Oregon is typecast as a land of conifer-smothered mountains dripping with rain. Those who know the Beaver State, however, know that the blue skies and rolling sage plains of Eastern Oregon could hardly be more unlike the soggy weather and soaring fir forests of the state’s western reaches. To really understand just how schizophrenic Oregon is, jump in your car and devote two days to the Portland-Bend Loop.
Start early (around 6 a.m.) and follow Interstate 84 east to Wood Village (Exit 16), then drive signed roads three miles south to Burnside Avenue, which is also Highway 26 East. Follow 26 east about 40 miles before turning left on Timberline Road. Drive six steep and winding miles to Timberline Lodge.
Walk around the historic lodge-a true American classic-and enjoy its singular setting and stonework. A memorable outing from this mountainside perch is to hike west on the Timberline Trail to Zig Zag Canyon (two miles) or Paradise Park (five miles). Alternately, rent ski gear, purchase a lift ticket ($39) and join national ski teams as they train above the lodge on Palmer Snowfield (summer hours: 7 a.m.-1:30 p.m.). Whether you hike or ski, bring a slopeside picnic.
Next, return to Highway 26 and follow it east to Madras, watching the forests morph from drenched fir groves to desiccated juniper stands. On the southern outskirts of Madras, merge with Highway 97 and drive south to Bend.
Bend, once a community of cowboy-hatted ranchers and loggers, is now a hub of Yuppies with kayaks, skis and bikes clamped to giant SUVs. Get a good overview of town by turning east on Highway 20 and driving a mile to a short trail that ascends to the dramatic viewpoint atop Pilot Butte. Spend the night at the Phoenix Inn (541-317-9292) if you’d prefer to stay in town, or at Widgi Creek (541-382-4449) for quieter digs on the outskirts of Bend.
For dinner, visit the Pine Tavern (try the Oregon Country Beef) or the Deschutes Brewery.Leave Bend on Day 2 after a Hobo-Scramble breakfast at the West Side Bakery and Café. Drive Highway 97 North to Terrebonne; then follow side roads to the towering walls of Smith Rock State Park. Walk down to the river, cross the bridge, and wander among the cliffs, rubbernecking at the international cast of climbers.
Back at Highway 97, continue north. Eventually you’ll merge onto Highway 197 North and descend into the Columbia River Gorge, where you’ll turn west on Interstate 84. The Gorge, with its cliffs and waterfalls, is a scenic wonder of the Pacific Northwest. Its strong, steady winds also make it a world-famous boardsailing center. At Hood River, visit Waterfront Park (Exit 63), and watch the windsurfers and kite-surfers work and play before visiting the downtown area for dinner at Andrew’s Pizza and Bakery.
Continue west on I-84 to Ainsworth State Park (Exit 35), and join the Historic Columbia River/Crown Point Highway. As you pass one waterfall after another, this historic route will challenge your film-rationing abilities. Reconnect with I-84 at Troutdale. As you drive the last few miles into Portland, take stock of how different the surroundings are now compared to those of the morning. Like we said, Oregon is one radically confused state.
LENGTH 405 miles
DRIVE TIME 8 hours
TRY TO AVOID Portland’s rush-hour traffic on both ends.
DON’T MISS McMenamins Edgefield Winery (800-669-8610) near Portland. Located off I-84 (Exit 16), it’s a Disneyland for ex-hippies, with a brewery, distillery, massage services, art shop and gardens.
GET OUT OF YOUR CAR at Crown Point along the Columbia Gorge Historic Highway for stunning views in all directions.
CONTACTS Mt. Hood Information Center (888-622-4822, mthood.info), Bend Visitors Center (800-949-6086, visitbend.org), Hood River Chamber (800-366-3530, hoodriver.org).