Full set of photos here
Sheffield
-To describe my recent sojourn in the Berkshires I'll start at the southern end of the region and move north. The reason I went to Sheffield was to see Ashley House, to pay tribute to Elizabeth Freeman who was a house slave there but who in 1791 sued for her freedom and won.
Great Barrington
-If you visit the Berkshires you must stay at the Briarcliff Motel, a vintage motor hotel lovingly converted by proprietors Richard and Clare into a contemporary B&B. Enjoy Clare's scones and Richard's granola for breakfast at the beginning of your day and enjoy stargazing by the fire pit at the end of it.
-Great Barrington also has a few important stops on the Upper Housatonic Valley African American Heritage Trail, including the W.E.B. Du Bois Homesite and also a lovely wee River Garden Park dedicated to the great man.
-My dinner at Prairie Whale: a Salty Fairy cocktail + tagliatelle with kale, shiitake mushrooms, and egg yolk + a side of cornbread + flourless chocolate cake for dessert.
Stockbridge
-Due to a TSA-related travel snafu I missed out on a full day of my vacation and therefore did not make it to Chesterwood or the Roz Chast exhibit at the Norman Rockwell Museum, but I sure did have an idyllic afternoon on the grounds of the Gilded Age "cottage" Naumkeag. The house is a wonder and filled with treasures, but the formal gardens designed by Fletcher Steele are even more magnificent.
-While in Stockbridge also seek out Elizabeth Freeman's grave in the old cemetery, leave a stone.
West Stockbridge
-The No. Six Depot is well worth a stop, situated in the old train station in West Stockbridge, for a meal or cup of coffee or for shopping for local delicacies.
Lee
-Simpsons fans will appreciate Moe's Tavern for obvious reasons, but it's also an excellent place to try a local brew or two or three.
Becket
-Or head up a vaguely treacherous road into the October Mountain State Forest to the magical Dream Away Lodge, where on Wednesday nights musicians take turns singing old-timey tunes and everyone is invited to join in.
Lenox
-If you're in town during the Tanglewood season by all means picnic on the lawn there before a concert, or take an evening ghost tour at The Mount, Edith Wharton's palatial estate where she composed some of her most famous works, or just have dinner at Brava.
-My dinner at Nudel: a Ballast Point Grapefruit Sculpin + strawberries and pea shoots, farro, pecorino, aged balsamic, toasted oats, mint + spaghetti, shaved zucchini, garlic scape, pine nut and green olive pesto, Parmesan + warm crumbled corn bread, rhubarb, strawberries, jalapeno ice cream and toasted corn flakes.
-For an impressive selection of booze to take on your picnic or back to your hotel room check out Spirited.
Richmond
-One of my favorite things in the Berkshires were all of the pint-sized grocery stores/farmstands, each one with its own specialty. At Bartlett's Orchard head straight for the cider doughnuts, do not pass go.
Pittsfield
-Herman Melville made his home here and named it Arrowhead. He loved the house so much he composed a famous ode to its fireplace, "I and My Chimney," and also wrote all of Moby-Dick in a frenzy of creativity in his study on the second floor while gazing towards the whale's-back shape of Mount Greylock.
-If you're craving a real East Coast bagel you can't go wrong at Bagels Too.
-And Pittsfield State Forest has some lovely ponds by which to eat said bagel.
Dalton
-Berkshire Organics is another one of those wee Berkshire groceries, this one notable for its stores-within-the-store like Bake Me Pretty.
Cummington
-The Old Creamery Co-Op, in turn, should be visited for its incredible menu of deli sandwiches, its list of local wildlife sightings, and the cow that stands resplendent on its roof. I had the Tempehtation with marinated tempeh, Russian dressing, Swiss, and sauerkraut on rye.
Lanesborough
-For one of the most unique, beautiful, and exciting experiences in the Berkshires make sure to make a reservation at Ramblewild, an adventure park featuring a set of treetop obstacle courses. I have a distinct nervousness around heights, but after building my confidence on the easier courses I soon found myself ziplining on a saddle across a deep ravine and, most shocking and terrifying and exhilarating of all, jumping out of a tree and trusting that science would safely get me to the dirt three stories down. It did.
Williamstown
-For gorgeous scenery closer to the ground there are a number of nice trails near The Hopper, including the easy Hopper Brook Loop or the more strenuous Haley Farm Trail. You're very near the Appalachian Trail here.
-The Clark Art Institute is worth visiting for the grounds alone (which are currently home to wonderful Thomas Schütte sculpture up on the hill), but the collection has a glorious Turner and a few other nice pieces as well. I of course also reveled in the special exhibition of Van Gogh nature paintings as a good Dutch girl would.
North Adams
-MASS MoCA is another must-stop for any art maven, with 3 floors of Sol LeWitt's wall drawings, a gallery the size of a football field, epic installations by Joseph Beuys and Mark Dion, and much much more. All set in fascinating old industrial buildings in downtown North Adams.
-Outside of town Savoy Mountain State Forest provides a nice spot for a picnic lunch or a quick dip in one of its tree-lined ponds.