The Perfect Oregon Road Trip Itinerary: Must See Stops and Things to Do

Oregon is a picture-perfect coastal state in the Pacific Northwest known for its astounding views, outdoor lifestyle, and wild natural beauty. It is home to one of the largest river gorges and to the deepest lake in the United States. Discover the best it has to offer with this ultimate two week Oregon road trip itinerary.

Oregon Road Trip Summary

How many days does it take to road trip Oregon? You can spend months exploring the country’s ninth-largest state, but if you don’t have that kind of time, you can cut it down anywhere from a 5 day Oregon road trip to two weeks. 

Ideally, you should plan at least a week to two weeks to truly appreciate its beauty.

Plan your road trip along this loop starting and ending in Portland, it will take you to many of the highlights.

  • Astoria, 1 night
  • Cannon Beach, 1 night
  • Newport,1 night
  • Florence, 1 night 
  • Brookings, 1 night 
  • Crater Lake National Park, 3 nights
  • Bend, 2 nights
  • The Dalles, 2 nights
  • Portland, 2 nights

Oregon Road Trip Map

Hit Ctrl when clicking the map to open an interactive Google Map in another window.

Best Time of Year 

The best time of year to plan an Oregon road trip depends on the activities you are interested in and your budget. 

Summer is the most popular season, from wine tasting to biking in pleasant temps. But, it comes with occupied rooms and a hefty price tag. No road-tripping on the fly during peak season.

Fall is met with sunny skies, crisp air, and an array of orange, yellow, and red leaves. Even though you can expect a few sprinkles, it’s a popular time for hiking, pumpkin patches, and festivals. 

The rainy and winter season between October and May triggers lower hotel costs and fewer tourists with moderate temperatures. Winter activities include skiing, tubing, sledding, hot springs, and snowmobiling. Just make sure to pack layers!

Then spring arrives with new growth and invigorating temps; it’s a good time to see wildlife and the many waterfalls throughout the state. 

When it comes to outdoor adventure, Oregon has something to offer in any month.

HOT TIP: If you want to spot migrating gray whales on the coast, plan your visit from March through May or mid-December through mid-January.

Car Rental Tip – How to Avoid High Prices

Car rentals in Oregon – on the entire West Coast actually – are significantly higher than those in other areas of the country. When we first started researching prices, the search engines came up with $80 – $85 per day!

A tip we learned is to book offsite away from the airport and take public transportation or a Lyft to the rental company. 

Ultimately, we ended up with a Budget Rent a Car fifteen minutes from the airport and paid $29 per day with taxes and fees during peak season.


The Astoria Riverwalk is just one of the must-see things on your two week Oregon road trip!
Astoria Riverwalk in Oregon

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Day 1: Astoria

Once you pick up your rental car, kick off this ultimate Oregon road trip in Astoria, the oldest settlement west of the Rockies. Sitting on the banks of the Columbia River and only a few miles away from the Pacific Ocean, the small city is more like a historic fishing village with a Victorian flair.

If you’ve ever seen the 80’s coming-of-age film, The Goonies, then Astoria might look a little familiar to you. Hop on a pilgrimage around town and try to find all the locations. 

What to See & Do: Goonies Film Locations, Astoria Pier and Marina, Astoria Column, Cathedral Tree Trail, and Astoria-Megler Bridge.

Where to Eat & Drink: Coffee Girl, Buoy Beer Company, Bowpicker Fish & Chips, or Fort George Brewery.

Where to Stay: Waterfront Hotel with Indoor Pool & Free Breakfast, walking distance to all attractions

These starfish are just some of the marine wildlife we spotted on Oregon's coast.
Starfish on Cannon Beach, Oregon

Day 2: Cannon Beach

It’s time to hop on Highway 101, the 347-mile scenic road to discover Oregon’s beautiful and wild coastline. Cannon Beach is a short drive from Astoria so you can technically pick one or the other destination if you need to shorten your trip, but I think it deserves an overnight.

Once listed as “one of the world’s 100 most beautiful places” by National Geographic, Cannon Beach has a lot to see and do including exploring the quaint town itself.

On the Way: Fort Stevens State Park, Wreck of the Peter Iredale, Lewis and Clark National Historic Park, walk the Seaside promenade, and eat at Bell Buoy of Seaside.

What to See & Do: Ecola State Park, Cannon Beach, Clatsop Loop Trail to see Tillamook Rock Lighthouse (bring binoculars), and Haystack Rock. 

Where to Eat & Drink: Public Coast Brewing Company, Lazy Susan Cafe, Castaways, or Pelican Brewing Company.

Where to Stay: Beachfront Lodge with Continental Breakfast or Inn with Breakfast & Garden

HOT TIP: You can see all kinds of diverse marine life on Oregon’s beaches, it’s one of the top things to do when exploring the coast. The best time to go tidepooling is one to two hours before the low tide. Check the tide times here.


If you've ever seen the movie, The Goonies, then you will recognize Haystack Rock immediately.
Haystack Rock in Oregon

Day 3: Newport

There are a lot of stops along the two-and-a-half-hour drive to Newport, one of the biggest cities on the coast. From the aquarium to the glassblowing studio, there’s a lot to choose from once you get there. 

If you want to do something unique, reserve a pedal-powered quadricycle at Oregon Coast Railriders in Wheeler and go for an 11-mile jaunt through the countryside on an unused railroad track.

On the Way: Haystack Rock, Oswald West State Park, Neahkahnie Mountain Trail Viewpoint, Silver Point Interpretive Overlook, Tillamook Creamery, Cape Meares Lighthouse, Octopus Tree, Cape Lookout, Beverly Beach State Park, Cape Foulweather, Devils Punchbowl State Natural Area, and Yaquina Head Lighthouse.

What to See & Do: The Oregon Coast Aquarium, Historic Bayfront, Oregon Coast Glassworks, Hatfield Marine Science Center (it’s free with a suggested donation so you can stop in for as long as you’d like), sunset on Nye Beach, and the Farmer’s Market on Saturdays.

Where to Eat & Drink: Georgie’s Beachside Grill, Carl’s Coffee, Local Ocean Seafoods, Chowder Bowl, Rogue Ales and Spirits, or Panini Bakery.

Where to Stay: Adorable and Highly-Rated Motel with balconies and fireplaces

One of the must-see things in Newport, Oregon is Yaquina Head Lighthouse.
Yaquina Head Lighthouse in Oregon

Day 4: Florence

Discover one of the most photographed lighthouses in the United States, go underground in a large sea cave to find grunting sea lions, and explore a quiet gem on the coast. 

Around mile marker 164 you’ll find Yachats, pronounced Yah-hots, a welcoming small village at the mouth of the Yachats River. If you have time stop in Yachats Brewing for quality beer and farm-to-table cuisine. 

You’ll spend the night situated on the banks of the Siuslaw River in the charming riverfront district of Florence. 

On the Way: South Beach State Park, Seal Rock State Recreation Site, hike the one-mile loop at Yachats Ocean Road State Park, Devil’s Churn Scenic Overlook, Cape Perpetua Lookout,  Thor’s Well, and Neptune State Scenic Viewpoint.

What to See & Do: Eat on the river, Take a Dune Buggy Tour, Florence Old Town, Hobbit Trail with the China Creek Trail, Heceta Head Lighthouse, and Sea Lion Caves. 

Where to Eat & Drink: River Roasters, Homegrown, BJ’s Ice Cream Parlor, or Waterfront Depot Restaurant.

Where to Stay: Charming Motel with a Cabin-Vibe walking distance to Old Town


The top places to visit on this Oregon travel list include Crater Lake National Park, Smith Rock State Park, the Columbia River Gorge, and so much more! Here's a perfect two week itinerary that starts and ends in Portland. #pacificnorthwest #oregon
Sea Lion Caves


Day 5: Brookings

After leaving Florence, you’ll travel from sandy dunes to the untamed wild section of the drive. With mountains and forest on one side and the tumultuous ocean on the other, the scenery is spectacularly dramatic. 

More than likely, the road will be uncrowded with a quiet fishing port or artsy town popping up here and there. Four of the eleven lighthouses on Oregon’s waterfront line the southern stretch and it feels like every few miles you’re running into a state park. 

Stop just six miles short of the California state line for your overnight in Brookings, the southernmost city on the coast. 

On the Way: Simpson Reef Overlook, Face Rock State Viewpoint, Sunset Bay State Park, Shore Acres State Park, Cape Arago Lighthouse, Coquille River Lighthouse, Face Rock State Scenic Viewpoint, Sisters Rock State Park, Pelican Bay Lighthouse, and Cape Blanco Lighthouse.

What to See & Do: Samuel H. Boardman State Park, Azalea Park if visiting in the spring, Port of Brookings-Harbor Marina Boardwalk, Harris Beach State Park, and Chetco Point Park

Where to Eat & Drink: The Crazy Norwegians Fish and Chips, Tasty Kate’s, Khun Thai.

Where to Stay: Comfy Beachfront Hotel with Water Views

*If you wake up early enough the next morning, drive the extra 23 miles south to Redwood National and State Park for a detour if you’re like us and love to see all the national parks.”

Garden at Shore Acres State Park on Oregon's coast.
Garden at Shore Acres State Park

Days 6 – 8: Crater Lake National Park

Crater Lake is one of the most magical landscapes in the United States. Many people asked if our pictures were filtered and if the lake really is that blue. And I’m here to tell you yes, it really is that blue. 

Formed in the remains of an ancient volcano, at 1,943 feet deep, it is the deepest lake in the United States and one of the top ten on earth. Excellent visibility, measured at 144 feet, along with the depth and purity contributes to the brilliant blue color.

Any southern Oregon road trip should include this stop! Plan for at least three days so you can hike, take the scenic drive, and a boat tour of the lake. 

What to See & Do: Rim Village Visitor Center, Crater Lake Rim Scenic Drive, Watchman Trail, Standard Boat Lake Cruise which includes the Cleetwood Cove Trail, Garfield Peak Trail, Crater Lake Lodge, and the Discovery Point Trail. Read about our favorite hikes here at The Best Crater Lake Hiking Trails.

Where to Eat & Drink: Pack in your own lunches, Prospect Cafe, Crater Lake Lodge, and Prospect Pizza.

Where to Stay: Hotel & Suites near the Park or Mountain Cabin with Balcony


Any southern Oregon road trip would not be complete without a few days at Crater Lake National Park. Crater Lake is jaw-dropping beautiful.
Told you it really is THAT blue

Days 9 – 10: Bend

If looking up real estate the first day of a visit is any indication of how impressive an area is then Bend is uber awesome. You’ll only be able to scratch the surface of all this mountain town has to offer within a few days so you’ll definitely be planning another trip back.

Situated in the foothills of Oregon’s Cascade Range, the upscale community is at the core of an outdoor playground with countless activities throughout the entire year. The attractive downtown area has a wide range of hip coffee shops, local eateries, and innovative art galleries.

On the Way: Take the Cascade Lakes National Scenic Byway and pull over at a few of the lakes with lunch or drinks at Elk Lake Restaurant. 

What to See & Do: Try a local craft brewery, Todd Lake Loop Trail, Walk around Downtown, Tumalo Falls, Old Mill District, and Smith Rock State Park.

Where to Eat & Drink: The Cafe, Crux Fermentation Project, Spork, Bangers & Brews, and Wild Rose Northern Thai Eats.

Where to Stay: Welcoming Hotel with Free Breakfast, Beautiful Views in a Great Location near the Old Mill District.


Days 11 – 12: Columbia River Gorge 

Let’s adventure into America’s largest National Scenic Area, the Columbia River Gorge. Separating Washington and Oregon, this vast meandering canyon delivers breathtaking views, gorgeous waterfalls, and endless outdoor activities.

From the historic Crown Point Vista House to the horseshoe-shaped Rowena Crest viewpoint, it is a drive that you will never forget.

On the Way: Detour to Mount Hood, Oregon’s highest mountain, and hop on the Scenic Sky Chairs for a bird’s-eye view of the surrounding mountain ranges. 

What to See & Do: Elowah Falls, Bridge of the Gods, Multnomah Falls, Latourell Falls, Crown Point, Bonneville Lock and Dam, Bridal Veil Falls, Rowena Crest, Horsetail Falls, Wahkeena Falls, Hood River, and the Vista House.

Where to Eat & Drink: Thunder Island Brewing Co, The Gorge White House, Full Sail Brewing Company, Tad’s Chicken N’ Dumplins, and Columbia Gorge Hotel.

Where to Stay: Hidden Gem of a hotel with Fantastic River Views

HOT TIP: Include the 35-mile Hood River County Fruit Loop to your itinerary for a scenic drive with charming orchards, bountiful vineyards, fruit stands, and even an alpaca ranch. 

On any visit to Oregon, make sure to include Columbia River Gorge on your itinerary. Designated the largest National Scenic Area in America, the canyon is a must-see.
The breathtaking Columbia River Gorge

Days 13 – 14 Portland

The City of Roses pounds to an eclectic beat, and with its prime location in the Pacific Northwest there are a ton of things to do outdoors including gardens and parks. Read here for other Outdoorsy Day Trips from Portland. 

Bearded hipsters, emerging artists, and skilled brewmasters converge amid two mountain ranges to form Portland. With that in mind, there’s no shortage of breweries, galleries, coffee shops, donuts, or food trucks within the metropolis.

What to See & Do: Portland Japanese Garden, Washington Park, Best Rooftop Bars in Portland, International Rose Test Garden, Pioneer Courthouse Square, Powell’s City of Books, and Pittock Mansion. 

Where to Eat & Drink: Rogue Ales, Hawthorne Asylum Food Cart Pod, Radio Room, Culmination Brewing, Homegrown, Voodoo Doughnut Old Town, and Prost!

Where to Stay: Boutique Hotel with Bike Rental and Wine Reception

HOT TIP: If you don’t want to spend the money for the Japanese Garden, you can link from the MAC trail to a series of switchbacks on the Wildwood Trail for a glimpse overhead. 

How to plan the ultimate Oregon trip! Check out this 14-day itinerary of all the best things to see and do including the Portland International Rose Garden.
Portland International Rose Test Garden


Have you taken an Oregon road trip? What do you recommend?

Pin it for Later!

On this awesome Oregon road trip, you'll drive the entire coast, explore Crater Lake National Coast, discover the Columbia River Gorge, and hike in one of the most beautiful state parks. #oregon #roadtrip

The top places to visit on this Oregon travel list include Crater Lake National Park, Smith Rock State Park, the Columbia River Gorge, and so much more! Here's a perfect two week itinerary that starts and ends in Portland. #pacificnorthwest #oregon

Check out the must-see places to visit along an Oregon coast road trip and beyond. From hiking in Bend and Crater Lake National Park to exploring the city of Portland and Columbia Gorge, this will be an American vacation you'll never forget. #oregon #bucketlists


Follow Angela:

Angela E. is a travel writer from the Chicagoland area who has visited all 50 states in the US and has traveled extensively around the world. She is passionate about exploring the great outdoors and hiking in particular. Her love for nature has taken her to some of the most beautiful locations on the planet. She has written extensively about her travels on her own website, Dang Travelers, and has been published in collaboration with other travel websites and multiple visitor bureaus around the country.

5 Responses

  1. Dan Coleman

    I enjoyed reading about your trip all over Oregon. By any chance do you remember the exact Budget Rental car location address you picked up your car?

  2. Dwana

    Were the hikes you mentioned fairly easy?
    What about ticks, Is that something to prepare for?
    And last, do you think this could be done in a week? I know we wouldn’t be able to spend several nights in each place and wouldn’t be able to do or see everything but the highlights.

    • Dang Travelers

      A week is pretty short for the entire loop, but you might be able to swing it. There are some great hikes in Crater Lake, but you could also just spend a day there (take the boat ride and see the views from the overlooks) and drive the coast.

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