The Berkshires Blog

Leaf Peeping Is Not Canceled: 6 Drives and Hikes to Try This Fall

“Fall is far and away my favorite time in the Berkshires”

Written by Mark Vanhoenacker
October, 2020

Massachusetts, The Berkshires

The first frosty nights (farewell, mosquitoes); T-shirt days under Windex-hued skies; a nearly unbroken tapestry of the foliage that inspired Herman Melville to write that “sunrises and sunsets grow side by side in these woods”; and warm bags of the cider-infused doughnuts that are every hiker’s reward: Fall is far and away my favorite time in the Berkshires

This autumn, the region offers opportunities to alternate new trails with old favorites. But first, a few planning tips. I recommend the BNRC Berkshire Trails app from the Berkshire Natural Resources Council. You could spend a wonderful week wandering Berkshire County’s back roads, using this app to guide you from one secluded wonder to the next. Note, too, that many leading cultural venues — including the Clark Art Institute, Hancock Shaker Village and The Mount, Edith Wharton’s former home — are not only open, but are surrounded by paths and gentle trails on which it’s easy to socially distance, and to sidestep, too, that tough Berkshires call: culture or nature?

Most important, check Massachusetts’s strict quarantine rules before you leave home. Oh, and dress brightly — it’s hunting season. And watch out for bears.

Start your day at Dottie’s Coffee Lounge in Pittsfield, my hometown, where Jess Lamb (who previously practiced her craft at Joe Coffee on East 13th Street in Manhattan) and her colleagues create the county’s richest-tasting lattes with beans from Barrington Coffee and milk from High Lawn Farm, both in nearby Lee. Then drive west to Pittsfield State Forest (free).

Around 30 miles of trails lace this roughly 11,000-acre realm, which once formed part of Mohican and Mohawk hunting grounds. Later, the Shakers settled here. Their graves, former settlements and dancing sites still can still be found among the stands of sugar maple, oak, birch and white pine.

First-time visitors should head to Berry Pond. At around 2,150 feet, it’s the state’s highest natural body of water. My mother and I often came here to pick blueberries, so imagine my surprise when I learned that it was named for William Berry, a Revolutionary War hero.

A network of steepish trails or a scenic one-way loop road, built by the New Deal-era Civilian Conservation Corps, can take you up (the road is curvy and narrow; pedestrians, cyclists and motorists should keep a close eye out for one another). Enjoy the spectacular westerly overlook (hello, to paraphrase the McGarrigle sisters, to the state of old New York!). Then head downhill to the pond for a view of the season’s colors, pleasingly doubled by the water’s mirror.

The world’s most mouthwatering cider doughnuts still come from Bartlett’s Orchard in Richmond. So busy was their farm shop this summer that they’ve instituted weekend online ordering and curbside pickup for the fall; you can still pick apples in the orchards behind the shop. From here, drive or cycle to Parsons Marsh, a B.N.R.C. property in Lenox that opened in 2018. A trail and boardwalk (free; one-third of a mile each way; wheelchair accessible) wind through a woodland worthy of Tolkien’s Galadriel, and wetlands even now bursting with life. Along the marsh’s edge you’ll find haunting examples of the still-standing dead trees known as snags — fine lookouts for raptors — and your own tranquil views (see the beaver lodge?) from the deck at the boardwalk’s end.

Then head to Bousquet Mountain, site of my first childhood ski lessons on Drifter, a gentle slope that’s now also the start of the three-season Mahanna Cobble Trail (free; 1.4 miles each way; elevation gain, around 750 feet). Mahanna Cobble opened in June. It’s the newest stretch of the B.N.R.C.’s High Road initiative, a long-term plan, inspired in part by the Camino de Santiago pilgrimage route through Spain, to use both old and recently cut trails to reconnect Berkshire landscapes and communities.

Along the trail’s first few hundred yards I was surprised to find myself ascending, for the first time, a ski slope I once knew well. But under the shimmering dragonflies and a still-warm September sun, the slope I long ago slid down seemed only a steep meadow, overgrown with late-season blooms of chicory and white wood aster. Soon the trail leaves the ski run — and memories of cooler kids racing past me like Oz’s winged monkeys — behind and climbs into a forest of oak, hickory, birch and beech. When you’re out of breath, take heart, and perhaps a photograph: Temperature generally falls with elevation, so the more vertical your hike, the more likely you are to find yourself surrounded by foliage at its peak of color.

A view is the more obvious gift of altitude. You’ll soon reach a south-facing overlook above a steep clearing. It’s a good spot to count how few doughnuts remain, and to console yourself with as fine a perspective as any on Monument Mountain, not far at all as the hawks above you might fly.

This overlook marks the end of the Mahanna Cobble Trail, but it’s only the beginning of other paths that lead away along the ridge and the High Road you’ve already started down. Go far enough and you’ll reach my mom’s memorial bench — “who loved these hills,” reads the inscription my brother and I chose — where she’d be as happy as I always am to find a traveler at rest.

For more great Leaf Peeping, click here.