10-Day Best of Oregon Road Trip Itinerary

It’s almost impossible to cover all of Oregon in a week, so we’ve crafted a 10-day tour that hits most of the highlights. Although we think it would be a great trip, don’t take this itinerary too seriously—and don’t hesitate to stay longer at one site or discover your own favorite places along this route. With a mere 10 days to explore the entire state in this itinerary, we couldn’t quite get you into the heart of eastern Oregon, but that doesn’t mean we don’t highly recommend this part of the state. In fact, we like it so much we’ve devoted an entirely different itinerary to it.

A tree blossoms in the foreground while across the water is a view of the cityscape.

Springtime in Portland. Photo © Gino Rigucci.

Day 1


Fly into Portland International Airport and either pick up a rental car or take the MAX light rail train into town and arrange to get a rental car in downtown Portland. Spend the afternoon strolling around downtown, visiting Powell’s Books and the Pearl District. Spend the night at the Heathman Hotel and dine nearby at old fave Higgins Restaurant & Bar or, a slightly longer walk away, at Tasty n Alder.

Map of Portland, Oregon


Day 2

North Coast

Head northwest out of Portland on U.S. 30 to Astoria. Explore this historic town at the mouth of the Columbia River, including a visit to the replica of Fort Clatsop, which served as Lewis and Clark’s winter home in 1805-1806. Then continue south and spend the night in Cannon Beach at the Stephanie Inn.

Day 3

North Coast to Central Coast

Head south out of town on U.S. 101 and stop for a walk at Oswald West State Park, where you can follow a short trail through an old-growth forest to Short Sands Beach to watch the surfers. Then drive down the coast as far as Yachats and spend the night at Overleaf Lodge. Eat dinner and catch some live music at the Drift Inn.

Day 4

Central Coast to the Willamette Valley

Spend the morning exploring the tide pools and old-growth forest around Cape Perpetua. Take a tour of Sea Lion Caves (or just peer down from the road with your binoculars). From the seaside town of Florence, cut east on Route 126 to Eugene, with a detour south to Lorane for a visit to the King Estate Winery tasting room. Spend the night near Eugene’s riverside trails at the elegant Inn at the 5th.

The view from atop Cape Perpetua. Photo © W.C. McRae.

The view from atop Cape Perpetua. Photo © W.C. McRae.

Day 5-6

Ashland and Southern Oregon

Drive south along I-5 to Ashland to attend a world-class play. Dine at New Sammy’s Cowboy Diner (reserve well in advance) or Amuse, and spend the night at the Ashland Springs Hotel.

From Medford, just north of Ashland, drive up the Rogue River on Route 62 through the tiny towns of Prospect and Union Creek to Crater Lake National Park, where you’ll spend the night at the Crater Lake Lodge.

Map of Crater Lake National Park, Oregon

Crater Lake National Park

Day 7

Bend and Central Oregon

Head north on U.S. 97 to Bend, visiting the Lava Lands Visitor Center and High Desert Museum on the way. Stay downtown at the Oxford Hotel or a few miles out of town along the Deschutes River at the Mount Bachelor Resort.

Day 8

Central Oregon to Mount Hood

Continue north to Maupin to meet your raft guide for a daylong float down the Deschutes. At the end of the day, drive up Mount Hood and spend the night at Timberline Lodge.

Portland, Oregon and Mount Hood.

Portland, Oregon and Mount Hood. Photo © Piotr Zajda /123rf.

Day 9

Columbia River Gorge and Mount Hood

Hike along the Timberline Trail (or spend the morning skiing—even in August) and then drive to Hood River. Take a hike to Upper Horsetail Falls and then continue west to Troutdale, where you’ll spend your final night at McMenamins’ Edgefield.

Map of the Columbia River Gorge and Mount Hood in Oregon

Columbia River Gorge and Mount Hood

Day 10

Return to Portland

It doesn’t take long—about 20 minutes—to get from Edgefield to the Portland airport. If you have a late flight, spend the day in Portland, visiting Washington and Forest Parks.

Excerpted from the eleventh Edition of Moon Oregon.

Leave a Reply

Your email address will not be published. Required fields are marked *