About The Gypsy Blues Bar
Est. 2003 • Grit, Guts, and Good Times Ever Since
In early 2003, Clay Bearnson and Robin Bittinger weren’t bar owners—they were just two young, scrappy staffers working shifts at a beloved-but-fading Medford dive called The Gypsy Blues Bar. Then, out of nowhere, their boss asked if they wanted to buy the place.
They said yes.
With no savings, no plan, and no idea how they’d pull it off.
But they did it anyway.
What followed is one of Medford’s great love stories—between two people, their community, and a bar that’s become something much bigger than just a place to drink.
Riverside Beginnings (2003–2008)
The original Gypsy sat on North Riverside Avenue and was, in Clay’s words, “a sinking ship.” But they took the keys and rebuilt it from the inside out, transforming it into a cozy, chaotic, welcoming little bar with cheap beer, great bands, and an atmosphere that didn’t care what you looked like or who you loved—as long as you were kind and could carry a tune on karaoke night.
Robin ran the show with her signature mix of warmth and no-nonsense leadership. Clay was the big personality booking music and shaking hands behind the bar. Together, they fostered a place where outcasts, regulars, misfits, and musicians felt like family.
The rent was brutal, the roof leaked, and the oven was a microwave. But somehow, it worked. The Gypsy found its people. And its people kept coming back.
West 8th Street Era (2008–2021)
By 2008, with their lease expiring and hearts set on something bigger, Robin and Clay borrowed everything they could and moved The Gypsy to 205 W. 8th Street—an old radiator shop they gutted with their own hands.
They expanded the kitchen, installed 31 taps, and built a real music stage. It wasn’t glamorous—it was real. And people loved it for that.
Weekends were packed with local bands. Weeknights featured karaoke, open mics, and themed dance parties. The walls were covered in music memorabilia, strange signs, and stories.
Robin cooked. Clay booked. Lexi, Robin’s daughter, grew up enjoying her parent's establishment every year at the annual Christmas party. Years later, she’d be behind the bar herself—making it a true family business.
The Gypsy became a dive bar with soul. A haven for Medford’s LGBTQ+ community. A spot where city councilors rubbed elbows with punk rockers. A bar with enough heart to survive the Great Recession and a whole lot of late rent.
And then came COVID.
Weathering the Pandemic
When lockdowns hit, it was terrifying. Clay and Robin had to furlough their staff, scramble for grants, and set up tents in the street to keep the bar alive. They leaned on each other. They leaned on the community. And they made it through.
Clay—who was serving on Medford’s City Council at the time—helped craft relief efforts, stayed compliant with safety rules (even when it wasn’t popular), and fought to keep downtown businesses afloat. Meanwhile, Robin kept the bar running under impossible conditions—serving food out of a limited kitchen and checking in on staff like a den mother.
What they realized through all of it was simple:
They needed to own their space.
No more landlords. No more maybes.
Just a forever home for The Gypsy.
Grape Street and Forever (2021–Today)
After three years of planning, loans, renovations, and grit, Clay and Robin opened the doors at 111 S. Grape Street—a permanent, expanded version of The Gypsy, with more room for music, community, and weird décor than ever before.
There’s a firepit patio.
Every seat faces the stage or bar.
A mural of the Gypsy herself watches over the building.
And the spirit? Still the same.
Robin is still the heartbeat of the operation—managing staff, booking acts, chatting with regulars, and commanding respect. Clay’s still the promoter, planner, and fixer—running karaoke, organizing trivia, and DJing drag night when needed. And Lexi? She’s still behind the bar, part of the next generation keeping the vibe alive.
The Owners: Partners in Life and Liquor
Robin Bittinger is the kind of boss who teaches, protects, and leads by example. She’ll cook you a burger, remember your dog’s name, and cut you off with a smile if you’ve had one too many. She runs a tight ship, loves her people fiercely, and has built a staff culture so loyal it feels like a second family.
Clay Bearnson is the bigger-than-life character you probably saw at City Hall, onstage at a local benefit, or fixing a leaky pipe before hosting trivia night. He served two full terms on Medford’s City Council, ran for mayor twice, and brought that same civic-minded fire to everything he does—whether it’s booking a band or advocating for housing reform.
Together, they’ve raised a child, a bar, and a downtown.
More Than a Bar
The Gypsy Blues Bar is Medford’s loudest, weirdest, warmest second home. It’s a karaoke bar where everyone gets a standing ovation. It’s a music venue where local artists get their start. It’s a brunch spot with mimosas and punk rock. It’s a Pride ally, a community hub, a Halloween destination, and a downtown anchor.
It’s not just a place to drink. It’s a place to belong.
And that’s because of Robin and Clay.
Come in.
Bring your voice.
Stay a while.
You’re family now.