By Lara Tupper
Above: Lara and Bobby perform in the living room-like setting of The Dream Away Lodge

I used to be a lounge singer on cruise ships. (For the gory details, refer to my autobiographical novel, “A Thousand and One Nights.”) But then I got serious. No more sequins. No midnight buffet. I went to grad school and became a creative writing instructor at a large university in New Jersey.

Ten years later, burned out, I moved to the Berkshires to work at Kripalu Center for Yoga & Health. There I discovered kale, meditation, and the wonder of swimming in Lake Mahkeenac. One early July evening, I took a dip and heard echoes from Tanglewood, right next door. The light was fading. I was buoyed by summer, by the new life I’d carved. When James Taylor began his Berkshire anthem, “Sweet Baby James,” it felt like a nudge. I remembered how much I loved to sing.

I found I could stitch together my passions, as many creatives do here. (The Berkshire quilt, I’ve heard it called.) I began to teach independently and finished writing two books, gigging with tunes from the Great American Songbook and rock/folk harmony bands of the 1970s.

One benefit of performing in the Berkshires is that I’m less likely to get seasick. Another is the generous attention span of audience members. At first, this was disconcerting, especially in cozy listening rooms like the Gateways Inn (Lenox) or The Lion’s Den at The Red Lion Inn (Stockbridge). From behind the microphone, I could see every expression at every table, i.e. exactly who was listening and who was more invested in their chocolate cake.

I’ve come to prefer these intimate venues. At The Lion’s Den, for instance, listeners call out requests and sing along.

Couples slow dance. It feels like I’m singing to friends. I like the Den’s old-timey décor, too: red tin ceiling and white stone chimney. I think of travelers coming through during the past 251 years.

I’m lucky to collaborate with incredible musicians, including my husband, Bobby Sweet, a seventh-generation musician from Becket. I’m biased, but Bobby’s seven albums are filled with achingly beautiful songs, several about growing up here. (Many can be heard on TV shows and in films.) He’s traveled widely—on nationwide tours with Arlo Guthrie, on musical pilgrimages to Argentina and Ireland—but, most impressive to me, he’s performed in nearly every venue in Berkshire County.

The Dream Away Lodge (Becket) has been Bobby’s stomping ground since the 1980s. The 200-year-old farmhouse is at the end of a long, woodsy road. (“Where am I?” said my friend, dazed, like Dorothy landing in Oz, if Oz were October Mountain State Forest.)

The music room has a funky living-room vibe, crowded with mismatched stools and ottomans. (“The ottoman empire,” Bobby jokes.) Some claim it was a brothel and a speakeasy during the Great Depression. In any case, it feels as though many have let loose and enjoyed themselves here.

The Barn (South Egremont) is rich in history, too. Known as the Robbie Burns House during the 1970s and ‘80s (an infamous roadhouse), the barn dates to the 1830s. Current owners Jenny Rubin and Nick Keene have made The Barn a hip, popular venue for local and touring musicians. When I’ve performed there, I’ve felt like a rock star, which is to say, there’s something about The Barn’s stage that invites genuine focus and enthusiasm from the crowd. It’s become a space for true music fans. (Note—Rubin and Keene are selling The Barn, but it has a full lineup this summer and they hope the new owners will keep it going as a music venue.)

“Berkshire musicians show up for each other as audience members and as impromptu guests onstage. There’s camaraderie rather than competition. I’m part of a collective here.”

During warmer months, it’s a treat to perform outside at the Devonfield Inn (Lee) for their summer music series (June to October). Owners Doug Bagnasco and Jim DeBlasi started the free concerts in 2020 in response to pandemic closures. Bobby and I have been thrilled to hold summer residencies ever since.

Devonfield has a peaceful, picnic vibe. Guests can use the inn’s Adirondack chairs or bring their own seats (and beverages). We sing under a small canopy, facing the inn, so the audience can take in the view (a grove of birch trees framed by a vast meadow with walking trails). It feels like a mini Tanglewood.

Which brings me back to the gift of that summer evening, 14 years ago, as I heard James Taylor’s voice and vowed to use mine again.

Lara Tupper is the author of three books and founder of Swift Ink Stories, which offers writing workshops and private manuscript development. She is also a crooner who has traveled the world. Her latest album is “This Dance.”
laratupper.com