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5 Berkshire hikes with great views

The Berkshires has no shortage of beautiful hikes. If you’re looking for a good view and up for a bit of a climb, here are a few with spectacular views.

sunset at Spruce Hill

The view from Spruce Hill at sunset.

Spruce Hill

North Adams

A roughly 6-mile round trip hike to Spruce Hill offers views of Mount Greylock, Adams and North Adams. You can access the trail and parking from Route 2, about a mile from the Hairpin Turn driving eastbound (just after the Wigwam and Western Summit cabins). The Hoosac Tunnel runs through the mountain range.

Less than a mile into the hike, you’ll also find a scenic view at Sunset Rock. If you go for a sunset hike, just remember to bring a headlamp or flashlight in case you are hiking back in the dark. The trail is uphill at first, and then later levels off as you walk along a ridge. A trail map can be found on the Berkshire Natural Resources Council website, bnrc.org.

pine cobble lookout

The view at the top of Pine Cobble.

Pine Cobble


Though it is only about a 1.5-mile hike to the summit, the climb is steadily uphill on the Pine Cobble Trail. Parking can be found down Pine Cobble Road not far from its intersection with North Hoosac Road, and the trail starts on the east side of the road. A map can be found on Williamstown Rural Land’s website, rurallands.org.

cheshire cobble

A view from Cheshire Cobble.

Cheshire Cobbles


Follow the Appalachian Trail at the end of Furnace Hill Road in Cheshire about a mile to a vista. From the top, you can see the Cheshire Reservoir and Mount Greylock in the distance. You also might meet an Appalachian Trail “thru-hiker,” someone who is trekking the more than 2,000 miles from Georgia to Maine. A good place to park for the hike is at the Ashuwillticook Rail Trail parking on Railroad Street, which is about a half-mile from the trailhead.

flag rock

The view from Flag Rock.

Flag Rock

Great Barrington

This 3.6 miles round trip hike on the Monument Mountain reservation. The mountain was a sacred site for the Mohican people before they were driven out of their homelands. Flag Rock, an overlook at about 1,400 feet, offers views of the village of Housatonic in Great Barrington. And, as the name suggests, there is an American flag at the top. Parking is off Route 183 where Willow’s Trail, marked in orange, starts. Want a longer hike and another view? You can add in Peeskawso Peak by taking the Cross Over Trail to the Mohican Monument Trail onto the Peeskawso Peak Trail. A detailed map of Monument Mountain can be found on The Trustees of Reservations website, thetrustees.org.


A view from near the top of Greylock.

Mount Greylock


At 3,491 feet, Mount Greylock towers over Massachusetts as the highest point in the commonwealth and boasts views of 90 miles away on a clear day. There are a few ways to hike to the top, including taking the Cheshire Harbor Trail, which starts at the end of West Mountain Road in Adams, or Bellow’s Pipe, which starts off of Gould Road in Adams. Hiking either of those trails is about a 6-mile round trip. A detailed map can be found on the state Department of Conservation and Recreation’s website. At the grassy, park-like mountaintop, you’ll find Bascom Lodge and the 90-foot tall Veterans War Memorial Tower, which you can climb a spiral staircase to the top, in case the hike to the peak wasn’t enough for you. This is also an accessible view — you can drive up the mountain.

Greta Jochem can be reached at gjochem@berkshireeagle.com or 413-496-6272.


Greta Jochem, a Report for America Corps member, joined the Eagle in 2021. Previously, she was a reporter at the Daily Hampshire Gazette. She is also a member of the investigations team.

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