Waterfall Sessions brings music, community and conservation to Woodstock – Hudson Valley One

There is nothing better than summer in the Hudson Valley: sitting next to a creek in the woods, watching the wisteria bloom and the buds on the trees turn into green leaves that blanket the rolling hills. But there is one particularly special summer evening in the Hudson Valley in mid-June: In the center of Woodstock, alongside Tannery Brook Falls, is a stage akin to a living room outdoors, surrounded by lush woods, string lights and a little bit of magic.
Founded in 2024 by Keep Good Company Records, Waterfall Sessions is an annual outdoor concert on June 13 bringing together emerging and established artists in one of the most iconic music communities in the world, celebrating the Hudson Valley’s musical identity and its long history of creativity, collaboration and community. Rooted in community and connection, the series is presented by a handful of national and local collaborators: Sound Future, Connect HV, Atwood Magazine, Catskill Crew, Phish on Philm and nourish.
Keep Good Company began as a creative consultancy, working with hospitality groups and various clients in entertainment until they stumbled upon Ginger Winn, a singer-songwriter, multi-instrumentalist and producer they met on Upwork. Matt, a writer and attorney, had written a poem that Tina wanted to turn into a song when looking for an anniversary present. That song would become “Super 8” — the first single of Winn’s career — and ignite a creative partnership between the Baiones and Winn. In fact, they believed in her so much that they started an entire record label branch to sign her.
Winn, born and raised in Charleston, flew to New York for the first time with plans to record music: Boiceville, to be exact, where her debut album, “Stop-Motion,” was produced, mixed and mastered by David Baron at his legendary Sun Mountain Studio. She planned to return to South Africa after recording, where she was living and creating music with a producer she met online. She never went back.
Winn looked for apartments in the city, but as she spent more time in the Hudson Valley, she realized she could do everything she needed for her music career while living here — something many musicians and artists have been realizing lately. Turns out, the Hudson Valley is an easy sell.
The Baiones came up with the original concept for the outdoor show before Winn had even gotten in the studio to record her first album. “We were meeting [David] Baron to talk about the album. We were sitting in the living room in the hotel room looking at the waterfall when I said to Matt, ‘Imagine how cool it would be to have a show here,’ and we started talking about what it would look like. We dreamed up the whole thing, pitched it to the hotel a few months later and produced the show,” said Baione.
The outdoor stage — an eclectic and retro display with flower vases, rugs and lamps — complements the rushing waterfall that sits directly behind the stage. The evening begins at 6 p.m. with a pre-show experience featuring local artists, a seed bar by Hudson Valley Seed Co., a flower bar by Adelaar Farms + Blooming Boutique Florist, lawn games sponsored by Soma Grove and tables by local artists and publications like Hudson Valley One, ConnectHV, Atwood Magazine and nourish.
The show was created to nourish the community around it — physically and metaphorically — but the partnership they began last year with Sound Future, a nonprofit leveraging the power of live events to restore the environment, transformed the concert into something bigger than music alone. Last year’s event helped restore more than 42,000 oysters in the Hudson River through the Billion Oyster Project, equating to millions of gallons of water filtered annually while supporting native fish species.
After the very first Waterfall Sessions, Ginger Winn met Byron Isaacs at a local bar while he was in Woodstock recording with The Lumineers at Utopia Studios in Bearsville. The band was working on material for what would become “Automatic” alongside David Baron and Pete Caigan. What started as a casual late-night meeting became another thread in the increasingly interconnected world surrounding the festival.
This year’s concert sees the addition of Lost Leaders, the talented duo of Peter Cole (Lava Baby) and Byron Isaacs (The Lumineers). The addition feels especially fitting given how rooted Lost Leaders are in the Hudson Valley music community. Cole and Isaacs spent years collaborating through projects connected to Amy Helm, Ollabelle and the extended Levon Helm world. The pair became close through the collaborative culture surrounding the legendary Midnight Rambles, where musicians drift between projects, sit in on one another’s sets and build lifelong creative relationships.
Isaacs has spent the better part of the last year touring internationally with The Lumineers on massive arena and stadium dates across the world before briefly returning home to play select shows with Lost Leaders, including a run opening for The Wallflowers, led by Jakob Dylan. Now, in a short break before heading back out with The Lumineers, Isaacs will bring that same energy to the waterfall stage in Woodstock. “We love Woodstock and any excuse to play there, but this outdoor show will be especially cool — at the waterfall, and on a Saturday night in June,” said Isaacs.
In 2024, Keep Good Company partnered with Rewind Kingston and Reminders to My Future Self to create nourish, a zine showcasing the various ways creatives in the Hudson Valley nourish, whether through music, art or the world around them. They partnered with the online-only indie magazine Atwood Magazine for a Waterfall Sessions collaborative edition titled “For the Love of Music,” the independent magazine’s tagline and first-ever print magazine. Mitch Mosk, the creator of the cult-followed magazine known for introducing some of the most exciting new indie artists, had just moved upstate to Beacon and was looking to get involved in the blossoming Hudson Valley music scene.
That spirit of connection is exactly what Keep Good Company described in a recent interview with Atwood Magazine: “Our name is the philosophy behind everything. We create opportunities around creative people and open doors wherever we can. If we can’t get through the front door, we find a side door. If we can’t do that, then we build one ourselves.”
Waterfall Sessions feels like the physical embodiment of that philosophy: The first two Waterfall Sessions quickly became one of the Hudson Valley’s most unique independent music events for its intimate atmosphere and collaborative spirit that feels less like a formal concert venue and more like stumbling into the world’s most magical backyard gathering.
Both years were fully recorded and filmed live, turning each Waterfall Sessions into both a concert and a time capsule of the creative community surrounding it. The live recordings were mixed by Pete Caigan of Utopia Studios in Bearsville before later being pressed to vinyl. This year, the series partnered with Citizen Vinyl, whose sustainable bio-vinyl process pushes the environmental mission of the event even further.
Returning for his third consecutive Waterfall Sessions appearance is Will Bryant, Byron Isaacs’ nephew and one of the most respected keyboard players working in Americana and roots music today. Bryant has quietly become part of the fabric of the event after appearing during both previous sessions. Trumpeter Chris Pasin also returns for a third year after performing on both of Ginger Winn’s albums and becoming a recurring presence within the Keep Good Company orbit. Local photographer Brooklyn Zeh will be returning for the third consecutive year to capture the event, a frequent collaborator of the label and a talented local artist who grew up in the Woodstock community. Much like Bryant and Pasin, Zeh is not only a creative collaborator, she is a friend.
Waterfall Sessions is a love letter to everything that Woodstock is — and the only concert to ever be held at the creekside boutique hotel since Woodstock Way opened in 2018. Woodstock has become a special character in Winn’s musical journey: The lyrics for the opening track of her debut album were written at Woodstock Way Hotel, Winn lived at the hotel intermittently during her one year of nomadic living after leaving South Africa to make the album with Baron, and she debuted her first two albums on their release days with concerts in front of the waterfall. Throughout the past three years, Winn has not only grown up alongside the waterfall but created a community around it.
Sound Future says it best: “Join us in creating a world where gathering does good.”
Karlie Flood is a 28 year old writer and artist born and raised in Kingston. You can find her at her thrift store Rewind Kingston owned and operated by her family, writing, painting, or collaging for her project called Reminders To My Future Self, or working as a director of creative strategies for the record label Keep Good Company Records.




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© 2022 Ulster Publishing
© 2022 Ulster Publishing

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