
The musical mind of Jason Oberstein is split in two — one half rooted in his energetic, Garcia-inspired lead guitar work that’s been lighting up the Boston jam scene, and another that embraces a softer, more thoughtful texture with heartfelt, lyric-driven acoustic originals. On the electric side, Jason has been shredding on stage and in the studio with several local acts including Jill McCracken, Flying Turtle, and Spoondrift. On the acoustic side, he’s been sharing his intimate singer-songwriter material at coffee shops and listening rooms.
In 2024, Jason began to blend these two passions with a solo recording project. The result was Northern Rails, his debut album which features a core of thought-provoking songs, spiced up with lush vocal harmonies and a healthy portion of folk-rock and jam-psychedelia.
Now, Jason is bringing this vision to the stage with his new band, The 4th Story. Imagine hearing a song that pulls on your heartstrings and makes you cry, only to be led through the luminous caverns of group improvisation, straight to the bone-shaking climax of a mind-melting jam. Featuring an absolute powerhouse lineup of musicians, The 4th Story will do just that. Scroll down to see when the next show is!
Above all, Jason is a lover of local music, a walking dictionary of music theory, and a truly open-minded creative. With every project, he dives in head-first and strives to be one of the best guitarists Boston has to offer.
Instagram: @jason.oberstein • YouTube: @JasonOberstein

Guitar Lessons
Looking to up your guitar game? Whether you want to jam with others, shred that gnarly solo you’ve been obsessed with, or work up some classic acoustic campfire material, I can help get you there.
Upcoming Shows
| Date/Time | Venue | Project | Tickets |
|---|---|---|---|
| Tuesday, 3/3 7:00pm |
The Cantab Lounge Cambridge, MA |
The 4th Story Flying Turtle |
Free! |
| Sunday, 3/8 11:00am |
New Leaf Espresso Somerville, MA |
Flying Turtle | Free! |
| Saturday, 3/21 8:00pm | Satellite Cambridge, MA |
The 4th Story | Free! |
| Saturday, 3/28 8:00pm |
Dover, NH (dm for details) |
Jason Oberstein | Tix TBA |