Travel Guide to West Stockbridge and Its 7 Best Attractions

Surrounded by forests, valleys, and the billowy green mountains of the Berkshires, West Stockbridge is one of those little towns you could miss in a blink on a bike ride to Tanglewood. It gets lost in the stretches of highway between American cultural epicenters of Boston and New York; its geographic borders muddled in the sweeping New England greenery and farmhouse landscape. However, visitors passing through would be remiss not to spend a few hours in West Stockbridge. The locals are friendly, the winding nature paths resplendent, and the local businesses unique and welcoming. For a reclusive weekend or day alone in the woods, West Stockbridge has got you sorted.

Photo by seagully/Flickr.

Take a hike at one of West Stockbridge’s many area hiking trails

When in the Berkshires – hike! Every season has its charms up in the tree-peppered mountains. And, of course, there are so many mountains and so many trees. Hit Bartholomew’s Cobble, a hundred-foot-high bedrock outcropping rising to elevations of a thousand feet, and featuring over 800 varieties of plants and sweeping views of the mountain vistas, or head 16 miles out of West Stockbridge to check out Bash Bish Falls, Massachusetts’ highest single-drop waterfall. When surrounded by all this nature, it would simply be a waste to not explore it.

Cyclists will love pedalling through the New England landscape

Why hike when you can bike? Trails abound, through the mountains, plains, forests and rolling Berkshire hills. Visitors enjoy the journey just as much as the destination, especially if it’s a fall day and they’re following the trails from North Egremont, through the Taconic Mountains and ending up at the Norman Rockwell Museum. Pass farmhouses, highways and roads, rivers, forest clearings and cut through the passages of the great American landscape on two wheels. Check out the Berkshire Cycle Touring company for a group ride, or take their six-day tour of South Berkshire.

The Shaker Dam Coffeehouse and Stanmeyer Gallery merges caffeine and culture and excels at both

This is a seriously cool little coffeehouse. Apart from being total, unabashed, unashamed and fiercely passionate coffee-nerds, the owners of Shaker Dam and Stanmeyer Gallery are, respectively, a National Geographic photographer, author and educator, and his wife, the editor of the Berkshire Magazine. They are both enviably well traveled, and both have bylines in publications like Time, Newsweek and more. And they have a coffee shop that prides itself on its locally sourced, sustainable beans and the innovative Modbar Espresso System to pump out shot after shot of smooth, artistically pulled espresso. A café downstairs and gallery and workshop space upstairs, the owners have definitely struck that delicate balance of caffeine and culture.

Grab a few plates of tapas or a good old American burger at Rouge, a local favorite

Photo via their official site.

This French-flavored bistro is a local classic. They offer a burger that more than a few West Stockbridge inhabitants hail as the best burger in town, topped with fontina, tomato and field greens, and the restaurant itself is cozy and comforting, with vibrant reds and yellows on the walls, patches of exposed brick wall all neatly gussied up with Christmas lights. The executive chef and owner has lived in three Pyrénées cities, so his culinary creations are always influenced to some degree by French or Spanish cuisine, whether it’s the brochette of escargot or chorizo tapas. Go for a cocktail and small sharing plates or a full-out three course French meal – Rouge is all-accommodating.

Spend a night at the Shaker Mill Inn

The Shaker Mill Inn is a classic New England bed and breakfast nestled in a secluded wooded area just three miles from Tanglewood, and just as close to other area attractions like the Norman Rockwell Museum, Chesterwood and certain Gilded Age mansions. Surrounded by forest hiking trails, state parks and ski hills, the Shaker Mill is just the place to remind travelers that the best way to explore nature is to live in it.