High in the Berkshire mountains, down a stretch of country road canopied by a tangle of ice-tipped spruces and pines, a white clapboard roadhouse appears over the crest of a hill. "Dream Away Lodge," reads a rickety wooden sign. The neon beer lights beckon from the 50-acre wilderness, which skirts the edge of Massachusetts's largest state forest. A turkey slowly roasts on a spit outside, churning fragrant plumes of smoke into the chilly air. Walk inside through a retro storm door and you'll find proprietor Daniel Osman manning a host's stand under a framed Marilyn Monroe nudie pinup, a swinging mix of vocal jazz classics streaming in via satellite radio. "Here's the deal," he says over the phone to a patron inquiring about the restaurant's hours on Thanksgiving. "The house opens at 3, buffet's from 4 to 6, then we party until we can't stand it anymore."

At 54, Osman, the Dream Away's self-described "sandman," has the outsize presence of the actor he trained to be—one who's found the optimum stage for his unique brand of showmanship. Through a groovy front-room bar crammed with an accumulation of snow globes and Michelob lanterns, a cozy wood-paneled dining room has been set with mismatched tablecloths and colorful vases full of orange lilies. The scent of garlic mashed potatoes wafts in from the kitchen.

The lodge's folksy, tchotchke-laden charm is the stuff of legend. Back in 1975, members of Bob Dylan's Rolling Thunder Revue—including Dylan, Arlo Guthrie, Joan Baez, and Allen Ginsberg—dropped by the former speakeasy and brothel and ended up staying all day, drinking, smoking, and making music; playwright Sam Shepard documented the whole thing in the Rolling Thunder Logbook. The place so bewitched Osman when he stumbled upon it while working the summer theater festivals nearby that in 1997 he decamped to the country to buy it (that is, once the owners had painstakingly questioned and vetted Osman, and judged him sufficiently wise to the restaurant's essence—i.e., not a land-grabbing yuppie looking for a teardown). Osman has taken seriously the task of preserving the lodge's "nostalgic hippie sweetness," as he calls it, and paying homage to its history. "There's a Sinatra rumor," he says, lowering his voice to a whisper. "A Janis Joplin legend. Liberace was certifiably here. Milton Berle..."

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