Ukelele Jam
2026-05-16 14:00 - 16:00 (America/Los_Angeles) | OR
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 can also sing along while enjoying a glass or bottle of wine. Local ukulele instructor Tish McFadden will again lead the jam.
If the weather is cooperative, the Jam will be held outside on the tasting room deck; spectators are welcome to enjoy the Jam from our lawn area seating.
Songbooks are available. All acoustic instruments and voices are welcome as well as just those that just want to enjoy the JAM.
Call Tish at 541-840-8075 for more information.
See you on Saturday!
May 16th, 2 pm to 4 pm

Holly Gleason
2026-05-17 15:00 - 17:00
Get ready to uncork an unforgettable afternoon as we welcome the enchanting Holly Gleason to Pebblestone Cellars! With her melodious voice and a treasure trove of diverse compositions, Holly takes us on a nostalgic journey that’s as refreshing as a crisp glass of our handcrafted wine. Her funky EP “Miracle Mile” and the soulful “Light Show” are just a sip of what to expect, as she serenades us with romantic ballads that celebrate the beauty of unconditional love—perfectly paired with every pour! With a delightful mix of sweet humor and poignant introspection, Holly’s performances are like a fine wine—starting with light-hearted banter and transitioning to soul-stirring emotions that will leave you feeling bubbly inside. So, gather your friends and join us for a night filled with music, laughter, and community at Pebblestone.
Let’s raise a glass to the beautiful melodies of Holly Gleason!
See you on Sunday!
May 17th, 3 pm to 5 pm
Reservations Recommended
Call 541-512-1655

Jen Ambrose
2026-05-22 17:00 - 19:00
Get ready to uncork an unforgettable afternoon at Pebblestone Cellars, where the atmosphere is as inviting as a warm hug and music by the incredibly talented Jen Ambrose that is sure to strike a chord. Her playlist is a unique blend of Blues, Jazz, Americana, and Rock that will have you tapping your toes and raising your glass. From her original tunes off her latest album, Plenty Of Nothin’ To Do, to beloved classics spanning from Bonnie Raitt to Led Zeppelin, there’s something for every music lover to enjoy.
Pair her mesmerizing melodies with our fine wines, and you’ve got the perfect recipe for a memorable outing! So gather your friends and family, and create some beautiful memories together because at Pebblestone, we believe that great music and fine wine make the best duet!
See you on Friday!
May 22nd, 5 pm to 7 pm

Reservations Recommended
Call 541-512-1655

Cathy Bolton
2026-05-24 15:00 - 17:00
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 and invite you to relax, sway, or even dance along.
Throughout her career, Cathy has recorded ten albums of both original and cover songs, with her work featured on two Windham Hill Records compilation albums alongside artists like Yanni, George Winston, and Jim Brickman. She’s also opened for Nashville stars Toby Keith and Dan Seals, adding to her impressive musical journey.
At Pebblestone, Cathy will share a lovely mix of her own songs and timeless favorites from artists such as John Denver, Dolly Parton, Joan Baez, The Beatles, Joni Mitchell, Bob Dylan, Emmylou Harris, Chris Stapleton, Miranda Lambert, Lainey Wilson, Mary Chapin Carpenter, and more.
See you on Sunday!
May 24th, 3 pm to 5 pm
Reservations Recommended
Call 541-512-1655

John Galloway
2026-05-29 17:00 - 19:00
https://pebblestonecellars.biz/wp-content/uploads/2026/05/Jon-Galloway.mp4

Something new is on the horizon.
A brand-new band is forming with Jon Galloway bringing fresh energy, new sounds, and a vision that’s just getting started.
Details coming soon. Stay tuned.
See you on Friday!
May 29th, 5 pm to 7 pm
Reservations Recommended
Call 541-512-1655
