East Wind Drive-In

No matter how devoted, every foodie needs a break once in a while—a moment to give that precious palate a chance to recalibrate. Our prescription? A food-filled jaunt along Oregon’s loveliest stretch of pavement: the Historic Columbia River Highway. Use our map to tailor your own old-school adventure—with a generous side of kitsch.

Pit Stops

Sandy River Delta Park

One of the highway’s best riverside picnic spots is also Oregon’s largest off-leash dog park: more than 1,400 acres of meandering wilderness trails through restored forest and wetland. There’s no drinking water on site, so pack your Nalgene. I-84 exit 18, Crown Point Highway, Troutdale

Tad's Chicken 'n Dumplins

Tad’s Chicken ’n Dumplins

This rustic mainstay has served gravy-doused stewed chicken with fist-size dumplings from its idyllic perch over the Sandy River since the 1920s. Don’t leave without striking a pose beneath the eatery’s classic neon sign. 1325 E Historic Columbia River Hwy, Troutdale; tadschicdump.com

Shirley’s Tippy Canoe

Once a free-for-all watering hole for motorcyclists, the Tippy Canoe was purchased by namesake Shirley Welton in 2005 and reimagined as an inviting country roadhouse. Drop in for behemoth portions of Sloppy Joes, French dips, and steaming fish and chips. 28242 E Historic Columbia River Hwy, Troutdale; shirleysfood.com

Corbett Country Market

One part gas station, one part down-home deli, and one part museum, this charming pit stop serves up barbecue sandwiches, house-smoked salmon and jerky, home-style lasagna, and 17 microbrews alongside a vintage clothes-iron collection from the Crown Point Historical Society. 36801 E Historic Columbia River Hwy, Corbett; 503-695-2234

Multnomah Lodge

MULTNOMAH FALLS LODGE

The 620-foot, double-tiered cascade ranks with Powell’s and the International Rose Test Garden as a rite of passage for tourists and newcomers—but few locals ever venture into the lodge. Take our advice and treat yourself to the dining room’s unparalleled views, gooey house-made cinnamon rolls topped with Oregon hazelnuts, and a mug of Hood River Coffee. E Historic Columbia River Hwy, Bridal Veil; multnomahfallslodge.com

EAST WIND DRIVE-IN

Just a few blocks from the aptly named Bridge of the Gods, this retro roadside walk-up specializes in springy curly fries, no-frills burgers, and seriously supersized soft-serve cones. Good luck managing the $2 “small,” towering precariously at more than eight inches tall. 395 NW Wa Na Pa St, Cascade Locks; 541-374-8380

Bette's Place in Hood River

BETTE’S PLACE

No collection of comfort food would be complete without a greasy spoon, where you’re treated like a long-lost cousin and breakfast is served all day. Head to the legendary Bette’s for an afternoon snack: omelets brimming with fresh Dungeness crab, airy cinnamon buns, and a no-nonsense staff that hasn’t changed much since 1975. 416 Oak St, Hood River; bettesplace.com

MCMENAMINS EDGEFIELD

Stroll off this epic day of eats wandering lush gardens, or sneak in a sunset round of pitch and putt at one of two par-3 golf courses that wind through this sprawling historic site, built as the county poor farm in 1911. 2126 SW Halsey St, Troutdale; mcmenamins.com/edgefield

Photo Ops

Vista House at Crown Point

• Portland Women’s Forum State Scenic Viewpoint

• VISTA HOUSE AT CROWN POINT

• SHEPPERD’S DELL

• BRIDAL VEIL FALLS

• Oneonta Gorge

• Horsetail Falls

Road to the Past

The rise, fall, and rebirth of America’s first scenic highway

Engineered to give motorists access to the rugged beauty of the Columbia River Gorge without disrupting the natural landscape, the cliff-clinging, 75-mile Columbia River Highway was a marvel of early highway design. Ground broke on Oregon’s “King of Roads” in 1913, manifesting architect Samuel C. Lancaster’s vision, inspired by the famed Axenstrasse route in Switzerland. Unfortunately, the highway’s popularity resulted in early aging: waterfall-spanning bridges buckled, tunnels filled with rock, and by the time the Bonneville Dam opened in 1937, many stretches were abandoned in favor of the faster, water-level route that would become I-84. Surveys from the National Park Service and recognition from the National Register of Historic Places prompted a renewed drive in the 1980s to repair of miles of bridges, stone markers, and scenic stops. The effort to transform additional stretches of the road into the Historic Columbia River Highway State Trail for hikers and bikers continues today.

Hit The Road

Pack: A camera worthy of the Gorge’s sweeping views, lichen-draped waterfalls, and roadside moments

Hot tip: Two-wheel it! More than 10 miles of the road are now off-limits to cars and motorcycles. 

Soudtrack: Woody Guthrie’s Columbia River Collection, with regional odes like “Roll On, Columbia” and “Pastures of Plenty”

This article appeared in the September 2013 issue of Portland Monthly Magazine.

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