WOODSTOCK — The Bearsville Theater in Woodstock has always carried a sense of musical pilgrimage. Built from Albert Grossman’s original vision of a creative sanctuary in the Catskills, the theater became an anchor in a landscape that shaped American songwriting through artists like Bob Dylan and Janis Joplin. After its rebirth under Lizzie Vann’s stewardship in 2019, the Bearsville Center has reemerged as a magnetic cultural hub where new artists add their own stories into a notable history that spans generations. This Friday, that enduring lineage welcomes the Whiskey Treaty Roadshow for their first ever shows in Woodstock.
For more than a decade the Massachusetts based ensemble has become known for a live performance that blends foot stomping Americana with a generosity of spirit that pulls audiences directly into the experience. The band is built around four songwriters, Tory Hanna, Chris Merenda, Greg Daniel Smith, and David Tanklefsky, each with distinct voices and influences that merge into a singular sound. While rooted in the Berkshires and Western Massachusetts, the band has built a national presence at festivals and regional traditions, carrying a reputation for big harmonies, instrument swapping, and a joyful chaos that feels entirely intentional.
Before their Bearsville debut, I spoke with Tanklefsky, who brings a journalist’s sensibility to his creative life. His background includes reporting, radio, television production, and media writing, a path that has kept him tethered to storytelling even as music became his primary language. “I told myself I would keep one foot in journalism,” he said, explaining that he still writes essays and features when the right subject calls to him.
The Whiskey Treaty Roadshow first emerged not as a band but as a temporary experiment. In the summer of 2014, the four songwriters decided to take their individual projects on a four-night run from Western Massachusetts to Boston. The idea grew out of the Whiskey Treaty Festival in Greenfield, an event created by Hanna’s wife that gathered musicians, makers, and local vendors into a shared creative space. That sense of gathering has remained at the heart of everything the group does. Tanklefsky recalled that the early shows were a loose collection of individual sets rather than a cohesive band. Everyone brought their own songs and sometimes only a few members would play on a particular tune. The group did not yet imagine a long-term future.
A turning point came when filmmaker Tim Bradley joined the four-night run to document the trip. “That documentary ended up getting into some film festivals and then the film festivals would say they wanted the band to come play,” Tanklefsky said. What began as a short adventure became a living project. Eleven years later the band still carries that original spirit of spontaneity and community.
Part of the group’s appeal comes from the mix of backgrounds each songwriter brings. Tanklefsky says he and Hanna grew up drawn to indie rock and punk, while everyone had different degrees of connection to folk traditions. Merenda has roots in the acoustic lineage of the region and played alongside musicians deeply tied to the legacy of Pete Seeger. Smith leans toward rock and the music of the nineties. The combination creates a live show where the boundaries between genres soften in favor of energy and connection. “It all comes together in a way that is unique because we come from similar but slightly different worlds,” Tanklefsky said.
The Berkshires embraced the group early on. Folk heritage is central to the region and the band found themselves welcomed by legends and rising artists alike. They recorded with Arlo Guthrie, connected with the Guthrie family, and developed friendships that shaped their artistic community. Tanklefsky described this support as a defining part of their identity. “I think people get the sense that we love playing together and we shine the spotlight back on the people who support us,” he said.
Much of the band’s ethic is built on generosity. Their shows often serve as benefits for community causes. Their COVID era project, which raised funds for service workers, earned them recognition as Volunteers of the Year from the Berkshire Community Action Council. Tanklefsky credits former full time member Billy Keane with helping guide the band’s commitment to giving back during difficult times.
On stage the Roadshow creates what feels like a small world for a night. Instruments move from one set of hands to another, harmonies swell in unexpected places, and improvisation gives each performance its own life. Tanklefsky notes that this freedom developed gradually as the members became more comfortable leaning into the jam-oriented influences that they all share. “We all love the Grateful Dead and that side of things,” he said. “There is nothing that really matches playing together for a long time and having that musical communication.”
The group has never toured at the pace of bands whose lives revolve entirely around the road. Every member has a family, and the realities of parenthood reshape touring schedules. At the same time the band has grown steadily through festivals, club shows, and word of mouth. Tanklefsky sees this slower pace as a strength. It keeps the music sustainable, the friendships intact, and the creative process healthy. “You have to respect everyone’s priorities,” he said. “Keep everyone in the same vehicle and keep the vehicle moving forward.”
That spirit of mutual respect is a core reason the band continues to thrive. Each songwriter gets space, but every member also gives that same space away. Tanklefsky said that joining the project helped him let go of the anxieties that come with the solitary pressure of a solo career. “You get twenty five percent and the other seventy five percent is supporting everyone else,” he explained. The result is a band where the absence of ego becomes its own audible quality.
The band’s appeal reaches well beyond local listeners. Marika Romero, producer at WDST Woodstock Radio and co-producer of the Mountain Jam music festival, has become an enthusiastic supporter. “They remind me of The Band, The Bodeans, and other favorite bands of mine. I listen to Treaty often,” she said, noting how the group’s timeless blend of melody and storytelling fits comfortably alongside the legendary acts that have shaped the Catskills music landscape.
Friday’s Bearsville Theater show is not only long overdue for local audiences but a milestone for a band with strong ties to the Hudson Valley through family, friendships, and the folk lineage that shaped them. Woodstock, with its layered musical history, offers a fitting stage for a band whose identity is built on collaboration, community, and the joy of playing together.
Tanklefsky is particularly excited to finally bring the Roadshow to the historic theater. Their mix of songwriting, improvisation, and harmony driven Americana seems destined to resonate in a place built on decades of musical storytelling. With support from fans, radio personalities, regional arts leaders, and those discovering the band for the first time, the Whiskey Treaty Roadshow arrives ready to build another one of their small worlds under the Bearsville lights.
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