8 Days in Oregon – The Perfect Road Trip Itinerary

If Oregon has been on your bucket list of travel destinations but you don’t know where to start, look no further because I spent hours researching before executing the perfect road trip itinerary. We packed a lot into our one-week (8-day) trip and I’ve outlined all of the travel itinerary details below.

Road Trip Day 1 – Portland

Our first day was a travel day but we were fortunate enough to have an early flight that allowed us almost a full day of exploring. Step one for our Oregon road trip was to get a rental car but step two was definitely to get some of the incredible food and drinks Portland has to offer.

What to eat and drink:

• Tusk – This is number one for a reason! A must go if you love Mediterranean food.
• Screen Door Pearl District
• Multnomah Whiskey Library – The Green Room
• Deschutes Brewery – Portland Public House

Where to stay:

• The Bidwell Marriott Portland

What to do:

• Visit Powell’s Books
• Explore the city! There are so many great shops and a bonus of no sales tax.

Road Trip Day 2 – Beaverton / Willamette Valley

I organized the Oregon road trip itinerary counterclockwise so the next stop in the loop was to head towards Willamette Valley. On our way there we stopped in Beaverton to see a friend.

What to eat and drink:

• Tom’s Pancake House (Beaverton)
• Central Station Taps (Beaverton)
• Red Hills Market (Dundee)

Where to stay:

• The Setting Inn (Willamette Valley)

What to do:

• Tour Nike Headquarters (Beaverton) – If you’re lucky enough to know an employee I highly recommend.
• See a movie (Newberg)
• Wine tasting! – More on this in Day 3.

Road Trip Day 3 – Willamette Valley

I definitely recommend allowing at least one full day to enjoy wine country. We were able to fit in two wine tastings + lunch and dinner which I felt was a good amount to fit in one day without feeling rushed. Plus, now we have an excuse to come back again to try more.

What to eat and drink:

• Field + Stream (Dundee)
• Trellis (Dundee)

Where to stay:

• The Setting Inn (Willamette Valley)

What to do:

• Penner Ash 60 min tasting
• L’Angolo 90 min tasting

Road Trip Day 4 – Oregon Coast

There’s just nothing quite like driving down the Oregon Coast! Our goal was to hit some of the major scenic viewpoints as we made our way south and the views did not disappoint.

What to eat and drink:

• Pelican Brewing Pacific City Brewpub (Pacific City)
• Ben and Jeff’s Burgers and Tacos (Pacific City)
• The Drift Inn and Restaurant (Yachats)

Where to stay:

• Bay Point Landing (Coos Bay)

What to do:

• Cape Kiwanda (Pacific City)
• Devils Punchbowl (Otter Rock)
• Yaquina Head Lighthouse (Otter Rock)
• Thor’s Well (Yachats)
• Cape Perpetua (Yachats)

Road Trip Day 5 – Oregon Coast (Coos Bay)

We had an extra day on the coast scheduled in our Oregon road trip so we explored some of the state parks clustered within the Coos Bay area. The rock formations were incredible and the Pacific Ocean is gorgeous.

What to eat and drink:

• The Grounds Cafe (Coos Bay)
• 7 Devils Waterfront Alehouse (Coos Bay)
• Shark Bites Cafe (Coos Bay)

Where to stay:

• Bay Point Landing (Coos Bay)

What to do:

• Oregon Dunes National Recreation Area, John Dellenback Trail
• Shores Acres State Park
• Cape Arago State Park
• Sunset Bay State Park

Road Trip Day 6 – Crater Lake / Bend

Get your podcasts ready because this day was the longest day of driving. Throughout my Oregon road trip research I was wavering between whether or not Crater Lake was worth the drive, but after seeing it in person I can say it is 100% worth it. Photos do not do it justice.

What to eat and drink:

• Drive through The Grounds Cafe (Coos Bay) before hitting the road
• Lunch on the road (we found a Subway) or Crater Lake Rim Village Cafe
• Dinner at Wild Rose (Bend) – This deserves its own blog post it is that good!

Where to stay:

• We were lucky to be visiting and staying with a friend but if we didn’t I would look into Marriott SpringHill Suites Bend.

What to do:

• Explore Crater Lake
  • Drive around the lake
  • Stop at Vidae Falls

Road Trip Day 7 – Bend

Bend was probably my favorite stop on the trip and we spent most the day paddle boarding on Elk Lake. It was a perfect day and I can’t wait to go back to explore all that Bend has to offer.

What to eat and drink:

• Bo’s Falafel Bar
• Boss Rambler Beer Club
• Wild Rose – Again, worth repeating it is so good.
• The Bob Bend (food cart)
• Nancy P’s Cafe and Bakery

Where to stay:

• We were lucky to be visiting and staying with a friend but if we didn’t I would look into Marriott SpringHill Suites Bend.

What to do:

• Deschutes River
• Drake Park – There was a Munch & Music going on when we visited
• Paddle board on Elk Lake

Road Trip Day 8 – Mt. Hood / Hood River

For the last full day or our Oregon road trip itinerary we made our way up to Mt. Hood, Hood River, and then traveled through Columbia River Gorge back to Portland. You could spend full days at all of those locations so definitely keep in mind that we only barely scraped the surface on this day.

What to eat and drink:

• PFriem (Hood River)
• Sugarpine Drive-in – We wanted to stop here on our way from Columbia River Gorge to Portland but it was unfortunately closed.

Where to stay:

• We ended our epic Oregon road trip itinerary back in Portland and stayed at the Moxy Portland Downtown for a quick drive to the airport in the morning.

What to do:

• Trillium Lake (Mt. Hood)
• Timberline Lodge (Mt. Hood)
• Hood River Lavender Farms (Hood River)
• Multnomah Falls (Columbia River Gorge)

That’s a wrap for our Oregon road trip itinerary! Please let me know in the comments if you have any questions. Any recommendations I missed?