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Hilltown Hootenanies

A meandering trip through the Berkshires’ venerable hidden music clubs, listening rooms and speakeasies

by Ali Hibbs on June 14, 2012

Guthrie Center

2 Van Deusenville Road, Great Barrington, Mass., (413)528-1955, guthriecenter.org.

“Alice didn’t live in a restaurant. She lived in the church nearby the restaurant,” rambled Arlo Guthrie in “Alice’s Restaurant Massacree,” the song that both helped Guthrie stake his career and put Great Barrington’s Trinity Church on the geo-musical map. Having returned home to the Berkshires in 1965 after an ill-fated attempt at college in Montana, Guthrie moved in with Alice and Ray Brock, whom he knew as teachers from his high school, the Stockbridge School. After the Thanksgiving Day littering-arrest-turned-draft-avoidance saga, immortalized in the song and 1969 movie, the Trinity Church was purchased by Guthrie in 1991 and transformed into the Guthrie Center, an interfaith church and musical hub.

These days, the Guthrie Center’s Troubadour Series is a major stop on the folk circuit, with concerts held every Friday and Saturday night. This summer, Maria Muldaur, Tom Rush, Dan Bern, Tom Paxton, John Gorka and a bunch of others are slated to perform. All this during the centennial celebration of Woody Guthrie, which was celebrated last weekend at the center with a ton of Berkshire musical talent and several generations of the ever-growing Guthrie clan.

Gypsy Joynt Cafe

293 Main St., Great Barrington, Mass., (413) 644-8811, gypsyjoyntcafe.org

The story of how the Weller family ended up running their place in downtown Great Barrington deserves a rambling, digressive folk tune of its own—not to mention an Arlo Guthrie cameo. Keith and Lori Weller were running a restaurant in Goldsboro, N.C., when their son Jordan got interested in Arlo’s music, insisting on going to see him perform in Alice’s church. After visiting for a performance in 2007, the family (including five kids, a son-in-law and three grandchildren) decided to relocate their restaurant/café/music venue to the Berkshires in 2009.

In addition to a full-service menu, reliant upon local organic ingredients, the café includes a busy club schedule, booked by Jordan and featuring an ecclectic mixture of folk, blues, rock and world music, not to mention a weekly open mic and a consistent roster of up-and-coming Berkshire talent.

Dream Away Lodge

1342 County Road, Becket, Mass., (413) 623-8725, thedreamawaylodge.com.

“Never think your GPS is smarter than you,” warns the Find Us page on the Dream Away website in a desperate plea for you to use their stated directions. It’s good advice, because the storied venue is notoriously hard to find but well worth the adventure. Legends abound surrounding this farmhouse at the edge of October Mountain State Forest, the oldest of which being that it had been a brothel and speakeasy during the Great Depression, run by Mama Maria Frasca and her three daughters. In 1975 the venue earned a newe crop of legends when the likes of Bob Dylan, Joan Baez and Allen Ginsberg began frequenting the place, earning it a spot in Dylan’s film Renaldo and Clara.

In 1997, Daniel Osman bought the place and continued its legacy. Featuring public gardens, a meditation labyrinth and hiking trails, the resturant is a supremely intimate music venue, featuring an impressive roster of musicians content to play for dinner and tips. Everyone from Pete Seeger to Sean Rowe have passed the hat around the Dream Away with local regulars including Bobby Sweet, Robby Baier and Hector on Stilts, as well as national visits from the likes of Vetiver, Hammel on Trial and more. Summer is a prime time to find the Dream Away, but any Wednesday night all-year-round will do for their half-century-old acoustic “hootenany.”

Down County Social Club

Stagecoach Tavern,864 S. Undermountain Road, Sheffield, Mass., (413) 717-7476

While the Dream Away once had to hide this status, the Down County Social Club, located in the basement of Sheffield’s Stagecoach Tavern, prides itself as “the Berkshires’ only speakeasy.” That is, it’s a cozy spot full of eccentric characters sipping on hard and soft beverages alike, perhaps playing chess. Tommy guns and ukuleles are optional. But the only night you’ll be able to gain admittance is Thursday, when the Tavern gives proprietor Heather Fisch run of the place, cooking tapas, serving drinks and hosting special theme nights and musical performances. This isn’t the kind of place that posts a calendar of upcoming performances. You’ll have to rely on word-of-mouth—social networking at best—to find out what’s going on any given Thursday. But the most appropriate thing to do would be just to drop by.

The Lion’s Den

The Red Lion Inn, 30 Main St., Stockbridge, Mass., (413) 298-5545, redlioninn.com.

Garrison Keillor is always quick to lavish praise on the Red Lion Inn when he brings his live radio show to Tanglewood every summer. But Keillor is only one of many high-profile guests to make Stockbridge’s iconic Red Lion Inn a destination. The stately 18th-century hotel is a staple of the region’s tourism industry—and it’s also home to one of the region’s most active evening music spots.

The Lion’s Den prides itself on offering live music every night of the week, regardless of the season, never charging a cover at the door. Folks like David Grover, Chandler Travis and Mark Nomad are regulars on the Lion’s Den stage, but it’s not unheard-of for the venue to score larger names like James Taylor, who are in-town and eager to take advantage of the venue’s intimate environs.

Mission Bar and Tapas

438 North St., Pittsfield, Mass., missionbarandtapas.com.

“The food is awesome and they have microbrew beers on tap I’d never even heard of,” gushed one Albany-area musician after his first gig at Mission, a bar and restaurant at the center of Pittsfield’s burgeoning cultural scene. The place prides itself on its locally sourced Spanish-inspired tapas menu, extensive Spanish wine list and diverse beer selection (I especially like the “Mission Black Ribbon” deal, featuring four ounces of whatever’s darkest on tap along with a bottled PBR), but it’s the twice-weekly Songwriter’s Room series that landed these guys on this list. An extension of Pittsfield’s Word X Word festival, the series features up-and-coming musicians every Wednesday and Sunday night. Factor in a Monday night jazz scene and a Tuesday night open mic, and the Mission is rapidly becoming one of the region’s busiest venues.

Y Bar

391 North St., Pittsfield, Mass., ybarpittsfield.com.

While it’s slightly outside the parameters of this music-centric list, we’d be remiss to mention Mission and not its sister venue Y Bar (pronounced ee-bar). Unlike most cities, large or small, one of Pittsfield’s most vibrant cultural communities is its literary scene, and Y Bar is one of its prime gathering places. Every Tuesday night, the Writer’s Room provides a forum for authors and poets to share their work, a series that—naturally—dovetails nicely with Pittsfield’s Word X Word Fest.