Oregon Road Trip Itinerary: The Classic Loop Plus San Francisco to Oregon

Oregon packs almost every kind of Western scenery into one state: a rugged 360 mile coastline, the deepest lake in the country, high desert rock towers, glacier capped volcanoes, and a gorge lined with waterfalls. That is exactly why an Oregon road trip itinerary is one of the best drives in the American West, and why so many people build a San Francisco to Oregon road trip up the coast to reach it. This hub guide lays out the classic loop, the coast, and the redwood approach from California, tells you how many days you need, and points you to the best time to go. When you are ready to plan the hiking day by day, our detailed itineraries for the Crater Lake rim trail, the Oregon Coast Trail, and a Smith Rock weekend map out the trailheads and where to sleep.

The classic Oregon road trip loop

The heart of any Oregon road trip itinerary is a loop out of Portland that strings together the state's greatest hits. Drive it in either direction over 7 to 10 days and you will touch high desert, alpine lakes, volcanoes, and ocean, often in a single day of driving. Here is how the loop breaks down region by region.

1. The Columbia River Gorge and its waterfalls

Start just east of Portland in the Columbia River Gorge, where the Historic Columbia River Highway threads past a wall of waterfalls. Multnomah Falls is the headliner at 620 feet, and the short trails to Wahkeena, Latourell, and Horsetail Falls make an easy first day. For a longer hike, climb to the top of Multnomah Falls or out to Angel\'s Rest for a gorge overlook. The Gorge is green and misty in spring, which makes it a perfect warm up before you cross the Cascades into the sunnier high desert.

2. Bend, Smith Rock, and the high desert

Cross the mountains to Bend, the outdoor hub of central Oregon and the natural base for the eastern half of the loop. Half an hour north, Smith Rock State Park rises in a horseshoe of ochre cliffs above the Crooked River, and the Misery Ridge Trail delivers one of the best short, steep hikes in the state, with a payoff view of Monkey Face spire and the snow capped Cascades. Bend itself sits on the Deschutes River and puts the Cascade Lakes, lava fields, and dozens of trails within reach. Our Smith Rock weekend itinerary lays out the best two days here.

3. Crater Lake

From Bend, drive south to Crater Lake, the deepest lake in the United States and the single most striking sight in Oregon. A shattered volcano holds an impossibly blue pool ringed by cliffs, and the 33 mile Rim Drive circles the whole caldera with overlook after overlook. Hike the Watchman Peak trail for the classic view over Wizard Island, or drop down to the water on the Cleetwood Cove Trail, the only legal route to the lakeshore. Remember the Rim Drive is only fully open in summer and early fall. Our Crater Lake rim trail itinerary walks you through the best rim hikes and viewpoints.

4. The Three Sisters and the Cascade Lakes

Back near Bend, the Three Sisters Wilderness is the high country crown of the Cascades, three volcanic peaks over 10,000 feet ringed by alpine lakes, meadows, and lava flows. The Cascade Lakes Scenic Byway west of Bend is a gorgeous half day drive past Sparks Lake, Devils Lake, and Elk Lake with the peaks reflected in the water. If you have backpacking time to spare, this is where to spend it. Our Three Sisters Wilderness backpacking itinerary maps a multi day loop through the range.

5. The Highway 101 coast

Close the loop by dropping west to the Pacific and following Highway 101 north back toward Portland. The Oregon coast is a nonstop parade of sea stacks, headlands, and empty beaches: Bandon and Coos Bay in the south, the towering dunes of the Oregon Dunes National Recreation Area, the tide pools and lighthouses around Newport, and the iconic Haystack Rock at Cannon Beach near the northern end. Cap it at Ecola State Park and Astoria where the Columbia meets the sea. The Oregon Coast Trail itinerary breaks the best coastal walking into a five day plan.

San Francisco to Oregon road trip: the coastal approach

A San Francisco to Oregon road trip is the most scenic way to reach the state, trading the interstate for the wild Northern California and southern Oregon coast. Cross the Golden Gate Bridge and follow Highway 101 north. The whole coastal run to northern Oregon is roughly 600 miles, so give it at least 4 to 5 days.

Northern California redwoods

The first great stop north of the Bay is redwood country. The Avenue of the Giants near Humboldt winds for 31 miles through the tallest trees on Earth, and farther north Redwood National and State Parks protect groves like Tall Trees and the Lady Bird Johnson Grove, plus the elk meadows of Prairie Creek. Walk at least one grove trail, stand at the base of a 300 foot tree, and you will understand why this stretch is worth the extra days on a San Francisco to Oregon road trip.

Crossing into southern Oregon: Brookings, Gold Beach, and Bandon

Cross the state line near Brookings, where the Samuel H. Boardman State Scenic Corridor strings together the most dramatic sea stacks and hidden coves on the entire West Coast, Natural Bridges and Secret Beach among them. Keep north through Gold Beach at the mouth of the Rogue River, then Bandon, famous for its beach of standing rocks and the offshore Face Rock. This southern Oregon coast is quieter than the northern beaches and often skipped by loop travelers, which is exactly why the San Francisco approach is so rewarding.

Joining the classic loop

From the central Oregon coast you have two good options. Cut inland from Bandon or Coos Bay on Highway 42 or Highway 138 to reach Crater Lake and Bend and pick up the classic loop, or stay on Highway 101 all the way north through the Oregon Dunes, Newport, and Cannon Beach to finish near Astoria and Portland. Either way, a San Francisco to Oregon road trip folds neatly into the main itinerary above.

How many days do you need?

• 7 days: A tight classic loop from Portland, the Columbia River Gorge, Bend and Smith Rock, Crater Lake, and a taste of the coast, with short drives and a few key hikes.
• 10 days: The full loop at a relaxed pace, with the whole Highway 101 coast and a day in the Three Sisters or Cascade Lakes country.
• 12 to 14 days: A San Francisco to Oregon road trip that starts with the redwoods and the southern Oregon coast, then joins the classic loop for Crater Lake, Bend, and the northern beaches.

Best time to go

Late June through September is the best time for a full Oregon road trip itinerary, because the Crater Lake Rim Drive and the high Cascade trails around the Three Sisters are usually snow free and the coast is at its driest. July and August bring the most reliable mountain weather and the biggest crowds. September into early October is the sweet spot, with warm high desert days around Bend and Smith Rock, clear coastal skies, and thinner crowds. Spring and fall are lovely for the coast and the Columbia River Gorge waterfalls, but snow closes the Crater Lake rim and the higher Cascade passes outside of summer, so save the mountains for the warm months.

Plan your Oregon road trip

Ready to turn this hub into a day by day plan? Start with our Crater Lake rim trail itinerary for the centerpiece of the loop, add a Smith Rock weekend for the high desert, and follow the Oregon Coast Trail itinerary for the Highway 101 beaches. If you want to trade nights in town for nights under the peaks, the Three Sisters Wilderness backpacking itinerary shows you how to link the alpine lakes and volcanoes into a real backcountry loop.