Massachusetts only carries about 90 miles of the Appalachian Trail, but through the Berkshires it packs in some of the most memorable moments a thru-hiker can have: pond-side cabins, volunteer caretakers, roadside trail magic and one very good ice cream shop.
One hiker's account of the stretch makes the case nicely. Pushing a personal-best 27-mile day over three ridges — motivated partly by a wedding back in Philadelphia and partly by the promise of sleeping at Upper Goose Pond — she got a proper taste of what the state does well. Early in the day came trail magic from two local Berkshires hiking groups, complete with cucumber lemonade. Later, a trail stand stocked with chocolate milk, wetland boardwalks, and finally the cabin itself: a volunteer-run spot on a dock-worthy pond that famously serves pancake breakfasts to overnight guests.
The Berkshires also deliver small-town charm right off trail. When her replacement shoes caused painful problems for her high arches, a call ahead to Nature's Closet in Williamstown solved it — staff even offered to pick her up. The college town of Williamstown won her over in under an hour, from its campus to a scoop at Lickety Split, which she recommends to anyone "dairy blazing" the trail. Near the base of Mount Greylock, the communities of North Adams and Williamstown maintain info boards with shuttle drivers and restaurant tips, and hikers report being looked after well.
Logistics matter here too. The caretakers at Upper Goose Pond, locals from central Massachusetts, saved her from a missed train by steering her toward Springfield instead of Holyoke. Mount Greylock, the state's high point, offers a tower and views at the top, and from there it's a short push to the Vermont border.
For holidaymakers rather than thru-hikers, the takeaway is that the Berkshires work as a soft entry into long-distance hiking. Day hikes around Upper Goose Pond or Mount Greylock give you the scenery — farmland views, low rolling fog, quiet forest — without committing to 2,000 miles. Williamstown makes a pleasant base with its college-town eating and café scene, and the trail infrastructure (shuttles, hiker boxes, gear shops like Nature's Closet) means help is never far away. If you're section-hiking, note the local wisdom: flat states are smarter for big-mile days, so keep Berkshire plans modest and savour the towns.
The writer passed through in summer, when camp kids were out on day hikes and the grass was tick-friendly — worth remembering if you're planning a warm-weather trip. Fall, when the Berkshires' foliage is legendary, is the classic alternative.
Story via The Trek.
