Drive out Route 2 to Mount Greylock and North Adams, with some mill towns in-between.
Western Massachusetts and the Berkshires are an easy trek from the coast. Head out across the state on MA Route 2 and you'll find many great stops along the way. We love Honest Weight Brewery in Orange, and another great stop is Brick and Feather Brewery in Turners Falls, just after the French King Bridge crosses the Connecticut River. Sample all of their beers in small pours and then go for a walk around the old town along the Connecticut River. The Canalside Rail Trail is a 4 mile path the starts in Turners Falls, and goes over the Connecticut River into Deerfield.
This drive along Route 2 will give you such a great glimpse of Massachusetts history. The towns banking Route 2, especially along the Mohawk Trail, were so intertwined with the industrial revolution spawning from the Blackstone River Valley. These towns still show evidence of the textile mills that put them on the map in the 19th century. Orange, Turners Falls, Greenfield, and of course our final destination of North Adams have some interesting repurposed spaces to explore, along with some great peaks and ledges to climb.
Poet's Seat Tower sits on the edge of a cliff at the highest point in the town of Greenfield. A wooden tower was built in 1879 but after a fire was replaced by the current stone tower in 1912. From the parking area you can pick up the Greenfield Ridge / Rocky Mountain Park Loop towards the tower. This trail also connects to the White Diamond and Red Blaze trails which take you down closer to the Connecticut River.
After exploring these old industrial towns, head further west to North Adams, the coolest mill town on the Hoosic River. It's worth staying here for a few days. Off-season is quiet, with many accomodation options, plus the town is beautiful in the snow. Walk around the Church Street–Cady Hill Historic District, and then through the neighborhoods to find some stick style and Queen Anne architecture.
Natural Bridge State Park, just east of downtown North Adams, is home to a natural white marble arch, and a man-made white marble dam. There's a half-mile walk above and through the bridge, and a few more trails to explore around the park.
Once we were settled in the town, had walked around and had a few good meals, we planned to spend a whole day hiking Mount Greylock. If you're willing to walk an extra few miles, you can actually hit some trail heads by starting right in downtown North Adams. We walked through town and then down Reservoir Road to Bellows Pipe Trail. From there, you'll hit the Thunderbolt Trail, which zigzags like a thunderbolt up to the Appalachian Trail, and finally to the summit of Greylock. From the center of North Adams to the summit of Greylock, and back down to the center of town, the hike was about a 16 miles long.
Back in town, head to MASS MoCA for an afternoon. This museum is an amazing space to explore. The old mill buildings that are its galleries are as beautiful to look at as the exhibitions. Grab a beer at the brewery in the museum called Bright Ideas Brewing, or at the adjacent Mohawk Tavern.
The Sterling and Francine Clark Art Institute, or Clark Art, is a few more miles west on Route 2 from North Adams, in neighboring Williamstown. The museum has an amazing collection of French Impressionism, and excellent American collections including works by Winslow Homer and Frederic Remington. After your museum visit, check out the walking trails all along the property. Walk the trail up historic Stone Hill for views of Williamstown and the Green Mountains of Vermont.
End the weekend by traveling south to Becket, for a drink at the Dream-Away LodgE. This place is a legendary bustling farmhouse with a local menu and live music. The atmosphere is sweet and eclectic. The expansive grounds are beautiful, with a fire pit and gardens. You won't want to leave.
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