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Scene & Seen: Ginger Winn at Woodstock Way Hotel Water Fall Sessions

Scene & Seen: Ginger Winn’s Intimate Performance at Woodstock Way Hotel

By Sal Cataldi | July 2, 2025

Welcome to our latest edition of “Scene and Seen,” your backstage pass to all the buzz-worthy moments in the Hudson Valley and Catskills. From funky festivals to chic soirées, we’re here to spotlight the stylish crowds, cool happenings, and one-of-a-kind vibes in our lovable communities. Didn’t make an event? No worries—we’ve got the highlights, the head-turners, and the can’t-miss moments just for you. Today we’re covering local singer, songwriter, Ginger Winn and her magical music event in Woodstock, New York: The Waterfall Sessions II. 

One of the Hudson Valley’s most buzzed-about singer-songwriters, Ginger Winn,, marked the release of her new album, Freeze Frame, with an outdoor performance in the spectacular courtyard of the Woodstock Way Hotel on Friday, June 13.

Scene & Seen: Ginger Winn at Woodstock Way Hotel Water Fall Sessions

The event, entitled Waterfall Sessions II, was a reprise of a concert Ginger undertook last June to mark the release of her acclaimed debut disc, Stop-Motion, which unfolded on a stage set in front of the picturesque waterfall on the hotel property. Here’s a behind-the-scene peek at the band and team just before the show.

Ginger Winn's album release event: Waterfall Sessions II at Woodstock Way HotelBehind-the-scenes at Ginger Winn's Waterfall Sessions II at Woodstock Way Hotel

Behind-the-scenes at Ginger Winn's Waterfall Sessions II at Woodstock Way Hotel

It’s showtime! Ginger Winn approaches the stage.

Ginger approaches the stage at the Waterfall Sessions II at Woodstock Way HotelGinger approaches the stage at the Waterfall Sessions II at Woodstock Way Hotel

Winn performed an emotionally charged 90-minute set boasting 20 songs in total. These included originals from her new album and her critically acclaimed debut, along with three smartly curated covers: Mazzy Star’s “Fade Into You and “The Weight and “So Long by Woodstock legends The Band and The Lumineers. The latter track was helmed by David Baron at Utopia Studios, the producer of Ginger’s debut disc. Winn was supported by a top-flight band, including Freeze Frame’s producer and co-writer A.J. Yorio (guitar), Lee Falco (drums), Will Bryant (keyboards), Ben Zwerin (bass), and Chris Pasin (trumpet).  

Ginger Winn band performing at the Waterfall Sessions II at The Woodstock Way Hotel

“This show felt like a hug from a friend with beautiful weather, beautiful faces, and music that connected us all, says Winn. “I’ll never forget the way it felt to share these songs for the first time with everyone. To all who came, thank you. The kindest thing you can do for an artist is to listen. And I truly appreciate all who stayed with us for every note of the show.”

“This show felt like a hug from a friend with beautiful weather, beautiful faces, and music that connected us all, says Winn.

Attendees were not only nourished by Ginger’s songcraft but also by food and refreshments provided by Catskill Mountain Pizza Company, Moonrise Bagels, BjornQorn, WAVA water, Halfday Iced Tea, Boxed Water, and more (see full sponsor list below).

The audience taking in the show at Ginger Winn's Waterfall Sessions II at Woodstock Way Hotel

The audience taking in the show at Ginger Winn's Waterfall Sessions II at Woodstock Way Hotel

Of her new album, Winn adds: “Each song represents a different shade of love, loss, and grief. My hope for Freeze Frame is that it feels like a friend sitting beside you, especially if you’re navigating loss or heartache. You don’t have to go through it alone.”

Tina Baione, the co-founder, with her husband Matthew, of Winn’s label, Keep Good Company Records, concurs. 

“We are eternally grateful to our sponsors, collaborators, and the incredible band for bringing this album to life in such a gorgeous space. A big thank you to all who came out to support Ginger and her art as she premiered her second album. It was a beautiful night and the perfect environment to experience this album.”

Aj, Matt, Tina and Ginger after the show at the Waterfall Sessions II

Matthew Baione, who also collaborates with Winn as her lyricist, continues: “This album is the evolution of Ginger Winn as an artist and as a person. Like her first album, it is meant to be played straight through and listened to as a cohesive experience. Enjoy it like you experience life – through the highs, lows, and everything in between. Every time you listen, you will find more hidden gems. Ginger and producer A.J. Yorio, with the help of Justin Guip and Tom Fattorusso, made a true masterpiece. 

Ginger Winn Album Release event "The Waterfall Sessions II" at Woodstock Way Hotel

That’s a wrap. See you next year!

Photos by Brooklyn Zeh | Follow Instagram > @brookynzeh

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INSIDE+OUT Upstate NY was thrilled to join Woodstock Way Hotel, Nourish and Atwood as PRESENTING SPONSORS and Christina Ahouse, Platinum sponsor.

Additional sponsors include:

Apres L’Amour
Bjorn Corn
Boxed Water
Catskill Mountain Pizza Company
Genevieve Geaney
Half Moon Cafe
Halfday Iced Tea
Hudson Valley 1
Moonrise Bagels
Reminders To My Future Self
Rewind Kingston
Soma Grove
Sound Future
Staples
Stockades Strategies
The Concert Chronicles
The Department of Things
Tinker Street Tavern
WAVA Water
West Kill Supply

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

Keep Good Company Records  @keepgoodcompanyrecords

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To get to know more about Ginger, check out these exclusive interviews and features. 

Ginger Winn’s New Single “Freezing” Sets the Stage for Sophomore Album

Ginger Winn: Ex-Pastry Chef Cooks Up Sweet-Sounding Debut Disc in the Hudson Valley

Ginger Winn Salutes Iconic Beatle John Lennon with New Single: Dear John

How to Coddiwomple Your Way Across the World

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