Fairy Lights and Folk Songs: Inside Waterfall Sessions III with Ginger Winn and Lost Leaders

As summer arrives in the Hudson Valley, there’s an irresistible pull to be outside.  The light lingers, the nights feel longer, and live music enjoyed outdoors is a perfect match for the season. This is a place that has a way of calling us outdoors—into nature, into community, and into moments of collective wonder. Beneath the canopy of early summer and accompanied by the wistful, cinematic folk music of Kingston-based singer-songwriter Ginger Winn, Waterfall Sessions III offered the kind of evening Woodstock does best: joyful and deeply connected to place.

Before the stage was even in view, the light hymn of guitars being tuned led me to an outdoor amphitheater– blankets spread across the grass, friends greeting each other, children admiring the creek and the gorgeous waterfall. Long shawls, brown boots, statement hats– this spot was perfect for anyone into the true Woodstock hippie style. The beautiful and newly renovated Woodstock Way Hotel, with its rustic, contemporary architecture, was the perfect canvas for a night of art. As the players tuned their instruments out of sight, the empty stage heightened anticipation and excitement. Strolling through the hotel’s backyard area that had been transformed into a concert space– it reminded me of a small fairy village– packed with happy revelers and bouquets of colorful flowers. 

Concertgoers enjoyed tasty bags of Bjorn Corn and a massive bowl of vibrant and delicious guacamole as they settled in for the evening. From the very first strum of the guitar and the singer’s soft tapping on the mic, all of us gathered along the edge of the railing, peering down onto the fairy-light-covered stage below. Ginger Winn fit in perfectly with the scenery. Her soft, folk-inflected vocals and timeless lyrics drifted through the trees and drew the crowd in. Ginger chatted with the audience about her first solo album, Stop-Motion, and its deep roots in the Hudson Valley. One can sense how the mountains and streams of Upstate New York have inspired her lyrics– Winn’s voice cascading down like the Tannery Brook waterfall behind her. I joined a number of other happy attendees on a nearby rock wall to soak it all in, my sightline filled with friends bobbing their heads along to the guitar’s chords. Winn’s music has that kind of cinematic folk-pop vibe with echoes of Phoebe Bridgers and Hozier, making the performance simultaneously warm and nostalgic.

Lost Leaders and supporting musicians joined in with Ginger to perform a multitude of ’70s-influenced tunes, propelling me and many others to pop out of our seats and get a great view from the railing. Interacting with the audience was a strong point of these players– they excited the crowd with comments on the recent Knicks win after spotting a listener with a jersey. Their rootsy-Americana style had many of us swaying along to Byron Isaacs’ smooth bass mixed with Peter Cole’s classic voice. This duo’s partnership– stemming from works connected to the Levon Helm Band and Ollabelle– provided their music with a rich, Woodstock-inspired vibe. The added layer of a crisp trumpet perfectly complemented the smooth strums of Cole’s guitar.

Down near the stream, a woman got up to dance, and soon this lone, simple act of enjoyment motivated multitudes to follow along. I was dazzled by an exhibition of fluttering shawls and laughter.

Woodstock has long been a place where artists of every kind find an audience, and evenings like this are a reminder of how fortunate we are to experience music in such extraordinary settings. There is something undeniably magical about listening to musicians perform before a cascading waterfall—the sound of the water becoming part of the score, the surrounding woods forming a natural amphitheater. Emerging artists share new work just feet from their audience, while familiar songs seem to take on new resonance in the landscape. I returned to my favorite perch along the stone wall, a peaceful spot from which to take in the rich harmonies of Lost Leaders and the luminous vocals of Ginger Winn. As twilight settled over the falls and music filled the air, it felt less like a concert and more like a gift—one of those rare summer evenings that could only happen in Woodstock.

From the perspective of Gen Z, which happens to be my generation, we’re drawn to big stages and flashing lights. However, the evening at Waterfall Sessions III was a wonderful reminder of the importance of intimate spaces and that big things do indeed come in small packages.

This was a special night for me, as it was the first time I ventured out to see live music by my lonesome, and I couldn’t have picked a better time or place. The many friendly conversations I overheard were soothing and made me feel welcome, as was the kind woman who tapped me on the shoulder and complimented my boots, which made my night. Everything I saw, heard, and experienced made for an evening I won’t forget.

From the perspective of Gen Z, which happens to be my generation, we’re drawn to big stages and flashing lights. However, the evening at Waterfall Sessions III was a wonderful reminder of the importance of intimate spaces and that big things do indeed come in small packages. I urge you to seek out a small community festival this summer. There is something refreshing about the easygoing atmosphere, the sense of connection, and the simple pleasure of gathering around music in a beautiful place. It has a way of shifting your perspective on what a night out can be—less spectacle, more shared experience. Woodstock has always been especially suited to these moments. Around seemingly every corner, there’s a hidden nook filled with music, conversation, laughter, and the feeling that you’ve stumbled upon something special. It’s part of what makes this town such an enduring haven for artists, dreamers, and those of us who simply enjoy being together.

Follow/Connect with Ginger Winn via Website | Facebook | Instagram | YouTube | Spotify

Written by Bernadette Hughes | Photos courtesy of Keep Good Company Records

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