Before it became a brand, the Berkshires was a state of mind. If you're searching for that now mythic land where Alice's Restaurant was not just a song but a place where hippies congregated, you can start at Race Brook Lodge in Sheffield, MA. Owned by David Rothstein, an architect who once worked as a model-maker for Louis Kahn (whose reputation as a visionary was cemented by the documentary My Architect), Race Brook Lodge offers its guests a funky, crunchy-granola ambiance along with farm-to-table cuisine at its sister restaurant, the Stagecoach Tavern, which is managed by Allegra Scott Graham, Rothstein's longtime partner.

Once a Young Turk who staged outdoor folk and rock concerts in Lenox at the legendary Music Inn during the 1970s, Rothstein is now a rumpled raconteur, a grand seigneur who drives a 1980 Mercedes fueled by bio-diesel from his restaurant's kitchen. Over the past twenty years, he has carved up the 200-year-old barn into 15 bedrooms (he lives on the top floor beneath the cupola) and renovated rooms in other buildings on the property so now there are 32 guest rooms. There's also an entertaining barn—brought over in pieces from New York State on a flatbed truck and reassembled in a post-modern fashion—that is rented out for weddings and retreats. "Our first retreat was with the Hoffman Quadrinity Process, and they have been coming back five or six times a year for a decade," says Graham. "We also get a group from the Harvard School of Public Health."

Staying at Race Brook Lodge, which is adjacent to Mount Everett State Reservation and the Appalachian Trail, is like spending the night with slightly eccentric, intellectual friends who have more dash than cash. There are no telephones, TVs or minibars in the rooms, though there is an honor bar in the main barn where guests can help themselves to a beer. Graham has decorated the guest rooms with style on a shoestring. "I discovered tag sales, and little by little I've patched up the rooms," she says. "I'm always making do. I've never been able to do an entire room from scratch."

These days, Graham focuses most of her attention on the next-door Stagecoach Tavern—a quintessentially New England restaurant with an arty flair—that Rothstein purchased about seven years ago. "I bought the building for its guest rooms and we planned to rent out the restaurant to someone else, but that did not work out so we took it on ourselves," he says. They hired Dan Smith of John Andrews as a consultant in the beginning, and eventually hired Smith's pastry chef, Sarah Dibben, as the chef. "Sarah has worked very hard to make us a farm-to-table restaurant," says Graham, who notes that Bjorn Somlo (before opening his highly regarded Nudel) ran the kitchen while Dibben was on maternity leave. "Sarah has given the restaurant a vibrant and heartfelt connection," says Graham. "She supports our local farmers, and we sponsored a dinner for them last year out on our porch. Her new Sunday Supper menu, which changes every week, has really caught on."

Rothstein and Graham have endless projects. They are planting an herb and cutting garden. "We want to grow all our own flowers for our guest rooms and restaurant," says Graham, who is constantly tweaking the look of the dining rooms with flea market finds. Rothstein is "de-junkifying" and rebuilding the greenhouse that he hopes can be used as a dining room. He's forever working on his boat, a 44-foot 1940 Elco Cruisette that he used to dock at New York's 79th Street Boat Basin, which now sits under a tarp in the middle of the property along with a 1940s tractor that he's repairing. "David grew up on a farm in New Jersey, and he's uncomfortable if there aren't a few pieces of rusted farm equipment lying around," says Graham.

Rothstein's thinking about organizing some reunion concerts this summer to commemorate the 40th anniversary of the Music Inn, which opened with Arlo Guthrie and introduced a young James Taylor to the Berkshires in 1970. (When he bought Music Inn, it had been abandoned after being a hot spot for jazz in the 1950s, which is the subject of a documentary that his son Casey Meade Rothstein-Fitzpatrick helped make.) He is still at heart a music impresario who plans to resuscitate the Stagecoach basement as the Down County Lounge. Meanwhile, Graham runs the front of the restaurant, he chats up guests, an engaging eminence grise, who's on call to fix a leaky pipe or electrical short on a moment's notice. "David," Graham says affectionately, "is our roving bon vivant." Race Brook Lodge & Stagecoach TavernRoute 41, Sheffield, MA; 413.229.2916/413.229.8585 Summer rates: $105 -$290