"There's probably a high chance I cry a lot," he told the small crowd, pressing the backs of his hands to his eyes and emerging with a grin.
It was the first time in over two years that Mendes, the 26-year-old Canadian pop star, had performed in front of an audience, after he abruptly pulled the plug on his career at its pinnacle.
In 2022, amid what he called a mental health "breaking point", he cancelled a multi-million-dollar, two-year international tour - more than 80 scheduled arena dates - acknowledging that, in that moment, he could not handle it.
It was a startling admission, especially for a multi-platinum male artiste with a hugely devoted young fan base.
In the time since, Mendes - a social media phenomenon with model looks, who found immediate chart-topping success as a teenager - stepped almost completely away from music, seeking stability and a life away from the road.
Then he slowly winched his way back to songwriting, through the wilds of adulthood. Over rootsy guitar and strings, his struggles are laid bare on his fifth album Shawn, due Nov 15.
"I don't understand who I am right now," he whispers on the anguished opening track.
He is not the type to mask anything. And it took him a long while to feel strong enough to make the record. "I felt super, super lost," he said.
In Woodstock, he talked of spiralling anxiety.
But in the few months since that gig, Mendes' stages have been growing exponentially. In September, he blasted through his new lovelorn ballad Nobody Knows at the MTV Video Music Awards, ending it in ecstatic guitar peals. He then sang to 100,000 people in Portuguese - at the Rock In Rio music festival in Rio de Janeiro.
At an interview at his favourite recording studio in bucolic Rhinebeck, New York, where he worked on the new album, he seemed as if he had regained the muscle memory of what it means to be a star. But he wore it lightly.
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