. Depending on weather, hikers may encounter muddy trails and rocks and roots that will be slippery when wet. In Massachusetts, the Appalachian Trail crosses over hills and valleys and through several towns in the Berkshires. Hikers should be comfortable hiking up to 15 miles a day for multiple days in a row.

We will be staying at a beautiful, historic home in Stockbridge, MA. This trip is unique in that every single participant gets her own room and we have the entire home to ourselves! The home sits by the edge of a field with garden and blackberry patch and is surrounded by 25 acres of woods. Walking paths on the property Villa Favorita was built in 1918, upgraded to its current structure soon after by Clive Livingston Duval I (father of a Virginia Senator of the same name), and later became the home of royalty, Prince and Princess Sapieha, after they escaped Eastern Europe during WWII. Former residents kept their own horses here, and former pasture, equestrian fields and orchards have now evolved into wild meadows, cultivated blackberry and raspberry fields, and pathways through forests of pine, maple and fruit trees.

Below is the proposed itinerary for the trip. As is true on any adventure travel trip, plans for any specific day may be modified due to weather considerations, unforeseen circumstances, new opportunities, and group interests.

There are approximately 90 miles of the Appalachian Trail in Massachusetts and we will slackpack the most beautiful section, starting close to the border with Connecticut and ending on the summit of Mount Greylock, the highest point in the state! Plan to fly into the Albany Airport (ALB) by 1:30PM for our 2PM group meeting. We will drive one hour east to our beautiful Victorian rental house in Stockbridge, Massachusetts. This small town is home to big charms like the Norman Rockwell Museum and Tanglewood, the Boston symphony orchestra's summer academy. Time to relax and spread out, on this slackpacking adventure everyone gets her own private room! Tonight we'll get to know each other over the first of many delicious meals. (D)

Overnight: Stockbridge, MA
We'll start the week by hiking close to our lodging with lower miles and shorter transports, warming up to longer and farther away pursuits on the AT. Today's 8 mile jaunt has a bit of everything: ups, downs, dense forest, sweeping views, rocks - you name it! The Berkshires have been described as a 'mosaic of wetlands and forests,' and this verdant green scene was once home to the now extinct Catamount or Eastern cougar. These days we are more likely to see red and gray foxes, wild turkey, opossums, deer and woodchucks. (B, L, D)

Distance: 8 miles

Total Elevation Gain: 1,732 feet Total Elevation Loss: 1,411 feet

Overnight: Stockbridge, MA

Each day we'll start where we left off the afternoon before, linking together a long section of the AT. One of the best aspects of hiking the Appalachian Trail in Massachusetts is the many points of egress at road crossings. We'll feel like we are alternately in the middle of nowhere and strolling through "America's backyard" - truly an AT experience! While we are intentionally ramping up the mileage to the middle of the trip and then decreasing it again, we know that not everything goes according to plan all the time. Fortunately, if a hiker gets a blister, it's an easy exit from the trail back to the house each day. (B, L, D) Distance: 12.2 miles

Total Elevation Gain: 2,415 feet Total Elevation Loss: 2,510 feet

Overnight: Stockbridge, MA

June is an excellent time to hike on this part of the AT, not too cold and not too hot with lots of blooming wildflowers. If we're lucky we'll see Magnolias, Echinacea, Poppies, Black Eyed Susans, Butterfly Milkweed, and White Wild Indigo among others. If we can muster the energy tonight, it may be a great time to schedule a massage at the inn down the street from our lodging! Distance: 13.8 miles

Total Elevation Gain: 3,120 feet Total Elevation Loss: 2,228 feet

Overnight: Stockbridge, MA

Hike, eat, sleep, repeat. The only thing we have to worry about is putting one foot in front of the other and enjoying the view. Our hike today lands us in the town of Dalton, which is an officially recognized "Appalachian Trail Community". There are 51 towns along the AT that have received this recognition from the Appalachian Trail Conservancy. We can head out on the town tonight knowing that as AT hikers we are especially welcome and supported here. We'll celebrate our longest hiking day yet with a delectable dinner out! (B, L, D)

Distance: 14 miles

Total Elevation Gain: 1,703 feet Total Elevation Loss: 2,395 feet

Overnight: Stockbridge, MA
Today we start to decrease the mileage in anticipation of our summit day tomorrow on Greylock! Keep an eye out for Spotted Newts as you traipse through fern groves along today's moderately challenging route. We'll pass by bubbling streams, a perfect picnic pond, and enjoy the beautiful view from the Cheshire Cobbles on this peaceful penultimate hike. (B, L, D)

Distance: 9.2 miles

Total Elevation Gain: 1,512 feet Total Elevation Loss: 1,708 feet

Overnight: Stockbridge, MA

Did you know that Herman Melville was living in his Berkshires home when he penned Moby Dick? Many think that his famous white whale was inspired by Mt. Greylock. Unlike Captain Ahab though, we have no revenge to seek and can hike joyfully to the top of this beautiful mountain! If the day is clear, at the summit we'll be rewarded with a 90 mile vistas of 4 different states and 5 mountain ranges, "a monarch among its fellows." Towering over the Hoosac valley, Mt Greylock stands at 3,491 feet and is the highest peak in Massachusetts. It also comprises Massachusetts' only subalpine environment and is the only significant boreal forest in southern New England. Wow! Tonight we celebrate our accomplishments with our final group dinner. (B, L, D)

Distance: 8.1 miles

Total Elevation Gain: 2,986 feet Total Elevation Loss: 492 feet

Overnight: Stockbridge, MA
We did it - we hiked nearly all of the Appalachian Trail in Massachusetts! If you drove, you can leave at any time today. If you flew, we'll have you back to the Albany airport in time for flights departing out after 1PM. (B)

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  1. Where do we eat?

    The guides will be cooking breakfasts and most dinners at the vacation home. Before you leave in the morning the guides will put out lunch options and you will prepare a packed lunch. You'll go out for one dinner where you can order off the menu; other nights you'll relax in the vacation home and have dinner there.
  2. What dietary preferences or restrictions can you accommodate on this trip?

    If we know well in advance, we can accommodate vegetarian, lactose-free, and gluten-sensitive diets. We cannot guarantee a completely gluten-free diet and we cannot provide a kitchen guaranteed to be free of cross-contamination. If you are vegan, we ask that you bring some additional protein bars; and if you are gluten-sensitive, please bring some gluten-free snacks. If you have severe allergies, Celiac disease and/or other significant dietary restrictions, please call the office before you register.