The Ideal 10-Day Oregon Summer Road Trip - Hexbag

The Ideal 10-Day Oregon Summer Road Trip


Oregon offers beaches, snow-capped mountains, deserts, volcanoes, waterfalls, and vineyards. The 10-day sample may cover everything

Oregon—a unique summer road trip destination!


Summer 10-day Oregon road trip
A road trip with my husband Elliot and a second Oregon Coast trip inspired this program. Recommended activities on this site are just mine!

-Road trip highlights:


Visit Portland, Willamette Valley wineries, Columbia Gorge hike/drive.
Viewing Mount Hood Bend, Painted Hills, Smith Rock State Park, and Crater Lake National Park.
Printable Oregon Coast road trip itinerary

Day 1: Portland arrival
Starting your Oregon road trip with a fly to Portland, its hippest city, is wonderful. Depending on your arrival time, explore downtown or Tom McCall Waterfront Park.

Parking costs may be avoided by hiring a vehicle until Day 3. Bike, walk, or take a cheap Uber to Portland. Not booked? Check automobile rental rates.

Bridge in Portland

My husband Elliot and I picked Hotel Rose – A Staypineapple Hotel, a block from Tom McCall Waterfront Park and walking distance to most downtown Portland attractions, for our first vacation. TripAdvisor reviews | Book now

The TripAdvisor-top-rated Hotel Lucia, Inn at Northrup Station, and The Benson Portland downtown are more Portland possibilities.

Our favorite Portland restaurants were Blue Star Donuts + Coffee (a excellent Voodoo alternative), Grassa (fresh pasta), and Bottle + Kitchen (at our hotel).

Day 2: Portland
Explore Portland now. Many unusual and intriguing things happen nowadays.

Wander Powell’s City of Books’ stacks, see the fragrant International Rose Test Garden (or the Portland Japanese Garden across the street), have lunch at one of Portland’s famed food cart pods (more open for midday than evening), and wait in line for a Voodoo Dough.

Drive time: Possible zero

I suggest Hotel Rose, Hotel Lucia, Inn at Northrup Station, and The Benson Portland in Portland.

Portland is the food truck capital—eat at a pod! The city has them everywhere.

Day 3: Willamette Valley
Oregon wine is acclaimed? It does! About 500 Willamette Valley Pinot Noir wineries.

Eugene is the greatest wine-growing area south of Portland, and Salem is an hour down I-5 a day trip from Portland.

Rent a vehicle and see Willamette Valley today. Popular vineyards include Eyrie, Domaine Drouhin, Elk Cove, Chehalem, Argyle, Sokol Blosser, Rex Hill, and Willamette Valley. Although few vineyards provide tours, most offer sampling.

Oregon Sokol Blosser Winery
Fodor’s Travel showed me a vineyard on a hill overlooking the countryside and a brilliant red home for our Oregon road trip. The picture didn’t depict this vineyard, which I wanted to visit!

I located the Sokol Blosser winery, one of the oldest and most renowned in the Willamette Valley, after an hour of Googling and visiting vineyard websites!

The guidebook was less appealing than wine and nibbles.

Oregon Sokol Blosser Winery
Driving time: 2–5 hours, wineries vary.

Willamette Valley lodging: Day 3 headquarters is in Portland. If you’d prefer change scenery, surrounding B&Bs are excellent. Visit Dundee’s La Bastide B&B.

Columbia River Gorge, Day 4
In September 2017, a West wildfire scorched the Gorge and neighboring woodlands. The enormous Eagle Creek Fire may restrict hiking trails and the Historic Columbia River Highway. Most locations are open, but check Forest Service website.

Oregon’s Columbia River Gorge
Day 4 of your Oregon road trip to the Columbia River Gorge involves hiking shoes and a camera. Over 80 miles of Columbia River canyon separate Washington and Oregon.

The Columbia River Highway, the first US scenic road, offers spectacular scenery and waterfalls. Take a couple short walks.

Multnomah Falls, Columbia Gorge
Most Columbia River Gorge tourists encounter Multnomah Falls, a 620-foot double cascade, but there are other beautiful sites.

Summertime Start early and be patient as highway traffic soon clogs vistas and trailhead parking!

Multnomah Falls, Columbia Gorge
Visit Latourell Falls, Oneonta Gorge, or Elowah Falls to get soaked.

In 2024, wildfires blocked Oneonta Gorge.

Many breaks, two hours.

Stay at Hood River or The Dalles, near Portland at the Columbia River Gorge’s end. The historic Hood River Hotel and Columbia Cliff Villas Hotel located in Hood River. Try Dalles Celilo Inn. Stay in Hood River for Day 5’s wonderful excursion.

Stay in Hood River on Day 4 and travel south on OR-35 to visit Mount Hood in the morning. Mount Hood, one of Oregon’s 7 Wonders, offers North America’s only year-round ski resort. Not enough time to ski, but nice landscape.

Go south to Bend, Oregon’s outdoor recreation capital. We visited Bend for our primary purpose, but every Oregon road trip should include this quaint town. Elliot’s sister lives there.

Pilot Butte, a town center extinct volcano, is a fantastic sunset viewpoint if clear.

Drive time: 3 hours

  • Sunset at Bend Sunset on Pilot Butte
  • Pilot Butte sunset, Bend
  • Sunset bend

TripAdvisor’s top Bend luxury hotel is Wall Street Suites. The affordable Hampton Inn & Suites Bend is well-rated. Downtown Oxford Hotel is active.

Bend’s Deschutes Brewery pub delivers fantastic meals and local beer. Bend has multiple breweries, Zydeco Kitchen & Cocktails provides Cajun/Creole Northwest cuisine, and Bar Rio serves Latin food.

Day 6: Bend
Bend and C/E Oregon have many sunny days. Hit one? Go outdoors today! Hire a bike, climb Pilot Butte, or “float the river” like a Bendita.

If the weather is awful (it was cloudy, damp, and chilly in Bend in June!), downtown Bend has several lovely stores and the High Desert Museum.

View of Pilot Butte Bend
Want to drive again today? The 66-mile Cascade Lakes Scenic Byway crosses Mt. Bachelor, Broken Top, South Sister, and 14 alpine lakes. Mount Bachelor provides picturesque chairlift excursions from the West Village base area to the Pine Marten Lodge at 7,775 feet in July.

The Cascade Lakes Scenic Byway takes 4-5 hours, although Mt. Bachelor takes an hour.

Visit McKay Cottage early on weekdays for Bend’s greatest breakfast. Otherwise, Bend Mountain Coffee is fantastic morning coffee. Pine Tavern, the city’s oldest restaurant, offers American.

Smith Rock, Painted Hills, Day 7
View Oregon attractions not on other road trip itineraries on Day 7. Morning starts 40 minutes northeast of Bend at Smith Rock State Park. Maybe the most gorgeous state park you’ve never heard of.

Smith Rock State Park
Smith Rock, “the birthplace of American sport climbing,” attracts climbers and hikers. Elliott and I trekked Misery Ridge for two hours, which was challenging but not horrible.

Crooked River hikes are simpler if a big trek doesn’t seem pleasant in the morning.

Leave Redmond for Eastern Oregon. Though ignored (Fodor’s has 38 pages on East Oregon), the trek is worth doing. Painted Hills of John Day Fossil Beds National Monument is near Mitchell, Oregon.

The Rainbow Mountain images from Peru that are everywhere online? Eastern Oregon is like that, except without the hard climb, height, and people!

Best taken in late afternoon and before sunset, the Painted Hills seem painted. The park has a picturesque drive and small hilltop treks.

Stay on the route and avoid hills while hiking here.

From Painthills Overlook and Paint Cove Trail, Bend is 2 hours away.

Total driving: 4.5 hours

Think about staying in Bend overnight. Stay at Sunriver Resort, 20 minutes south of Bend in the Cascade Mountains’ foothills, to spice things up and avoid leaving the Painted Hills too late. TripAdvisor reviews | Book now

Eastern Oregon: Day 8: Crater Lake
Start Day 8 early to view Crater Lake, Oregon’s most renowned national park! A full day may be had by leaving Bend/Sunriver early for Crater Lake National Park’s northern entrance.

Circle Crater Lake to the Steel Visitor Center for a lake film and park information from the north entrance. Drive counter-clockwise around Crater Lake or return to the visitor center to complete the 33-mile scenic circular drive*.

A two-hour park ranger-led boat excursion is Crater Lake’s most popular summer activity. Crater Lake Lodge offers tickets (worth visiting). The 700-foot-high 1.1-mile Cleetwood Cove Trail descends and ascends to the boat dock. This trail alone leads to the lake.

Besides the tough path, the lake features various lookouts and shorter excursions. Phantom Ship, Cloudclap Overlooks, Discovery Point. Easy/moderate treks include Castle Crest Wildflower Trail (excellent in July with wildflowers) and Watchman Peak Trail.

If it’s snowy, the Crater Lake route may open in early/mid-July. It generally opens from late June to early October. Summer road trips to Oregon in July or August provide the complete Crater Lake experience.

Real driving: 3–4 hours

Rooms at the exclusive Crater Lake Lodge sell out months (often a year) in advance. Stay at the Prospect Historic Hotel in Prospect, Oregon, or the Maple Leaf Motel in Shady Cove between Crater Lake and the coast tonight.

Day 9: Oregon Coast.
Today we’re going to the coast since no Oregon road trip is complete without viewing its magnificent coastline.

The Oregon coast
Prospect or Shady Cove may bring you to I-5 easily on Day 8. I would drive north to Sutherlin/Union Gap and west to the seashore.

This trail finishes in Reedsport, near Florence under the Oregon Dunes National Recreation Area. Explore the dunes before traveling north on 101.

In the afternoon, see Florence’s Sea Lion Caves, Yachats, and Newport’s Yaquina Head Lighthouse, Oregon’s tallest. I suggest stopping there tonight.

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