Central Oregon’s Old School Charms

December 27, 2016 (Updated December 27, 2016)

The Beaver State’s old-school quirks have always gone straight to my heart. Things like spooning ice cream at a sticky diner, bellying up to the bar in a cowboy dive or wandering through a little museum full of bric-a-brac remind me — even after plenty of travel — why I’ve never been able to leave for long. Yes, even as Oregon grows up and gets more sophisticated, it hasn’t lost its laid-back charm. In fact, you’ll find a treasure trove of timeless attractions at the state’s center. Check out a few of these classic Central Oregon spots to see that shiny and new isn’t the only kind of cool.

Shaniko by Buddy Mays

Wander the streets of a ghost town

A team of residents keeps the antique buildings in Shaniko from falling into decrepitude in this ghost town northeast of Madras. Most ghosts are locked up in the winter, but it’s just as moody on a cold day to wander by the jail, saloon and schoolhouse in this former “Wool Capital of the World.”

Dig into a steak at classic cowboy restaurant

The Tumalo Feed Company is housed in a former general store built in 1910 and boasts an eclectic décor of cow skulls, red-checkered tablecloths and cowboy art. The drinks come in Mason jars and the menu looks like an old-time newspaper. Try the mountain oysters if you dare, or stick with the gigantic porterhouse steak, served with piles of sides delivered family style.

A.R. Bowman Museum by Robbie McClaran

Peruse Prineville’s past in a 1910-era bank

Step into this enormous former bank, built from brick in 1910, and wander through the history of Prineville, which is the oldest city in Central Oregon. Exhibits at A.R. Bowman Museum reveal historical challenges from fire to landowner disputes to what to do with all of those huge Ponderosa trees in the Ochoco Mountains (turn them into cash).

Horseshoe Tavern by Don Williams

Grab a beer at a quintessential dive bar

The Horseshoe Tavern in downtown Prineville once kept me entranced for an entire winter afternoon. The huge red horseshoe hanging out front drew me in, the classic Americana bar décor, jukebox, pool tables, friendly service and awesome people-watching kept me there. This is your spot to see a chandelier made out of a wagon wheel and lantern.

Oregon Trail of Dreams. Photo credit: Jay Mather

Glide through the snow on a dog-powered sled

For almost 40 years, Oregon Trail of Dreams has guided guests on sled dog rides on the flanks of Mt. Bachelor. Stay warm in the sled while a professional musher ferries you over the snow behind a sled dog team, with views of Broken Top and Three Sisters thrown in for good measure. It’s a classic winter adventure, no motors required.

Visit a stagecoach stop in the middle of nowhere

The 100-year-old destination Brothers Stage Stop was originally just what it is called, a stagecoach stop between Burns and Prineville. Today it operates as a restaurant, market, small store and post office, run by two sisters in Brothers. It’s about as rural and funky as it gets, with unpredictable hours and an eclectic clientele to prove it.

Go ghost hunting in Bend’s first school

I’ve been told a ghost named George inhabits the third floor of the Deschutes Historical Museum, but I’ve never encountered him. Maybe you’ll have better luck. In any case, in Bend’s first modern school, built in 1914 of locally quarried pink volcanic “tuff,” you can see the classroom of the school’s namesake teacher Mrs. Reid, logging artifacts, a 1907 Holsman car and many black and white photos of Bend in the early days.


Sno Cap Drive In by Mike Houska

Grab a cone at a classic ice cream diner

The Sno Cap Drive In in Sisters has been owned by the same family for nearly 40 years. It’s tiny but powerful, attracting lines of patrons outside waiting for a seat, or a meal handed through the take-out window. In winter, crowds thin, and it might be your best season for a spot at one of their famous booths — and the 38 flavors of ice cream taste just as good.

Pretend it’s the rodeo every day at a local’s favorite restaurant

At the Club Pioneer in Prineville, there is a wagon filled with horse tack, cowboy boots and American flags in the dining room. If that doesn’t delight you, the prime rib will. I suggest adding the mud pie and a shot of whiskey before wandering back outside to take in the big ol’ Wild West sky overhead.

Dine in Bend’s oldest restaurant with a view

The Pine Tavern restaurant hasn’t been around as long as Bend’s timber mills were, but it’s close. It was founded in 1936, and still pays a subtle homage to the lumber days with the enormous Ponderosa pine that grows through the center of its main dining room. The classic wooden tables and wood paneling are tried and true, and equally charming is the view of Mirror Pond, which has changed little in 100 years.

Club Pioneer

About The

Kim Cooper Findling
Kim Cooper Findling grew up on the Oregon Coast and became a Central Oregon girl in the mid-90s, taking in the sunny skies and never looking back (except a few wistful glances at the ocean). She is the managing editor of "Bend Magazine" and the author of “Bend, Oregon Daycations: Day Trips for Curious Travelers,” "Day Trips From Portland: Getaway Ideas for the Local Traveler” and “Chance of Sun: An Oregon Memoir.” Catch her around the state sampling microbrews, hiking river trails, walking beaches, and hanging out with her family. www.kimcooperfindling.com