The Best Hiking Trails In The Berkshires

The Berkshires are full of good walking, and the best part is the range. You can climb to a rocky summit with hundred-mile views in the morning and roll along a flat, paved rail trail with the family in the afternoon, all within a short drive of Lenox.

Here's how we rank the best hiking trails in the Berkshires for our guests, starting with the one that's practically on our doorstep, only about five minutes away. Whatever your energy and the ages in your group, there's a good match below.

Mahanna Cobble

Best for: a big summit view close to the inn.

Mahanna Cobble is our top pick, and the closest, sitting about a five-minute drive from The Yankee Inn. It's a 222-acre reserve owned by the Berkshire Natural Resources Council (BNRC), and it climbs to the northern summit of Lenox Mountain, a 'cobble' being a Berkshire term for a knob of exposed bedrock high on a ridge.

The trail starts from the Bousquet ski area, which it shares parking with, crosses the base of the ski slopes, then ducks into woodland on a beautifully built path with switchbacks and stone steps. It's roughly a 3.2-mile out-and-back, a steady and moderately challenging climb. At the top, grassy ledges and a stone bench dedicated to BNRC's founding director George Wislocki open to long views south over Kennedy Park and Yokun Ridge. It's free, open dawn to dusk, and a wonderful picnic spot, and dogs are welcome under your control on BNRC and Bousquet land.

Mount Greylock

Best for: the highest, most iconic summit in the state.

Mount Greylock is the tallest peak in Massachusetts at 3,491 feet, topped by the Veterans War Memorial Tower and historic Bascom Lodge. What makes it flexible is that the summit is reachable by car on a seasonal parkway (roughly late May through November 1), so you can hike as much or as little as you like.

The state's suggested day hikes run from easy to aggressive. For an easier outing, the Stony Ledge walk (about 3.8 miles along a dirt road) leads to one of the most dramatic vistas in the park; for a full summit push from the base, the Cheshire Harbor Trail is the shortest, most direct route (about 6.6 miles round trip, moderate to strenuous). A year-round Visitor Center in Lanesborough has maps and water. Wear sturdy boots, start early, keep dogs on a ten-foot leash, and check the state's day-hike guide before you go. It's about a 35-minute drive from the inn.

Monument Mountain

Best for: a rewarding summit with real literary history.

Monument Mountain in Great Barrington is one of the most beloved hikes in the county, a Trustees of Reservations property where more than 20,000 people a year climb to Peeskawso Peak (1,642 feet) for sweeping views over the Housatonic River Valley toward Greylock and the Catskills.

Three trails, all under three miles, let you tailor the effort: the gentler 1.5-mile Mohican Monument Trail, the steeper and more direct 0.83-mile Hickey Trail, and the short Peeskawso Peak connector that carries the best views. A popular loop goes up the gentle side and down the steep one, roughly two and a half to three miles. It's also a literary landmark: Hawthorne and Melville spent a famous afternoon here in 1850 that fed into Moby-Dick. It's open sunrise to sunset; parking is free for Trustees members and $10 for nonmembers, dogs must be leashed, and it's worth taking care on the summit ledges. About a 30-minute drive from Lenox.

Ashuwillticook Rail Trail

Best for: easy, flat family walking and biking.

If you'd rather roll than climb, the Ashuwillticook Rail Trail is the one to pick, especially with kids or bikes. It’s a paved, mostly flat path built on a former rail line, running roughly 15 miles from Adams through Cheshire and Lanesborough into Pittsfield, hugging Cheshire Reservoir and the Hoosic River with Mount Greylock rising in the background.

Because it's level and paved, it suits every ability: walkers, casual cyclists, runners, families with strollers, and cross-country skiers in winter. There are several parking areas and restrooms along the way, plus benches and picnic tables. Rent bikes locally and make a morning of the scenic reservoir stretch. The nearest trailhead, in Lanesborough, is about a 20-minute drive from The Yankee Inn.

A few more trails worth knowing

Kennedy Park is right here in Lenox, minutes from the inn with no drive required. Its smooth, walkable woodland trails and old carriage roads are perfect for an easy stroll or a trail run, and it connects into the wider Lenox trail network. Also in Lenox, Pleasant Valley Wildlife Sanctuary offers seven miles of Mass Audubon trails, from a flat boardwalk loop to a real climb up Lenox Mountain, plus resident beavers.

For a hike with a story, the Keystone Arch Bridges Trail in Chester leads about five miles round trip through the woods to dry-laid stone railroad bridges from the 1840s over the Westfield River; there are no guardrails, so keep children and dogs close. And down in Great Barrington, the Housatonic Rail Trail is a short, accessible, shaded crushed-stone path along the Williams River, ideal for a quiet walk or leaf-peeping in the fall.

When to go and what to bring

Late September through late October is peak foliage and the most popular time to be on the trails, but every season has its draw: spring wildflowers and birdsong, cool summer mornings before the heat, and quiet winter outings, whether snowshoeing up Mahanna Cobble or cross-country skiing the flat rail trails.

Wherever you go, bring water, sturdy boots, and layers, and check the forecast. On rocky summits like Monument Mountain and on the Keystone Arch Bridges, watch your footing near the drop-offs. If you're combining trails over a few days, mix a flat rail trail with one bigger climb, and start early on summer weekends, when the smaller trailhead lots fill up fast.

Berkshires hiking FAQ

What is the best hiking trail near The Yankee Inn?

Mahanna Cobble, a BNRC reserve about five minutes away. Its roughly 3.2-mile out-and-back climbs to the northern summit of Lenox Mountain for long views south over Kennedy Park.

What is the highest peak in the Berkshires?

Mount Greylock, at 3,491 feet, the tallest in Massachusetts. Its summit is reachable by car on a seasonal parkway, so you can hike as much or as little as you like.

Is Monument Mountain a hard hike?

It is manageable for most people with a basic level of fitness. Three trails under three miles let you choose your effort, and a common loop up the gentle Mohican Monument Trail and down the steeper Hickey Trail runs about 2.5 to 3 miles.

Which Berkshires trail is best for kids or biking?

The Ashuwillticook Rail Trail is flat, paved, and family-friendly for walking or biking. Kennedy Park in Lenox is also a gentle, easy option right in town.

Are dogs allowed on these trails?

Generally yes, under control or on a leash: Mahanna Cobble (BNRC land), Mount Greylock (ten-foot leash), and Monument Mountain (leashed). Note that dogs are not allowed on the Mass Audubon land at Pleasant Valley.

Want a base for a few days of Berkshires hiking? See our rooms, with Mahanna Cobble and Kennedy Park just minutes from the inn.