By Renee Clark Quade
There’s something about an outdoor concert at Point of the Bluff Vineyards in Hammondsport, NY that puts you in a good mood before a single note is played. Keuka Lake stretching out below, the sun working its way toward the bluff, a glass of wine in hand. It’s already a good night before anyone plugs in a guitar. But on Friday night, June 13, Brothers Osborne made sure nobody was just there for the scenery.
Before the headliners even took the stage, though, Cassidy Daniels made a case for herself that a lot of openers never get to make. Just her and a guitar, no band, no safety net, and she held the crowd from the first song. That’s harder than it sounds, especially in an outdoor setting where people are still finding their seats and topping off their drinks. Daniels didn’t seem to notice. She opened with a story about a heart-shaped necklace an ex-boyfriend once gave her, joking that the gift alone told her everything she needed to know about why it didn’t work out, then launched into the song it inspired. The crowd was already laughing and leaning in.
When her guitar string snapped less than one song in, the Brothers Osborne crew immediately stepped in with one of the band’s own guitars. Daniels laughed that she’d never played anything that nice or that big, and kept right on going. She covered “Me and Bobby McGee,” talked about appearing in two episodes of Dutton Ranch and competing on The Road, and introduced “Amen Emilia,” a song she described as her honest wrestling match with faith, due on her debut album this fall. She closed with the unreleased “Crazy Love,” out June 26, and before leaving the stage warned fans she was nearly out of merch from previous shows but would be hanging around anyway for photos and autographs. For an opener working with nothing but her voice and one guitar, that’s a win by any measure.
As dusk settled in, Brothers Osborne hit the stage to a backdrop of the two brothers in silhouette and immediately launched into “All Night.” It was an appropriate opener because that’s exactly what the crowd looked like they were ready for.
What followed was the kind of show that reminds you why live music exists. The setlist moved through “Headstone,” “Weed, Whiskey and Willie” and a Tom Petty-approved energy boost with “I Won’t Back Down,” but the night was never really just about the songs. It was about everything happening between them. John Osborne was constantly working the crowd, splitting the venue into competing sections, sending guitar picks into the audience, finding ways to make a few thousand people feel like they were all in on the same joke.
The crowd itself deserves some credit here. This was one of those nights where the audience brought something back to the stage. A woman in the front row was attending her 101st Brothers Osborne show, wearing a shirt announcing she was “loading” the next generation of fans. Someone else nearby was at number 81. And somewhere in the mix was a young girl at her very first show, which the band acknowledged with a grin, joking her parents had started her at the top.
The proposal was the moment that stopped everything. A couple the band had met earlier at the meet-and-greet got invited onstage, he got down on one knee, she said yes, and the whole vineyard erupted. They celebrated with a shot alongside the band before heading back into the crowd to a roar that probably carried across the lake.
Musically, the band was at their best when they let songs breathe. A cover of U2’s “Pride (In the Name of Love)” flowed straight into “Stay a Little Longer” without losing momentum. “Burning Man” became a full-crowd singalong. And then there was “Ain’t My Fault,” which midway through an already extended jam suddenly detoured into AC/DC’s “T.N.T.” before snapping back to finish the song. It was the kind of move that makes you laugh and cheer at the same time.
Before the encore, the brothers took a minute to thank their crew, introduce their touring band, and give another shoutout to Cassidy Daniels, taking a small but pointed shot at AI-generated music in the process, praising artists like her as proof that the real thing still matters.
They came back out for “Pushing Up Daisies,” dedicated to Doug and Trish on their 36th anniversary, and closed with Alan Jackson’s “Chattahoochee,” a song that on a warm summer night in the Finger Lakes felt about as right as it gets.
Point of the Bluff has hosted some good shows. Friday night was one of the great ones.
Setlist – Brothers Osborne – Point of the Bluff Vinyards – June 13, 2026
All Night / Headstone / Weed, Whiskey and Willie / I Won’t Back Down / 21 Summer / Shoot Me Straight / Rum / Nobody’s Nobody / Not For Everyone / Pride (In the Name of Love) / Stay a Little Longer / Burning Man / Ain’t My Fault / Pushing Up Daisies / Chattahoochee
Photo Gallery – Brothers Osborne – Point of the Bluff Vinyards – June 13, 2026
Photo Gallery – Cassidy Daniels – Point of the Bluff Vinyards – June 13, 2026
