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But it's more than historical glamour that draws a delightfully diverse mash-up of patrons to the mountain year after year to celebrate Thanksgiving. The restaurant's quirky, inclusive charisma speaks equally to camo-clad hunters, well-heeled weekenders, and assorted Guthrie offspring who wouldn't think of piling on the cranberry sauce and stuffing anywhere else. "It had always been a place where the locals were drinking longneck Buds on the porch and Leonard Bernstein was sipping fine red wine inside," Osman says proudly. In such an environment, where people who would never otherwise cross paths sit elbow-to-elbow, unconventional traditions take root. "My friends and I have always created our own holidays," says Osman, who calls himself a "gay orphan" (by this he means his biological family's house wasn't always the most hospitable place to celebrate the season). The Dream Away offers refuge from the oppressive idea that holidays must involve feasting with one's passive-aggressive mother and/or drunken uncle.

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."

Next: Their one-of-a-kind Thanksgiving experience

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