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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As night falls, each new gust of wind through the door brings familiar faces, some from small Berkshire towns, others from New York City or Boston, all anticipating the big night ahead. "We've been working out our stomachs for weeks!" exclaims Robert Croonquist, an old friend of Osman's who now runs a New York nonprofit, as he unwraps his colorful scarf. "We've known Daniel since the big bang," interjects another regular, Emmett Foster, who arrives with a bevy of Osman's former colleagues from the famed New York Theatre Workshop (downtown incubator of Broadway-bound Tony Award winners like Rent and Once). "This is my home away from home," says Suzanne Hoch, a gamine schoolteacher in knee-high boots from New York's Westchester County who first visited the Dream Away in 1979, when she was at a summer camp nearby. "There's a great excitement that builds before a holiday here—we all text each other and send Facebook messages. We're like a bunch of kids who can't wait for Christmas morning."
Hugs are exchanged; a round of Lenatinis (vodka, vermouth, singed orange peel, named for Lena Horne) is ordered. While he's labored to keep the lodge's aesthetic intact, Osman has made one significant upgrade: the food. Five years ago, he hired Amy Loveless, a cherubic former bakery owner and locavore-before-it-was-in-fashion who handpicks the best produce and meats from the Berkshires' farmers. Loveless has augmented what Osman refers to as the Dream Away's "Yankee comfort food" menu with Vietnamese, Korean, and Moroccan influences—basically, whatever has most recently piqued her curiosity. Tonight she's serving turkey marinated for 24 hours in buttermilk, ginger, garlic, and soy sauce; citrusy green beans; and apple-cranberry crumb pie made with apples she picked herself in the bountiful Hudson River Valley. "People find a lot of comfort in a traditional Thanksgiving meal," Loveless explains, "but I like to tweak 'traditional' ever so slightly to make it a bit more fun and exciting."
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Later, in the music room, which is strewn with leather ottomans and tribal-print pillows, Paula Langton, a luminous Bernadette Peters type, strums a banjo while leading the crowd in a sing-along; Suzanne Hoch pounds ably at the piano. Langton's husband, the lanky actor Ken Cheeseman, strolls in. "Kenny," Langton says, "we've got a uke all tuned for you!" Someone starts shaking a pair of maracas.
Osman sits still for the first time since dawn. "My friends say I haven't left the theater at all," he notes with a laugh, sipping a hard-earned margarita, eyeing his mutt, Carter, who's passed out on the threadbare Oriental rug. "I still produce and direct my own show every night."
Although it's the guests, reveling in the Dream Away's uncommon kinship and warmth, who feel like the night's big stars.
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