Live Music

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

Ease into the new year with an evening of live music from singer-songwriter and cover artist Jeff Kloetzel. A well-loved presence in the region, Jeff is known for his rhythmic guitar style, smooth, soulful vocals, and an easygoing stage presence that creates an inviting atmosphere from the first song. His sets thoughtfully blend familiar favorites ... Read more

Sterling 2 is a duo born from the group Sterling Jazz, featuring vocalist and percussionist Margaret Reno alongside keyboardist and vocal harmony specialist Noah Widoff. Together, they perform an eclectic mix of timeless favorites—drawing from jazz standards, R&B, blues, and a touch of pop. With Sterling 2, what you hear is completely live and authentic. ... Read more

We’re delighted to welcome back John Ivey, a multi-talented musician and artist whose creativity is reflected in every part of his life. As diverse as his music, John’s background includes time as a paraglider pilot and instructor, cabinet maker, contractor, and now a skilled luthier—crafting instruments with the same care and artistry he brings to ... 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

Sunday Music Magic with Crutcher and Dunsmoor! Join us for an unforgettable afternoon as Allen Crutcher and Gary Dunsmoor take the stage together, fueled by their shared passion for music and songwriting! Allen, a talented multi-instrumentalist, weaves beautiful stories through his artfully crafted lyrics, capturing the essence of love, friendship, and the joy of life ... Read more

Settle in for a enjoyable Friday evening at Pebblestone Cellars, where live music and fine wine come together beautifully. We’re excited to welcome local favorites Shybo and Twisted Vines to the stage, bringing their smooth, easy-listening sound to the winery. Featuring the soulful vocals of Shybo Torres and the groovy bass lines of Jeff Avila, ... Read more