: Nik Wheeler / Alamy Stock Photo

Old-Time Charm in Oakland

Jesse Larson,  Photographer
February 23, 2018

Bette Keehley found Oakland by chance in 2006, on a road trip at a crossroads in her life.

The retiree fell hard for the quiet little town in Southern Oregon — its tight-knit community, storied history and magical frozen-in-time feel — and a year later, she was its mayor. She’s been working since then to encourage visitors to come explore and appreciate Oakland’s historic buildings — more than 90 of them, built between 1852 and 1890. In 1968 the Oakland Historic District was the first to be placed on the state’s historic register and is also on the National Historic Register.



With its rich Umpqua Valley farmland, the town quickly became an agricultural hotspot in the foothills of the Umpqua National Forest and Willamette National Forest. After the railroad came in 1865, Oakland became known as the turkey capital of the United States, and a vital connection between Portland and San Francisco. Today, the historic buildings and thriving community spirit remain.

“Our downtown is 2.5 blocks, and our blocks are short,” Keehley says. “But it’s a charming downtown.” There’s no stoplight, kids still play in the street and sirens and crowds are rare. The town is one of the beginning points of the Umpqua River Scenic Byway; biking is a great way to get around this blissfully slow-paced region.

Pick up a walking tour map at the Oakland Museum and take a self-guided tour of the historic homes and sites, including:

Stearn’s True Value Hardware Store, established in 1887 and still in operation today, by the same family.

The Oakland Tavern, established in 1898, is still serving up cold beers — along with sandwiches, bar snacks and a mean Bloody Mary.

It’s a bar, a cafe, a dance floor and an art gallery all in one. Oakland Art Gallery and Coco’s Cafe & Bar is a community hub, located in the old Turkey Hall, named in the 1930s because Oakland was famous for its Turkey Festival.

Triple Oak Vineyard’s Wine Vault tasting room is located in an old bank building, open weekends, focusing on small amounts of several varieties but especially its award-winning Tempranillo.

Oakland City Hall is a beautifully restored building, located in the old Washington School, built in 1910. In addition to city offices it includes the Oakland Public Library, preschool and and Community Center for meetings, parties and weddings.

The Oakland Museum, one of the biggest attractions, lets visitors step back in time with a walk through life as it was in the 1800s — everything from canning peaches at home to working in the livery stable, post office and forest as a logger.

With its marble-topped counter, old-fashioned ice cream parlor, candy counter, restaurant and antique-filled walls, the old Tolly’s Grill & Soda Fountain was an Oakland icon for 44 years until it closed recently. People still ask about it.

Come explore and appreciate Oakland’s historic buildings — more than 90 of them, built between 1852 and 1890.
In 1968 the Oakland Historic District was the first to be placed on the state’s historic register and is also on the National Historic Register.

Monthly events

Besides the walking tour, monthly events keep this community of 940 residents tight-knit.

March brings the annual St. Patrick’s Day Potato Bingo, complete with baked potato bar, bingo for the whole family and Irish songs by the Oakland Singers, of which Keehley is a founding member.

Spring brings the annual Oakland Car Show & Shine, when more than 100 classic cars cruise in for community music, food, antiques and family activities. There’s also the citywide garage sale, going on for 25 years now, and in June, the annual Melodrama performances by the Oakland Community Theater. This year it’s a Christmas play, which Keehley is directing.

No small town is complete without its own July 4th festivities. Oakland’s volunteer-run 4th of July Parade & Picnic in City Park is free and open to all, and typically draws an assortment of animals — horses, camels, chickens, dogs and cats — as well as classic cars, a bunch of kids, a barbecue (50-cent hot dogs and dollar-hamburgers), a water slide and bounce house.

About The

Jen Anderson
Jen Anderson writes and edits Travel Oregon's e-newsletters and other online content. She loves finding the latest places to eat, drink and play around the state with her husband and two young boys. Brewpubs, beaches and bike trails top the list.

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