10+ of the Best Oregon Road Trips You Cannot Miss

Oregon, famous for being the destination of the Oregon Trail, contains many amazing road trip opportunities. With tons of outdoor and hiking opportunities, Oregon also offers amazing wine, beer, and food. Also home to the world’s largest cheese factory, the shortest river ever, and the deepest lake in the United States, you can never go wrong with a trip to Oregon. Plan your trip to Oregon and check out some of the best Oregon Road trips below.

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The Best Oregon Road Trips from Portland

Portland to the John Day Fossil Beds Loop

By Lisa Marquardt of The Hot Flash Packer 

For one of the best Oregon road trips, head out to the John Day Fossil Beds National Monument. This park contains 3 distinct units, with other things to do along the way. You can do this trip from Portland or Bend/US Highway 97. Your first stop is the ghost town of Shaniko. Check out the old jail and hotel. You will drive along highway 218 and your next stop is the Clarno Unit. Here you can see fossils of trees in the rocks and cliffs.  

In the town of Fossil, you can search for your own fossils near the high school. Drive on highway 19 to your next stop, a hike in the Blue Basin Overlook Trail. After your hike, stop at the John Day Fossil Beds visitor center to see the laboratory and casts of actual fossils found in the area.  You can also visit the historic ranch overlooking Sheep Rock.

Next, head west on US Highway 26, to the Painted Hills Unit, the highlight of John Day Fossil Beds. Here you can walk among the colorful clay hills, with colors of browns, blacks, yellows, and reds. If you have the energy and time, head over to Smith Rock State Park and hike one of the fantastic trails, such as Misery Ridge. It will take at least two full days to complete the 300-mile loop to Shaniko.

Portland to Seattle

By Agnes of The Van Escape

An excellent idea for a weekend getaway from Portland is a road trip to Seattle through the amazing Mount Rainier National Park. Start your trip on a Friday afternoon to catch the sunset in Mt Rainier. The road from Portland to Mt Rainier via the I-5 N is 138 miles long, so it will take you approximately 2 hours and 30 minutes. After sunset stay overnight in Longmire or Ashford, both a few miles from the park.

The next morning, start exploring Mount Rainier National Park. The park was established in 1899 as the fifth national park in the United States. Mount Rainier is a 14,411-foot (4,392 m) stratovolcano. Furthermore, there are 25 glaciers around the park, amazing lakes, and waterfalls.

The park includes a vast old forest and many mountain meadows. Follow a driving tour to see the most stunning vistas. Stop at the Reflection Lake which offers the most spectacular reflection of a sleeping volcano in the water.

The best way to explore the park and admire its wildlife is to go on a hike. You have many hiking trails to choose from. One of the most beautiful is the Pinnacle Peak Trail, which starts at the Reflection Lake. It is a moderate hike, which takes you about three hours both ways. A description of this hike and more attractions in the park you will find in the post things to do in Mount Rainier National Park.

From Mt. Rainier to Seattle, the most scenic route is via WA-410 W and I-90 W, which is 95 miles, and it will take two hours. In Seattle, it is worth spending a day or two to see the most exciting attractions in the city, such as the Space Needle, the Chihuly Gardens, or Pikes Place Market.

Portland to Bend

By Lindsey Messenger of Seven Day Weekender

Bend is one of those small cities that makes a great weekend road trip from Portland and one of the best Oregon road trips. The quickest direct route to Bend is about 3 hours. However, a more fun way to get to this outdoor lovers paradise is the scenic route through the Willamette Valley and Sisters.

This 195-mile trip takes about 4 hours. Although the trip from Portland to Bend is very doable in one day it is more enjoyable to spend the night in wine country. This is a road trip you must experience due to its ability to give you a unique view of what Oregon does best: wine, quirky activities, and outdoor adventure.

Willamette Valley

Begin your journey slightly SW of Portland in the Willamette Valley. There are more than 1,300 wineries and vineyards spread throughout the Willamette Valley, and it is one of the best wine regions in the United States. A visit to Adelsheim, Durant Vineyards, and Alloro Vineyard are highly recommended.

Coupled with the multitude of cute little towns and the Evergreen Aviation & Space Museum in McMinnville (which houses the famous Spruce Goose that Howard Hughes flew), you will have more than enough to see by making this an overnight stop on your road trip.

When choosing a place to stay in the Willamette Valley make sure it’s a memorable one: a vintage airstream at The Vintages Trailer Resort. Depending on how early you head out the next day there are one or two more places you should stop before arriving in Bend. Bend also has many things to see and do.

Silver Falls State Park and Sisters

Hiking is as synonymous with Oregon as the beach is with California. Thus, stop in Silver Falls State Park to walk along their 9-mile loop trail and check out one of the 10 beautiful waterfalls scattered throughout the park. From there hop back on the highway and make your final stop in the town of Sisters.

Sisters is well worth the stop because of the fact as soon as you drive into the town you feel as though you have stepped onto a movie set of a Western film, or the HBO show Westworld. If you love quilting or quirky small downs this is the spot! For a unique place to share on your social media, look no further than Sisters. When you are ready to leave Sisters the good thing is Bend is only 30 minutes away.

Bend

After arriving in Bend, if there is one place you must see it would be Smith Rock State Park. The park covers over 650 acres across the high desert where you can indulge in horseback riding, hiking, rock climbing, and many other outdoor activities.

The dog-friendly park is open year-round and is the perfect morning activity before the heat of the day. With a day-use fee of $5, it is the perfect budget activity, and one of the most memorable activities to do in your final destination.

The Best Oregon Road Trips to Take Within Oregon

Medford to Eugene 

By Monica Lynn of This Rare Earth

The Umpqua National Forest is one of the most scenic areas in Oregon and makes for one of the best Oregon road trips.  If you are on an Oregon road trip, I highly recommend taking a long weekend drive from Medford to Eugene. Opt to not go on the main highways but instead with a detour through the Umpqua National Forest.

Starting at dawn in Medford, follow 62E into the forest and head toward Crater Lake National Park.  The scenery along the way is breathtaking, featuring tall pine trees, huge mountains, and depending on the season, a blanket of white or green. 

Umpqua National Forest offers many hikes for you to stop and stretch your legs. I recommend one of the shorter trails featuring rushing waterfalls, like Moon Falls Trail or Toketee Falls, which flows over a picturesque cliff.  My favorite thing to see on the drive are the tall pines of the Pacific Northwest, which offer a stark difference compared to all of the time I spend in the desert.

Continuing on your way, head to Crater Lake, the remains of an erupted and collapsed volcano, now filled with rainwater and melted snow. Scientists consider Crater Lake to be some of the cleanest water on the planet, and the bright blue is stunning.  Crater Lake National Park costs $30 to enter and there is lodging and camping inside the park. 

Driving out from Umpqua National Forest is just as scenic as the drive in. The entire drive from Medford to Eugene if taking this detour is just under four hours and 208 miles long, with scenic photo stops and more lush green hiking.  I recommend a long weekend for this trip, spending two nights in the forest, which allows for the most time out in nature.

Southeast Oregon

By Erika Bisbocci of Erika’s Travels

Southeast Oregon is one of the best Oregon road trips for travelers looking to get off the beaten path. It is one of the last unexplored wilderness areas of the Pacific Northwest and a place that redefines the word ‘remote.’ 

At first glance, the area appears to be an empty and barren wasteland that is far from Oregon’s main attractions. It lies in a largely forgotten part of the state that features mile upon mile of brush-covered landscapes and wide-open vistas. 

Upon closer examination, however, the area offers a treasure trove of unmissable highlights. Its seemingly barren expanses contain mountains, deserts, hot springs, and wildlife-rich marshlands. 

The perfect southeast Oregon road trip begins in either Boise or Bend. Over the course of three days, it showcases the Steens Mountain Wilderness, the Alvord Desert playa, and a collection of hot springs and geothermal areas.

The Alvord Desert is one of the unsung highlights of eastern Oregon. The desert’s main feature is a dried out lake bed—called a playa—that covers an area of 84 square miles. It is an unforgettable place to camp under a blanket of stars. 

From the Alvord Desert, the loop follows an unpaved road that highlights the dramatic features of Steens Mountain. It reveals alpine lakes, glacier-cut valleys, and stunning aerial views of the Alvord. After encompassing the highlights of Steens Mountain, the route continues along the Malheur Wildlife Refuge, toward Crystal Crane Hot Springs. 

From both Bend and Boise, the road trip loop is approximately 600 miles long. Alternatively, you can visit the highlights of southeast Oregon on a road trip between the two cities.

The Oregon Coast

By Zack Litchfield from Florida Man on the Run

One of the best Oregon road trips is hands down the Oregon Coast Highway. This beautiful stretch of road runs the entire length of the state. You’re able to travel it in any direction, though most often you will be heading north coming out of California. From the Welcome to Oregon sign north to Astoria, you will clock over 350 miles of scenic highway. The trip should take you around three days in total.

Day 1

Day one is a drive from the state line to Coos Bay. If you love hiking, then make sure to stop for the Cape Sebastian trail. It is a lovely hike through coastal rainforest with sweeping views of the ocean. Another good stop on day one, especially for families, is Prehistoric Gardens. This 50s-era roadside attraction features concrete dinosaurs spread out under a lush temperate rainforest which is sure to delight your kids.

Day 2

After staying the night at Coos Bay, your first stop in the morning is not far. The Oregon Dunes National Recreation Area is an awesome place. You can experience the dunes on foot or speed through them on an ATV! As you continue driving north, be on the lookout to stop and see Thor’s Well, an unusual rock formation right on the coast. Your final night is spent in Newport.

Day 3

Just like the day before your first stop comes quickly when you reach Yaquina Head Lighthouse. Situated on a spit of land just north of Newport, Oregon, the lighthouse is 93 feet tall and was first lit in 1873. Be sure to head down to Cobble Beach when you’re here. When the waves crash onto the rocks, the water makes it sound like a rain stick! Another great stop on your last day is Lewis and Clark National Historical Park just outside your destination of Astoria. There is a ton to see along the Oregon Coast Highway, which makes it one of the best Oregon road trips.

The Best Oregon Road Trips from Out of State

The Dalles to Seattle

By Jan of The Leisurely Drives

The Dalles to Seattle is one of the best Oregon road trips you can take. After touring around Oregon and taking in the natural beauty of its wonderful countryside, stay overnight at ‘The Dalles’. Ahead lay a one-day run (270 miles) to Seattle. It turned out to be a lovely day trip because of the natural and man-made wonders that we came across, plus the grand weather.

 After crossing Columbia Gorge en route to Goldendale, you will white dancing flashes on the horizon. These are windmill blades spinning lazily against the blue sky. Soon you can make out hundreds of gigantic wind turbines dotting the landscape.

This is one of the largest wind energy projects in the United States. Stop to take in this unusual sight and take a few photos. Further North lays Yakima Valley whose volcanic soil and warm climate make it ideal for agriculture. Stop for a breather at the Yakima Area Arboretum to look around its 46 acres of picture-postcard gardens and collection of various trees and sip the specialty refreshers.

The I-90 took us north-west to Snoqualmie Falls in Washington State. Stop to view the majestic waterfall on the Snoqualmie River. From the rim of its gorge, you can get some lovely views of the falling water, which formed a misty curtain as it poured down the cliff. There is also a park, an observation deck, and a gift shop.

You can take an easy trail or opt for another difficult trail that led down to the base of the falls. If you have more time, the Snoqualmie Pass also offers other hikes: Franklin falls, Snow Lake, Annette, and Melakwa Lake. From there it is only a short run to Seattle.

Redwoods National Park to Crater Lake National Park

By Jenny from Campsite Vibes

The road trip started from the Redwoods National Park in California but it is still one of the best Oregon road trips. I recommend taking 4-7 days for this trip so you get to experience each national park.

There are so many stops in the Redwood National Park. If you are looking for tall redwood trees, hike the Tall Trees Trail. It is a 4.5-mile round trip and takes you through some of the tallest trees. You will need a permit to hike this trail, but they are not difficult to get.

As you continue to drive up the coast, there are so many state parks in the Redwoods where you can explore the giant trees. They are full of hiking trails and beautiful drives. From there, it is around five and a half hours to Crater Lake National Park.

Crater Lake National Park is amazing, and the photos do not do this national park justice. Crater Lake is the deepest lake in the United States, and it also has no streams or rivers flowing to it. It is fed entirely by snowmelt which is why the lake is known for its clear blue color.

In Crater Lake National Park, you can drive around the rim of the lake. There are several pull out points throughout where you can look at points of interest and take photos. If you are interested in hiking, there are several hiking trails inside the park, including part of the iconic Pacific Crest Trail (PCT). The PCT crosses 33 miles of the park, 6 of which go along the edge of the rim of the lake.

Bend to Boise

By Kay Howard of The Awkward Traveller

Aside from being one of the best cities in Oregon, Bend is also the starting point for one of the best Oregon road trips! The Bend to Boise road trip is about 330 miles. The drive can be completed in a day or two. The trip itself can be a great long weekend loop.

However, if you want more time in the cities, budgeting for a week will allow you to explore both Bend and Boise. For lodging in Bend, stay at the LOGE Hotel and Hostel, which has free bike rentals for guests to explore the city. Plus, LOGE gives back to the local community in the form of access programs for youth in lower-income areas and sustainability projects for the environment.

After spending at least a day or two exploring Bend and the surrounding areas, you will start driving into the mountainous deserts of Eastern Oregon. Head to the state border to find The Pillars of Rome, one of Oregon’s most secluded destinations. The columns are a photographer’s dream, but should only add about an hour or two to your itinerary at most.

Although you’ll be really close to Boise now, make one more pitstop at Snively Hot Spring. The hot spring is free and only a quick 1-minute walk from the parking area. Then you’ll be about an hour away from your final destination, Boise. Aside from there being a plethora of amazing things to do in Boise, the road trip itself is one of the quietest in Oregon.

If you love open roads with low crowds, take the drive from Bend to Boise – you won’t regret it and it makes for one of the best Oregon road trips.

You can easily spend a couple of weeks taking one of the best Oregon road trips. From Portland to Bend, the state of Oregon is gorgeous. You can easily add on a California road trip and see the amazing things California has to offer. 

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