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21+ Spots That Will Inspire Your Next Road Trip to Oregon

Oregon Travel Insider Guides
by Katie Scott Aiton Apr 10, 2017

Editor’s note: These spots are all taken directly from travelstoke®, a new app from Matador that connects you with fellow travelers and locals, and helps you build trip itineraries with spots that integrate seamlessly into Google Maps and Uber. Download the app to add any of the spots below directly to your future trips.

1. Historic Columbia River Highway Scenic Byway via US 30, I-84.

A road trip in Oregon is just not complete unless you’ve experienced the surreal 70-mile drive through the Columbia River Gorge, a National Historic Landmark that also happens to be America’s first scenic highway.

Columbia River Gorge National Scenic Area

 Columbia River Gorge National Scenic AreaHood River, United States#hiking

Drive along the scenic Columbia River, lush green forest, and waterfalls. Be sure to stop at one of the numerous hiking trails along the way to truly realize the beauty that is the Columbia River Gorge.

Make a stop at Vista House for a breathtaking view of the Gorge from the rotunda at Crown Point. If you want to see the famed yet often crowded Multnomah Falls and have time to kill, hike the five-mile Multnomah-Wahkeena loop and pass through forest lands of fairy tale essence  – as well as eight waterfalls. Start at the Wahkeena trailhead as Multnomah is heavily trafficked. While driving through Cascade Locks visit Eastwind Drive-In for a monster-sized ice cream cone.  Hood River is also a must-stop if you like quality craft beer, home of Double Mountain Brewery (get the pizza here), Full Sail Brewery, and Friem Family Brewers, to name a few.

Dog Mountain Lookout

 Dog Mountain LookoutStevenson, United StatesOne of the most difficult Columbia Gorge trail heads. Beautiful in the spring because of the wildflowers. Pack smart, wear hiking boots and expect one heck of a climb #outdoors #familyfriendly #columbiagorge #extreme #hiking

2. Hells Canyon Scenic Byway via OR 82, Imnaha Road, FR 39, OR 86, I-84, OR 203.

This 208-mile horseshoe route has it all – rugged canyons, forested mountains, desert, and river. Depending where you are, start in La Grande or Baker City, both of which have vibrant downtowns and are good places to get some road snacks and gas – be sure to fill your tank before leaving as fuel stops are limited on this trip.

Seven Devils Campground

 Seven Devils CampgroundRiggins, United States#hiking #snow #camping
There’s a 26 mile loop around the Seven Devils that’s good for hiking and packing and hunting. Seven Devils is part of Hell’s Canyon, which runs along the western border of Idaho.

Hells Canyon is the deepest gorge in the US. From FR-39 turn onto FR-3965 near the Ollokot campground and look down onto the canyon from Hells Canyon Overlook. Better yet, experience Hells Canyon National Recreation Area to its fullest by signing up for a rafting trip along the Snake River. For some culture, make a stop in Joseph, a small western arts town that happens to be a nice gateway for Wallowa Lake, a scenic base wedged amongst the majestic glacial peaks of the Wallowa Mountains. From Wallowa Lake, you have easy access to Eagle Cap Wilderness, which has a plethora of trail options for hikers and horseback riders.

Snake River

 Snake RiverRiggins, United StatesBackpacking along the Snake River. This trail runs from Pittsburgh Landing out towards Kirkwood Ranch and much farther beyond. Watch out for snakes in the late summer. And bring your fishing pole!

#rivertrail #horsebackriding #hiking #camping

Travel this route anytime from June through October since parts of the byway are closed during winter due to snow.

3. Volcanic Legacy Scenic Byway via US 97, OR 138, OR 62.

Thousands of years ago, a massive eruption caused a volcano to collapse, thus making way for the caldera that created Crater Lake, home to Crater Lake National Park.

Crater Lake National Park

 Crater Lake National ParkKlamath County, United StatesMount Mazama blew up 7,000 years ago, and now we have this bad boy. Utterly incredible. Definitely bring your wide angle lens. #nationalpark #hiking #photography

At 1,943 feet, Crater Lake is America’s deepest lake, and apparently our most pristine.

If you are starting this trip in Medford, be sure to fuel up at BricktownE Brewing Company.

BricktownE Brewing Company

 BricktownE Brewing CompanyMedford, United StatesCheap awesome beer. Amazing burgers. All a girl needs. Lemme know how the pulled pork tater tots are…dying to know. #beer #cheap-eats

After burgers and before you hit the road RoxyAnn Winery in Medford is also worth a visit.

RoxyAnn Winery

 RoxyAnn WineryMedford, United StatesTotally cute winery. Good wine, can wander the fields, pumpkin patch. Romantic, good views of the hills. #wine

Stop at Merriam Point for some epic scenery. Then take your time driving clockwise along the 33 mile Rim Drive encircling the electric blue lake so that you can easily stop at one of the many overlooks.

Rim Village

 Rim Village Café and Gift ShopKlamath County, United StatesIf you don’t want to snowshoe or cross country ski across avalanche zones and otherwise sketchy terrain, you’ll be happy to know that this view exists from the parking lot of Rim Village. As long as the road is open, you can get up to this vista within a minute. Kids can play here and you don’t need snowshoes, but be mindful of the (marked) edges. The coffee sucks and wifi is $4 for an hour, but if you’re desperate, it’ll do the trick. #snow #nationalpark #winter

Be sure to stop at the Cleetwood Cove trailhead, the only trail that leads down to the water’s edge.

Watchman Peak Trail, Crater Lake

 Watchman Peak Trail, Crater LakeKlamath County, United StatesAnother picture of Crater Lake at sunrise

Also along the route, OR 62 takes you to Upper Klamath National Wildlife Refuge, where you can find Oregon’s largest lake, Upper Klamath Lake, an area that attracts more than a million migrating birds.

4. Pacific Coast Scenic Byway via US 101.

Since there’s a ton to see and do along Oregon’s 363-mile stretch, we suggest you plan it in segments to get the most out of the trip.

Devils Punchbowl State Natural Area

 Devils Punchbowl State Natural AreaOtter Rock, United StatesHome to a close-knit surfing community, the Devil’s Punchbowl and, yes, a bunch of otters. Good for a quiet weekend getaway #oregon #coast #beach #outdoor #surfing

Spend some time exploring the rugged landscape, where hikes are plentiful and artsy beach towns abound.

Heceta Head Lightstation

 Heceta Head LightstationFlorence, United StatesThe most epic B&B in Oregon overlooks a few coves and is surrounded by trails and woods to explore. The perfect #romantic getaway spot. #Oregon #coast #beach #lighthouse

While passing through Newport be sure to stop at the Oregon Coast Aquarium and after take in the view from Yaquina Bay Lighthouse.

Oregon Coast Aquarium

 Oregon Coast AquariumNewport, United StatesNot the biggest aquarium but makes up for it with variety. The deep sea tunnel is a big crowd pleaser and the aviary section makes this aquarium unique #aquarium #museum #interactive #liveanimals #kidslearning #activekids #familyfriendly

Climb sand dunes at Oregon Dunes National Recreation Area, and visit Cannon Beach to see the 235-foot Haystack Rock.

Sand Dunes Frontier

 Sand Dunes FrontierFlorence, United StatesOne of the more exhilarating outdoor excursions on the coast. Rent a dune buggy ride or just experience the joy of rolling down massive sand dunes #oregon #coast #beach #dunes #outdoor

For some nice coastline views, hike in Ecola State Park near Cannon Beach or the Cape Lookout Trail in Tillamook, where if you’re there during winter you have a good chance of seeing whales migrating south.

Ecola State Park

 Ecola State ParkSeaside, United StatesThe closest beach hike from Portland, hiking the head is perfect for a summer escape to the sea. Be sure to check out #indianbeach while you are there. #summer #kidfriendly #outdoor #hiking #camping

Cannon Beach

 Cannon BeachCannon Beach, United StatesHaystack Rock. Cannon Beach is a nice small tourist town Visit Ecola SP north of town.

Finally, you want to stop in Astoria, a quirky city with Victorian homes, antique shops, Fort George Brewery, a corny but fun tram ride, and the unassuming Columbian Cafe, which serves up a great brunch. Oh yeah, and The Goonies was filmed in Astoria.

5. Mount Hood Scenic Byway via US 26, OR 35.

Visible from Portland, Mount Hood is not only an iconic landmark in Oregon but a great place to adventure around pretty much any time of year. Fortunately, there is a scenic drive that curves along the base of the mountain, affording incredible views. If you have time to spare, take a leisurely drive along the Hood River County Fruit Loop, a fertile valley where you will zoom past pear and apple trees, berry farms, and fields of lavender.

Mount Hood National Forest

 Mt. Hood National ForestSandy, United StatesOregon is home to some of the most scenic forests I have ever driven through. SR 35 is part of the Mount Hood Scenic Loop where I stood staring up at the towering 11,000 plus feet face of Mount Hood.

#hiking #snow #camping #oregon #pnw #scenicdrive

Approaching Mount Hood, you will soon be passing through Mount Hood National Forest, lined with old-growth Douglas fir.

Mount Hood

 Mount HoodMount Hood, United Stateswe were tryibg to see crater lake but were detoured because of all the snowfall. a bit further down the road was the entrance to the park with this incredible view and families sledding. it was magical #nature #oregon #snow

If you’re into winter sports, Government Camp is a paradisal haven for skiing and snowboarding. If you’re not into that, head up the 6- mile (very steep) road to Timberline Lodge and get drunk on hot toddies. There are multiple day hiking options too.

East Fork Tamanawas Falls Trailhead

 East Fork Tamanawas Falls TrailheadMount Hood, United StatesEverybody’s favorite waterfall on the backside of the Hood in wine country. Short, easy hike with a pretty incredible finish #outdoor #mounthood #waterfall #hiking #activekids

The exterior of Timberline might look familiar if you’re a fan of The Shining since it was filmed there. From Timberline you have a sweet view of Mount Hood’s summit, so it’s worth the drive up. While in the area you will probably want to head to Bagby Hot Springs for some much-needed relaxation – just note that it’s clothing optional.

6. Journey Through Time Scenic Byway via US 97, OR 218, OR 19, US 26, OR 7.

As the name implies, this route showcases some history. Along US 97, make a stop at Shaniko, a living ghost town that has been restored as a tourist stop complete with kitschy shops, tours, and annual events. Continue east onto OR 218 and you will reach the John Day Fossil Beds National Monument where all along the byway you’ll find prehistoric fossil beds, some dating back 54 million years. Get out and explore the interpretive trails to learn more about the fossils. Then for more ancient stuff, head to the Painted Hills, a colorful landscape where you’ll see years of earth’s history layered in a trippy collage of red, yellow, gold, and black soil.

Painted Hills

 Painted HillsMitchell, United StatesA long way from anywhere but worth checking out this geological wonder! #hiking #photography

From here there are a number of trails if you wish to explore the region more. As you weave along US 19 you are promised more spectacular views of the Painted Hills. Continue onto US 26 and pass through Prairie City, a scenic drive with views of the Strawberry Mountain Wilderness and then up into the Blue Mountains on OR 7. Eventually, you will reach Whitney, a ghost town with a bunch of abandoned buildings, until the byway meets up with Elkhorn Drive Scenic Byway, finishing your journey in Baker City.

7. McKenzie Pass-Santiam Pass Scenic Byway via US 20/US 126, OR 126, OR 242.

Start in the town of Sisters for some food and fuel, and maybe pop into a few galleries and antique shops while you’re at it. We recommend Sisters Bakery for a freshly baked doughnut and caffeinated beverage. Following the byway on US 20/US 126, you will come to Santiam Pass, a 4,817 foot pass that cuts through the Cascade Range. Here you will find some volcanic features and ashen buttes. Eventually, you will reach the McKenzie River Highway, where you can get out and explore the hiking and mountain biking trails of McKenzie River National Recreation Area. It’s also just a nice spot to laze about by the river. Further along the byway, you will come to Clear Lake, where you can walk a five-mile trail around the lake or paddle around on a canoe. Then head east on OR 242 on McKenzie Highway where you will have yet more volcano views before coming to McKenzie Pass, an epic 65-mile stretch of lava that resulted from an eruption around 2,000 years ago. Finish off at Dee Wright Observatory for panoramic views of different mountain peaks as well as a short interpretive paved hike along the lava beds.

8. Cascade Lakes Scenic Byway via OR 372, FR 41, FR 46.

Central Oregon is definitely worth exploring, and if you plan on visiting Bend, we recommend taking a drive on the Cascade Lakes Highway, where you will find forest roads, mountains, and well, lakes. Begin with lunch (or finish with dinner, depending) at Crux Fermentation Project.

Crux Fermentation Project

 Crux Fermentation ProjectBend, United StatesMy favorite brewery in Bend. Great dog- and kid-friendly outdoor area. Limited food menu, but complements their great beers perfectly. #brewery #beer

Heading westward on OR 372 (Cascade Lakes Highway) you will enter Deschutes National Forest, a canopy of pine, fir, and hemlock. If fishing or canoeing is a thing you do, get off at FR 41 for river access and while away some time by the Deschutes River.

Deschutes River

 Deschutes River AdventuresMaupin, United StatesWhitewater rafting for the extreme crew and multi-day family vacations. Also not a bad place to get a tan in the summer #whitewaterrafting #camping #extreme #nature #outdoors #familyfriendly #activekids

Continue on towards Mt. Bachelor, where you have the option for skiing as Mt Bachelor Ski Resort happens to be the largest ski area in Oregon. Snow usually lasts through June. If you are there during summer you can ride a chairlift to the Pine Marten Lodge for some killer views that reach all the way to Washington and California.

Make your descent, check out Broken Top Mountain as you pass by, and then get ready for some lakes. Sparks Lake and Devils Lake are worth checking out if you have time. But don’t worry, there are still more to come if you just want to continue on the road. The byway eventually takes you south on FR 46, where there is opportunity to get off and hike to the many lakes hidden within the Three Sisters Wilderness. Consider stopping at Elk Lake Recreation Area for easy water access and views of Mt. Bachelor. Then continue on as the byway weaves along the Deschutes River, passing Little Lava Lake and Crane Prairie Reservoir.

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