Old School Good Times in the Heart of Whidbey

Walk up the stairs and through the door and you’re transported back in time—to an old-school country store, but with better beer. That romanticism is just part of the vibe. It’s also the live music, the comedy and trivia nights, the gathering of community, and the spirit of giving back that is Bailey’s unique charm.

Owner Ken Stange rented the former school building turned convenience store and gas station about eight years ago. Drained by the demands of teaching and coaching, he was ready to find another way to make a living.

“I loved teaching English and yearbook class and coaching tennis during my eleven years at Coupeville High School,” he said. “It did take quite a toll on me, though. There came a time when I didn’t quite have the passion for it I’d once had. It was time for a change.”

When Bailey’s, which had been turned into something resembling a tavern hangout, became available, Stange saw potential to turn it into something bigger.

“I started making food, having a little music. Eli Moore started playing here. He wanted to have bigger crowds and was bringing in non-local musicians. It worked well. So, we changed up the room, moved things around. We made the upper stage accessible and built the lower stage.”

Moore remembers playing at Bailey’s when the room was barely more than a covered patio, crowded with arcade games and space heaters. Other musicians and bands had played there as well. There is something intrinsic about the space; it inspires music.

For singer-songwriter Nathaniel Talbot, it’s all about Bailey’s “laid-back, DIY vibe and the fact that it’s affordable and inclusive for everyone.” Some venues can break the budget for young people and service workers, whereas Bailey’s has only a suggested donation and no drink minimum which, Talbot said, “enhances inclusivity.”

For Moore, it’s the location. “I like how remote it is. How there is not much cell reception,” he said. “It feels very old school, like the ’90s a little bit. You can kind of tune out.”

Moore and wife Ashley play in the Indie-pop group LAKE, which is plugged into a network of bands throughout and beyond the region that help each other out.

“The national and global ecosystem we are involved in has an exchange pattern where we will book shows for people and then give the majority of the money to the bands that are traveling. Then vice versa. When we are touring, they can help [book] us in their cities.”

That’s how bands like Winnipeg’s Living Hour, Los Angeles’s Mega Bog, and Oakland songwriter Stephen Steinbrink have all wound up performing at this little joint lost out in the South Whidbey woods.

In spring 2020, Bailey’s hosted a fundraiser for the South Whidbey High School (SWHS) Jazz Band. SWHS is Moore’s alma mater; in fact, Stange’s daughter Oliana played in a student band group called the Puget Sound Jazz Quintet. They were the first of six bands to play that night, raising $1,000 for the cause. Stange was looking ahead to a completely booked spring and summer for the first time, thinking “it would be the summer Bailey’s took off. Nope. Everything went on hold, but it allowed for some key pivots.”

“The next Monday was the COVID-19 lockdown,” he added. “It was slower without the pub and music, but the community came out strong for me. I had just added a fryer, which turned our really good burger into a bona fide meal. Lockdown was the point when people started discovering our food.”

When COVID restrictions loosened, musicians clamored to play again. Stange expanded the loading dock out back and turned it into a covered stage. He also invested in a PA system.

“We had a full concert schedule doing outside shows. We were drawing 30 and 40 people regularly; sometimes 80. It was bonkers,” said Stange. “It was summer of 2021 when the music calendar filled. It’s when more locals realized we were putting on excellent shows. We’d been doing it since 2016, but not many knew.”

For a small venue like Bailey’s, those numbers meant a packed house. Musicians kept coming, wanting to play out in the country.

“I have a good thing going, because I’m out in the middle of nowhere,” said Stange. “That’s the bad part, too. Every year I try to do something to make the experience better, to bring in more people.”

Musing about the appeal of Bailey’s to artists who come to play, Stange said, “It’s about the people. I’ve become friends with many of the musicians who play here. For all the thanks they give me for holding a space for people to share their music, I thank them for choosing Bailey’s—for choosing me.”

It is a thankfulness evident in Stange’s commitment to the community. He started a trivia night in 2017 and hosts the event every Thursday. In 2021, he began raising funds via trivia night for local nonprofits and over the past two-and-a-half years, Bailey’s has contributed more than $35,000 to the community.

“I’m so proud of this,” he said. “South Whidbey is special because of its sense of community. People help each other.”

Bailey’s is a true community location, rooted in place among majestic fir trees. A dedicated following packs the house for music, trivia, comedy, and island fun. So, the next time you’re on South Whidbey, take a slight detour down the winding country roads of Clinton to experience Bailey’s, “the heart of Whidbey.”

For schedule and directions, contact baileyscornerstore.com.