Friday November 6, Pearl Moon Woodstock NY, RESERVE HERE
THE PEARL MOON SESSIONS ft Brad Cole & Bossa Blue. This month’s special guest, woodwinds master Jay Collins. It’s been a couple years since Jay has been on stage with us and we have put together some crazy shit arrangements that I believe will blow all our minds :)
The Pearl Moon Sessions is our supper club dinner and dancing show. Great stage, great sound, great hang at the bar and the food is amazing. We will be back every first Friday of the month with different guest artist, new tunes and some guilty pleasures. As we head into winter, remember, this is your spot in the Hudson Valley to stay warm and be cool.

The Pearl Moon Sessions brings Brad Cole & Bossa Blue to Woodstock for a First Friday residency built around great songs, fearless arrangements, and an irresistible groove. Moving fluidly through bossa nova, samba, rock, soul and jazz, the band reimagines familiar favorites alongside Cole’s original music. No two evenings will be quite the same: special guest collaborations, newly debuted songs, and the occasional “guilty pleasure” will keep each show fresh and surprising. Designed for dinner, dancing, and close listening, The Pearl Moon Sessions offers locals and visitors a gathering—and a reason to make First Friday a tradition.
Cole says, “We want The Pearl Moon Sessions to feel like a monthly gathering—something familiar enough to become a tradition but different enough that you never quite know what you’re going to hear. At the heart of it is extraordinary musicianship—the kind of players who can take a song somewhere completely unexpected. We’ll bring in friends, try out new songs, revisit music we secretly love, and give these musicians room to stretch out, take chances, and let the evening develop its own vibe.”
Monday Night Record Club is an ongoing series of live studio recordings from the Hudson Valley. For the past few months, Award winning singer songwriter Brad Cole and his band Bossa Blue has been getting together every Monday night to write, rehearse, and shape new songs. Their collaborative genre-blending sound is on full display here.
These sessions are recorded live — no overdubs, no polish — just the band playing the music as it comes together. What you hear are the songs in motion: evolving, tightening, and finding their final form.
Each episode captures a moment in that process — a snapshot of a song becoming a record.
New episodes premiere the first Monday of every month.
Head to the series page and come along for the ride.