Great Oregon Itineraries


Great Oregon Itineraries

Best of Oregon Tour

The Plan

DISTANCE: 1,060 mi

TIME: 10 days

BREAKS: Overnight in Portland, Cannon Beach, Florence, Eugene, Ashland, Crater Lake, Bend, Hood River

Days 1 and 2: Portland

Start by spending a couple of days in the state's largest city, where you can tour the museums and attractions that make up Washington Park, as well as the Lan Su Chinese Garden in Old Town, and the excellent museums and cultural institutions along downtown's leafy Park Blocks. This city of vibrant, distinctive neighborhoods offers plenty of great urban exploring, with Nob Hill, Hawthorne, and the Mississippi Avenue Arts District among the best areas for shopping, café hopping, and people-watching. If you have a little extra time, consider spending a couple of hours just south of the city in the Willamette Valley wine country—it's an easy jaunt from Portland.

Days 3 and 4: The Coast

Leave Portland early on Day 3 for the drive west about 100 mi on U.S. 30 to the small city of Astoria, which has several excellent spots for lunch and the Columbia River Maritime Museum. Pick the main scenic highway down the Oregon coast, U.S. 101, and continue south stopping at Fort Stevens State Park and the Fort Clatsop National Memorial. In bustling Seaside, stroll through the touristy but lively downtown before ending the day in charming Cannon Beach (26 mi south of Astoria), which has a wealth of oceanfront hotels and inns, many with views of one of the region's seminal features, 235-foot-tall Haystack Rock.

The following morning, continue south down U.S. 101. In Tillamook (famous for its cheese), take a detour onto the Three Capes Loop, a stunning 35-mi byway. Stop in small and scenic Pacific City (at the south end of the loop) for lunch. Once you're back on U.S. 101, continue south to Newport, spending some time at the excellent Oregon Coast Aquarium as well as Oregon State University's fascinating Hatfield Marine Science Center. Your final stop is the charming village of Florence, 160 mi (four to six hours) from Cannon Beach.

Day 5: Eugene

Spend the morning driving 20 mi south of Florence along U.S. 101 to scamper about the sandy bluffs at Oregon Dunes National Recreation Area near Reedsport. Then backtrack to Florence for lunch in Old Town before taking Highway 126 east for 60 mi to the attractive college city of Eugene, staying at one of the charming inns or bed-and-breakfasts near the leafy campus of the University of Oregon. Take a walk to the summit of Skinner Butte, which affords fine views of the city, and plan to have dinner at one of the excellent restaurants at the 5th Street Public Market. Budget some additional time in Eugene the following morning to visit two excellent University of Oregon museums, the Jordan Schnitzer Museum of Art and the Oregon Museum of Natural History.

Days 6 and 7: Ashland and Crater Lake

From Eugene, take Interstate 5 south for 60 mi to historic Oakland, where a delicious lunch awaits at Tolly's Restaurant and Soda Fountain. If you're visiting in summer, continue 15 mi down Interstate 5 to Roseburg, and then head east along Highway 138 (the Umpqua River Scenic Byway), which twists and turns over the Cascade Range for 85 mi to the northern entrance of Crater Lake National Park. Once inside the park, you can continue along Rim Drive for another half hour for excellent views of the lake. Overnight in the park or in nearby Prospect.

The following morning, take the lake boat tour to Wizard Island and hike through the surrounding forest. In the afternoon, head southwest on Highway 62 to Interstate 5, and then on to Ashland, 95 mi (about two hours) from Crater Lake. Plan to stay the night in one of Ashland's many superb bed-and-breakfasts. Have dinner and attend one of the Oregon Shakespeare Festival productions (mid-February through early November). If it's winter and Crater Lake's roads are impassable, from Oakland (above) continue straight down Interstate 5, stopping to check out the towns of Grants Pass and Medford, and end Day 6 in Ashland (125 mi south of Oakland), where you can spend two evenings.

Days 8 and 9: Bend

Get an early start out of Ashland, driving east along scenic Highway 66 for 60 mi to Klamath Falls, where you can stop for lunch and to tour the excellent Favell Museum of Western Art and Native American Artifacts, and the extensive Klamath County Museum. Then drive north on U.S. 97, stopping if you have time at Collier Memorial State Park, to reach the outdoorsy resort town of Bend, where you can spend two nights checking out the parks, mountain hikes, microbreweries, and hip restaurants of the state's largest city east of the Cascades. Be sure to visit the outstanding High Desert Museum, the Old Mill District, and Mt. Bachelor Ski Area (which has outdoor activities year-round).

Day 10: Hood River

From Bend, continue north up U.S. 97, and then northwest up U.S. 26 to Mt. Hood, 105 mi total. Have lunch at the historic Timberline Lodge, admiring the stunning views south down the Cascade Range. Pick up Highway 35 and drive around the east side of Mt. Hood and then north 40 mi up to the dapper town of Hood River, in the heart of the picturesque Columbia Gorge. Spend the night at one of the attractive inns, and try one of this town's stellar restaurants for dinner. From here it's just a 60-mi drive west along a scenic stretch of Interstate 84 to reach Portland, or you could drive east through the gorge through The Dalles and on to the Wild West town of Pendleton, 150 mi east.The town's regional airport connects to Portland and Seattle.


For a fuller sense of the Oregon Coast, continue down to Bandon and eventually all the way to Brookings on Day 4, where you can spend the night. Then on Day 5, continue south to Crescent City, California, and pick up U.S. 199 northeast to Grants Pass, where you can continue on to Ashland and Crater Lake. From U.S. 199, note that Oregon Caves National Monument makes for an interesting detour. Allow an extra day or two if you go this route.

From Bend you could easily add two additional days to your trip by making a loop drive through eastern Oregon. Follow U.S. 26 east to Ochoco National Forest, John Day, and—via Highway 7—historic Baker City, 230 mi total. From here it's a 240-mi drive west on Interstate 84 to Hood River via Pendleton and the scenic Columbia Gorge.

Five Scenic Oregon Drives

Cascades Lakes Scenic Byway

2 to 4 Hours

This mountainous 66-mi tour, which is closed in winter due to snow, passes shimmering mountain lakes and prime geological examples of how glaciers and volcanoes have contributed to Oregon's rugged landscape. The route begins just west of Bend on Forest Road 46, which climbs up into the Cascades and through the towering evergreens of Deschutes National Forest before turning south by Devil's Lake. The road ends at Highway 58, about 80 mi southeast of Eugene.

The High Desert: Bend to Baker City

5 to 8 Hours

This 230-mi drive from Bend across the state's consistently sunny high desert is popular year-round for its stunning big-sky panoramas. Follow U.S. 97 north to Redmond (from which you could easily detour to Cline Falls State Park for a picnic, or up to the rugged hiking of Smith Rock State Park). Next turn east on U.S. 26 and follow the road through verdant ranch lands around Prineville and into the pine-forested ridges of Ochoco National Forest. Continue into eastern Oregon through the Painted Hills unit of John Day Fossil Beds National Monument, with its fascinating geological formations, and on through such historic gold-mining centers as John Day, and—via scenic U.S. 26 and Highway 7—Baker City.

Historic Columbia River Highway

1 to 3 Hours

Several spans still exist of this 75-mi road through the magnificent Columbia Gorge. The Historic Columbia River Highway (U.S. 30) opened in 1922 and is considered a masterful feat of highway engineering, as it climbs over verdant riverside bluffs and passes beside several massive waterfalls. The longest continuous stretch of road extends from Troutdale, just east of Portland, and climbs and dips for 22 mi parallel to the Columbia River, ending just west of Bonneville Dam. Be sure to stop at Crown Point State Scenic Corridor, with its 30-mi views up and down the gorge.

The Southern Coast: U.S. 101 from Brookings to Florence

4 to 6 Hours

You'll spy some of the most majestic maritime scenery in the West on the stretch of U.S. 101 that extends north from the Oregon/California border for 160 mi to Florence. You'll first arrive in the pretty fishing village of Brookings, through panoramic views from Samuel H. Boardman State Park, quaint Port Orford, and Oregon Dunes National Recreation Area in Reedsport. Finish just north in picturesque Florence, which lies on the Siuslaw River and has a charming Old Town with several fine restaurants.

Washington County's Vineyard and Valley Scenic Tour

3 to 6 Hours

This meandering series of country roads passes through the heart of Washington County, the nearest patch of the Willamette wine country to Portland, which makes it perfect for an afternoon drive—interspersed with some first-rate wine tasting. The 50-mi route ( begins just off U.S. 26, Exit 61, in Swiss-settled Helvetia, turns south through Forest Grove's pastoral wine country, and then finishes with a turn through the fertile Tualatin Valley, passing by vintage general stores and historic taverns.

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