Live Music

We are thrilled to welcome singer-songwriter Holly Gleason back to Pebblestone for another unforgettable performance. Holly will be joined by Dr. J, (Jeffery Judkins) whose skill on guitar and dobro (a type of resonator guitar) that adds rich depth and texture to their sound. Together, they will be previewing several original songs from their forthcoming ... Read more

With over three decades of performing experience, Cathy Bolton brings audiences a warm, heartfelt musical style that blends folk, country, light pop, blues, and even a hint of Irish influence. She intuitively connects with her listeners, creating performances that soothe the soul and invite you to relax, sway, or even dance along. Throughout her career, ... Read more

Join us for an unforgettable evening at Pebblestone Cellars as we welcome the dynamic, soul-stirring sounds of Twelve Bars Deep. This talented group brings a vibrant blend of Blues, R&B, and swing—music that fills the room, lifts the mood, and has a way of getting everyone moving. With years of live performance experience behind them, ... Read more

Led by the dynamic duo of Joshua Jones and Shelley Kristen Jones, this talented musical pair brings over 20 years of experience to the stage. With Joshua's incredible guitar skills and Shelley's powerful voice and songwriting abilities, J O N E S is redefining the musical landscape. Get ready to rock, dance, and sing along ... Read more

Ann Kelly and Mark Ross We’re excited to welcome Ann Kelly and Mark Ross back to the Pebblestone Tasting Room for another unforgettable performance. Ann—an acclaimed vocalist and songwriter originally from California—brings a captivating blend of pop, jazz, and blues, delivered with her signature dark and soulful style. She’ll be accompanied by her husband, Mark ... Read more

Get ready for an unforgettable afternoon of music with Shine On, a talented trio bringing their own unique spin to Grateful Americana. Featuring Steve Shine on guitar, John Galloway on bass, and Cathy Dorris on drums, Shine On delivers a soulful, harmony-rich sound that celebrates the legendary music of the Grateful Dead, Jerry Garcia, The ... Read more

We are delighted as always to have Cathy back in the tasting room! With over three decades of performing experience, Cathy Bolton brings audiences a warm, heartfelt musical style that blends folk, country, light pop, blues, and even a hint of Irish influence. She intuitively connects with her listeners, creating performances that soothe the soul ... Read more

As a solo acoustic artist, Gil delivers a thoughtfully balanced set—crowd-pleasing covers everyone knows and loves, heartfelt originals that highlight his skill as a songwriter, and the occasional unexpected tune to keep things fresh. His performances go beyond music, inviting listeners into stories filled with emotion, connection, and song. In 2019, Gil released his debut ... Read more

Join us for the Jam! The Ukulele Jam is happening again! The Ukulele Jam is gaining in popularity now and is usually attended by 25 to 30 or more ukulele players strumming and singing through a number of popular songs and enjoyed by an growing audience of fans. They are great to watch but you ... Read more

Get ready for an unforgettable evening of live music with singer-songwriter and cover artist Jeff Kloetzel. A favorite throughout the region, Jeff is known for his rhythmic guitar work, soulful vocals, and engaging stage presence that instantly draws audiences in. His performances span a wide range of styles, from upbeat modern favorites to timeless classic ... Read more

Get ready for an unforgettable evening at Pebblestone Cellars as the dynamic duo, Jen Ambrose and Jon Galfano, light up the stage with their electrifying performance! Picture this: the enchanting sounds of flutes, the strumming of guitars, and the rich melodies from the keyboard filling the air, all while you sip on our handcrafted wines ... Read more

Bekkah McAlvage is an Ashland-native country-folk singer/songwriter whose music is deeply inspired by the raw beauty of Southern Oregon. Blending country, folk, and indie influences, she captivates audiences with a soulful, haunting voice and a gift for thoughtful storytelling. Her songs echo forests, rolling hills, and the free-spirited heart of an outlaw troubadour, creating an ... Read more