The Dream Away Lodge Is the Funkiest, Most Fanciful Restaurant Hidden in the Berkshires

Follow wooded country roads and the sound of bluegrass music to this quirky, wistful winner.

The Berkshires’ whimsical Dream Away Lodge. / Photo by Sheppard Bear

“This would be the perfect place for a wedding.”

I said it first. But across the kitschy lace tablecloth, the eager glimmer in my boyfriend’s eyes confessed that he was thinking it, too. The statement is the kind of romantic frankness you’re emboldened to exercise when you’re dining somewhere that feels particularly transportive: say, a 200-year-old white-frame farmhouse at the entrance to Massachusetts’ largest state forest, where Bob Dylan, Joan Baez, Arlo Guthrie, and Allen Ginsberg once partied—together.

To find the Dream Away Lodge—an eccentric, roadhouse-like restaurant I’d heard whispers about for years—we blind-trusted our GPS to lead us deep into the western Massachusetts woods, down dark lanes where gnarled limbs from tall trees reach to grab at low-floating headlights. The place has long attracted mountain beatniks seeking folk-music hootenannies in its wood-paneled den and enclosed porch, but current owner Daniel Osman, a former theater artist with ties to the Radical Faeries, a global gay-hippies collective, has painted yet another layer onto its long history. Now the reputed former brothel is filled with flea-market finds, irreverent tchotchkes, and evidence of proudly progressive sensibilities. (“Misogyny is not normal,” announces one poster by the front door.) Think: the B-52s’ Love Shack in the Berkshires.

What’s not camp is the entirely serious food from chef Amy Loveless, an area native who inherited a gift for rustic-American cuisine from her mother, a one-time cook for Norman Rockwell. Here, the genre is burnished with international accents: Local lamb, chicken, and pork are respectively given Greek (tzatziki!), Mexican (tomatillo-chipotle salsa!), and Korean (cucumber-ginger salad!) treatments. The food is hearty, the place happening. As we share a mezze plate by tapered candlelight, a jam band’s tunes waft over to the dining room.

After dinner, we grab stiff cocktails at the front bar—a quirky setup of glowing plastic cubes near an ornately framed Marilyn Monroe nude—then sip them around the wildflower-filled lawn’s flickering firepit with a handful of New York City finance types who know the one Brooklyn-cool place to kick it when visiting their parents’ second homes. Happy chatter rings out into the dark.

There’s still a question mark over when and where my boyfriend and I will marry. Could we even afford this? Who cares? Feasting and free under a starry sky, this is a place for dreaming.

Jacob’s Pillow performance center is now open year-round. / Photo by Christopher Duggan

The Dream Away Lodge
Miles from Boston: 135


Despite its name, you can’t actually sleep at the Dream Away Lodge. But you will rest well at Kemble Inn (starting at $395 per night) in neighboring Lenox, a gorgeously restored, 1881-built Colonial Revival mansion where plush accommodations include a stunning Ralph Lauren–furnished suite with a wood-burning fireplace.



Jacob’s Pillow—the newly year-round landmark performance center founded by modern-dance pioneer Ted Shawn—will follow up its famous summer festival, running through August, with fall “Pillow Parties,” including a Halloween drag ball.


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