A Local’s Guide to Oregon Road Trip Destinations and Itineraries

There are so many great destinations to visit on an Oregon road trip. This is our list of top road trip destinations in Oregon, including the most popular destinations as well as a few off-the-beaten-path places with less crowds.

If you want to plan the perfect Oregon road trip itinerary, we hope our list of destinations, travel tips, and free road trip route itinerary guide will help.

I was born in Portland and have lived a majority of my life in Oregon’s Willamette Valley. This post includes some of my favorite places in Oregon to visit. But Oregon has so much to offer, there are still many more travel destinations in Oregon I still hope to explore!

The Best Time to Road Trip Oregon

I always say Oregon is the best place to be in Summer. Oregon’s Willamette Valley is lush, dry and warm from mid-June through September. Typically, it doesn’t get too hot. The weather is excellent, the land is green, and the sun sets late in the evening, making Summer an ideal time for exploring.

Spring and Fall can also be pleasant in Oregon, though the chance of rain increases. Be sure to pack a rain coat, just in case. And make a back-up plan for activities that may be hampered by inclement weather. Crowds in tourist areas also go down while school is in session.

November through February can be pretty dreary and wet on the West side of Oregon. Fortunately, temperatures rarely drop below freezing in the Valley, but outdoor activities can be pretty miserable in cold rain nonetheless. Oregon is great for outdoor snow sports in places like the Cascade Mountain Range and Central Oregon, where the skies remain clear more often.

Oregon Road Trip Destination Map

Top Oregon Road Trip Destinations

1. The Oregon Coast

The Oregon Coast has countless destinations to visit from North to South. Oregon’s coastal towns are known for great seafood, sandy beaches and vibrant tidepools, plenty of scenic viewpoints, and shops full of special treats like fudge and salt-water taffy.

Fair warning: Oregon’s sea water is cold year-round, but some people do surf (usually with wet suits) in places like Pacific City. While the Northern Oregon Coast, like Lincoln City, tends to have more long stretches of beach, the Southern Coast boasts striking cliffs and unique rock formations that are out of this world.

You can easily get to the Oregon Coast on a day trip from Portland or other cities off of Interstate 5. Driving down the whole coast via Highway 101 can also be done in a day (7.5 hours without stops). 

Good for: Scenery, hikes, seafood, beaches, scenic drives
Time to spend: 1 day to 2 weeks
Where to stay: Neskowin or Lincoln City vacation rentals, Looking Glass Inn (Lincoln City), Florence rentals, Samuel H. Boardman Scenic Corridor vacation rentals, Beachfront Inn (Brookings)

2. Crater Lake National Park

Crater Lake is Oregon’s one and only National Park. (To be honest, we find Oregon’s State Parks to be just as remarkable, if not more.) It’s a bit “in the middle of nowhere”, located just South of what we call Central Oregon.

Crater Lake has formed within a collapsed volcano. There are trails with great viewpoints surrounding the lake as well as leading down to its deep, cerulean waters. 

Good for: Scenery, hikes
Time to spend: 1 or 2 days
Where to stay: Fort Klamath guest house, Crater Lake Lodge or cabins, Sleep Inn & Suites (Chiloquin)

3. The Columbia River Gorge and Multnomah Falls

The Columbia River is a massive waterway on the border of Oregon and Washington. The Columbia River Gorge is a National Scenic Area with incredible vistas from the historic highway. Waterfalls and hikes are abundant in this area.

Perhaps Oregon’s most visited, photogenic destination is Multnomah Falls. It can be seen from Highway 84 or you can get up close and personal on a one mile out-and-back hike to the top. This Oregon landmark can become quite crowded. Don’t miss the other waterfalls along the historic highway, too.

Note that some areas of the Gorge have been impacted by forest fires in recent years, so be sure to check what is open before visiting.

Good for: Scenery, hikes, waterfalls, windsurfing and water sports, scenic drives
Time to spend: 2 days – 1 week
Where to stay: Hood River vacation rentals, Best Western Plus Hood River, Columbia Gorge Hotel & Spa

4. Mt. Hood and the Cascades

By Oregon’s Mt. Hood Territory. – Public Domain, Link

Mt. Hood is Oregon’s highest mountain and an Oregon icon, often visible from Portland. It is home to six ski areas and the Historic Timberline Lodge, which was constructed as part of the WPA during the Great Depression.

The epic Pacific Crest Trail passes by Mount Hood and continues down the Cascade Range by Three Sisters, Mt. Washington, and Mt. Jefferson. 

Note that the mountain passes do get more snow than other parts of the State, so be prepared with snow tires or chains when driving in Winter.

Good for: Scenery, hiking, snow sports, fishing
Time to spend: 1 day to 1 week
Where to stay: Historic Timberline Lodge, Mt. Hood Vacation rentals

5. Willamette Valley: Oregon Wine Country

Oregon’s green and gorgeous Willamette Valley is home to a blossoming wine country as well as historic hops farms. You can visit cute, small towns like Independence, McMinnville, and Amity. Or stay rural, driving through bountiful landscapes full of vineyards and farmland on the rolling hills.

While Oregon wine country is a popular destination, it is by no means over-run. This area is enjoyed by visitors and locals alike, especially June through September.

Good for: Scenery, beer and wine tasting, cycling, farm-to-table food
Time to spend: 1 day to 1 week
Where to stay: Independence Hotel, Yamhill County vacation rentals, Bella Collina Bed & Breakfast (Amity)

Read next: Monmouth & Independence Oregon Visitors Guide | Top Day Trips from Salem | Hidden Gems in the Mid-Willamette Valley 

6. Portland, Oregon

The city of Portland has become a booming Oregon travel destination in the past decade. Known for its quirky, creative, environmentally-friendly culture, there’s plenty to do for every interest. Personally, we prefer exploring Portland’s neighborhood districts over the downtown. But you’ll find excellent restaurants and food carts no matter where you go.

Portland’s parks, International Rose Garden, urban hikes, and Springwater Corridor trail are also worth mentioning. If you’re flying into PDX airport, Portland makes an easy starting point for just about any Oregon road trip itinerary.

Good for: Parks, restaurants, shopping, events
Time to spend: 2 – 4 days
Where to stay: Portland rentals, McMenamin’s Kennedy School, Hotel Monaco or The Duniway Hotel (downtown)

Read next: A Local’s Guide to Portland

* Access our free Portland packing checklist here *

7. Central Oregon

East of the Cascade Mountains is the wide open high desert known as Central Oregon. Its dry, sunny climate makes Central Oregon a paradise for outdoor adventure all year round. You can float the Deschutes River in an inner tube on a hot day or shred the nearby ski slopes in winter. This is why many visitors take vacations here, whether at a guest house rental or self-catering resort. 

In addition to outdoor adventures like hiking, biking, kayaking, rock climbing, and more, the city of Bend offers plenty of shopping and dining. Smaller towns like Sisters, Redmond, and Tumalo also have cute shops and cafes to try.

Good for: Scenery, hiking, snow sports, water sports, resorts
Time to spend: 2 days to 1 week
Where to stay: Sisters, OR vacation rentals, SpringHill Suites by Marriott (Bend), Sunriver Resort, Brasada Ranch

Read next: How to Choose the Best Central Oregon Resort for Your Vacation

8. Silver Falls State Park

While Silver Falls gets its fair share of visitors, I’m often surprised how few Oregonians have heard of this epic State Park. Located an hour East of Oregon’s capital city, Salem, the park boasts 9 majestic waterfalls on a single day hike. What’s more, hikers can walk behind two of those falls!

If you only visit one natural wonder on your Oregon road trip, let this be it. You can stay on site at the campground or find lodging in the quaint town of Silverton nearby. Abiqua Falls is another nice hike not too far away.

Good for: Hiking, waterfalls
Time to spend: 1 or 2 days
Where to stay:  Oregon Garden Resort (Silverton), Salem hotels and vacation rentals

Read next: Oregon’s Best Kept Secret: Silver Falls State Park | Best Breakfast in Salem Oregon: Guide to Salem Breakfast Restaurants

Off the Beaten Path Oregon Road Trip Destinations

9. Klamath Falls

Known as the “City of Sunshine”, Klamath Falls is at the Southern point of Klamath Lake, not too far from Crater Lake as well as the border of California. There isn’t much in the way of waterfalls here, despite the name. It’s mostly prairie lands. A big draw is four famous golf courses and a couple of resorts.

Good for: Resorts, golfing
Time to spend: 2 days to 1 week
Where to stay: Running Y Ranch Resort, Klamath Falls vacation rentals

10. John Day Fossil Beds & Painted Hills

The John Day area is a geology-lover’s paradise, located in the desert plateau of Eastern Oregon. With fossils as old as 95 million years, all kinds of prehistoric plants and animals have been found, preserved in the area’s ancient mud flows. The multi-colored Painted Hills are home to accessible, scenic trails as well as miles of scenic bikeways.

Good for: Scenery, cycling, geology, paleontology
Time to spend: 2 – 4 days
Where to stay: John Day vacation rentals, Clyde Holliday State Recreation Site

11. Umpqua National Forest and Waterfalls

In Southwest Oregon, not far from Crater Lake, is the Rogue-Umpqua National Scenic Byway (Highway 138). The area has over 50 campgrounds, countless trails through fir forests, and stunning waterfalls. Toketee and Watson Falls are two of Oregon’s hidden gems. Diamond Lake provides boating as well as fishing opportunities (even in winter).

Good for: Scenery, hikes, waterfalls, fishing, camping
Time to spend: 1 – 4 days
Where to stay: Toketee Lake campground

12. Steens Mountain Wilderness

In Oregon’s remote Southeastern corner is one of Oregon’s most rugged and least-visited destinations: the Steens Mountain Wilderness. Find solitude in backcountry camping, relax in some hot springs, or take a scenic drive to the Alvord Desert, where the landscape makes you feel like you’re on another planet.

Good for: Scenery, backpacking
Time to spend: 2 – 4 days
Where to stay: Burns, OR vacation rentals, Steens Mountain Wilderness Resort

13. The Wallowas

In the corner of Northeast Oregon is the remote Eagle Cap Wilderness and Wallowa Mountains. This area is called “Little Switzerland” for its scenic peaks and alpine lakes. It was the original homeland of the Nez Perce tribe.

The main town of Joseph, Oregon has cute shops, art, and museums. Further afield, take a self-guided tour to view the area’s beautiful barns. 

Good for: Scenery, outdoor adventures, nature, history
Time to spend: 2 days to 1 week
Where to stay: Wallowa Lake vacation rentals, Eagle Cap Chalets (Joseph)

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Our Top 5 Oregon Road Trip Itinerary Ideas

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