Last updated on September 25th, 2023 at 01:38 pm

Oregon (pronounced “Ore-gun”, not “Ore-gone”!) is often overshadowed by its extremely popular neighboring state of California in the US. But if you are looking for a road less traveled then you have to take an Oregon road trip. In this blog post, we will share our detailed itinerary including what to see, do, and where to stay.

Below is a map of the route we took on this trip, click here to go to Google Maps. We drove across the state in a clockwise direction but you can do the same in an anti-clockwise direction as well. If you remember we did a similar 7-day road trip in Iceland and trust me when I say that our Oregon road trip was just as adventurous. Don’t forget to check out our post on waterfalls near Portland for more incredible inspiration.

FUN FACT: Oregon is the only other state in the US after New Jersey to have assistants at gas stations to fill gas in your car.

How Many Days Do You Need for an Oregon Road Trip?

We were able to make this a total of the 10-day trip including travel time. If you follow our Oregon itinerary you will have plenty of time to go on hikes, take wine tours, and relax on this road trip.

You can easily make this a 7-day road trip and we’ll tell you how in the modified itinerary below. However, if you have less than 7-days then I suggest visiting only Portland, Columbia River Gorge, Mt. Hood region, & Cannon Beach from the itinerary below.

Disclaimer: This post contains affiliate links.

Related Read: SF to LA – An ultimate west coast road trip guide

Starting point 

We flew into Portland and spend 2 days in the city before starting our road trip. TIP: You do not need a car in Portland city so save yourselves some cash by renting a car the day you hit the road.

Portland would be our recommendation as a starting point for all those who are flying into Oregon. For those who are driving from the South i.e. California, the best starting point for you would be either the coast or Crater lake in this loop.

Oregon Road Trip Itinerary

Below is our detailed itinerary is broken out by each day. If you want to do a 7-day road trip then we have listed where it makes the most sense to skip things.

Day 1 & 2 – Portland

After you land in Portland spend 2 days in this funky city. We not only explored the city landmarks but in reality spend the entire weekend food binging in Portland. TIP: If you want to make this a 7-day road trip then spend just 1 day in Portland.

We will be writing a separate post on what to do on a weekend in Portland. But to highlight a few things –

• Eat your heart out in the food capital on the west coast. From food trucks to delicious worldwide cuisines all around town you’re going to return with some additional baggage on your body.
• Check out the largest bookstore in the world – Powell’s Bookstore
• Must eat doughnuts (try both Bluestar & Vodoo doughnuts to give your own verdict no matter what the locals say)
• Take a walking city tour or a Segway tour to learn more about the city
• Check out the Japanese Garden

ACCOMMODATION: It usually nice if you stay in either downtown or the pearl district so you’re walking distance away from all the things –

• Hilton Portland Downtown or the Hampton Inn Pearl District
• The Bidwell Marriott Portland or the Courtyard Marriott City Center

Day 3 – Columbia River Gorge Waterfalls & wineries

Fasten your seatbelts and drive to the Columbia River Gorge which is only 30 minutes away from Portland. If you start driving early in the morning, you’ll easily be able to cover all the stopovers mentioned below in that order. For more details, read our in-depth blog post on Columbia Gorge road trip.

• Portland Women’s Forum vista point (has the best sunrise view if there are no wildfire smoke)
• Latourell Falls (add a short 2.4 mile hike here)
• Multnomah Falls
• Bridal Veil Falls (add a short 1.2 mile hike here)
• Starvation Creek Falls
• Wineries tour in Mt. Hood/Gorge

ACCOMMODATION: Spend the night in White Salmon, WA or Hood River, OR

Find fun things to do in Oregon during your road trip!

Day 4 – Explore Mt. Hood Region

We spent 2 nights in Mt. Hood region which gave us the time to not only explore but also relax in the most gorgeous setting. There are a ton of outdoor activities to do here so spending only 1 day would be an injustice to this region. We have broken down the activities by each day for you –

• Explore Hood River town which is known as the world’s kite surfing capital, perhaps indulge in some water activity or grab lunch here
• The Gorge White House makes for a great stop for Apple cider tasting and fresh fruit & flower farm
• If you happen to visit in spring don’t forget to check out the “fruit loop” trails for spring blossoming trees.
• Drive to the historic Timberline Lodge and either take the chair lift to get to the summit or if you are up for an adventure there are tons of hiking trails behind the lodge. We did a section of the zigzag overlook trail which starts at the lodge parking area. Ask the lodge visitor center for more info on trails. Enjoy a nice early dinner or a cup of coffee with a view.
• If you are not up for visiting the lodge then consider hiking the Mirror Lake loop trail that afternoon. We skipped the mirror lake loop.
• Return to Government Camp for dinner unless you are staying back at Timberline Lodge.

ACCOMMODATION: Spend the night in Mt. Hood region. We stayed in a gorgeous farmhouse surrounded by apple & pear orchards booked through Airbnb. Your other best option is to stay at the historic Timberline Lodge or hotels in Government Camp, a small town in Mt. Hood region.

Day 5 – Explore Mt. Hood Region

Here’s what to do on your second day in Mt. Hood region –

• Hit the Tamanawas Falls hiking trail in the morning (alternatively, you can do the Mirror Lake loop). Tamanawas trail is amazing, take our word for it.
• Have your lunch at Tamanawas Falls. Pack your lunch with you so you can eat with the waterfall views at the end of the hike.
• After lunch head to Trillium Lake in the afternoon. Walk along the lake trail or rent a kayak and enjoy the serene Mt Hood view from the water. TIP: Book your kayak rental in Govt Camp as there are no rental facilities at Trillium lake. The rental company will bring your kayak to the lake area. Don’t miss the sunset at Lake Trillium! TIP: Bring mosquito spray, there are like a thousand of them here. You can also rent campgrounds at Trillium lake if you want to camp in this area.

ACCOMMODATION: We stayed back at the same farmhouse Airbnb with the perfect view of Mt. Hood. Your other best option is to stay at the historic Timberline Lodge or hotels in Government Camp, a small town in Mt. Hood region.

Day 6 – Smith Rock State Park, Painted Hills & 3 Sisters

As you drive south from Mt. Hood, take a day to explore the desert region of Oregon. You’d be surprised to know that a big part of Oregon is, in fact, desert land. What was really fascinating to us was that our families in India instantly knew about Oregon out of all the places. They were the ones to tell us about Rajneeshpuram. FACT: Rajneeshpuram (from ‘Wild Wild Country’ series on Netflix) was not too far from this part of Oregon.

TIP: For a 7-day Oregon road trip, skip this section and head straight to Crater Lake from Mt. Hood.

• Stop at Smith Rock State Park as you drive south from Mt. Hood region. and enjoy the gorgeous scenery.
• Drive about 2 hours east to see the Painted Hills which are in the deep end of the Oregonian desert.
• Reach Bend and head to Summit Park for a great view of the 3 Sisters volcano peaks.
• If you want to get a better view of 3 sisters then drive 30 mins from Bend to Dutchman Flat Sno Park in Deschutes National Forest.

ACCOMMODATION: Spend the night in Bend, OR.

Day 7 – Crater Lake National Park

Crater Lake National Park is about 2 hours away from Bend or about 4 hours from Govt Camp. If you leave early in the morning, you can reach Crater Lake just in time to drive around the rim and see the following viewpoints & sneak in one easy hike.

Pick and choose your favorite spots to see in Crater Lake National Park, below are a few that we recommend –

1. Sinnott Memorial Outlook at Rim Visitor Center
2. Sun Notch (0.8 miles easy hike with views of Phantom Ship)
3. Phantom ship overlook
4. Discovery Point (2 miles)
5. Watchman Peak (1.6 miles moderate steep hike)
6. Pumice castle overlook,
7. Cloudcap overlook,
8. Vidae Falls
9. Pinnacles Overlook.

ACCOMMODATION: Spend the night in Crater Lake Lodge or campgrounds in the park. If you don’t get a reservation in either of these then consider staying in Fort Klamath or Chemult or Chiloquin which are small towns near Crater Lake. TIP: If you stay at Crater Lake Lodge, then don’t miss the splendid sunset from the lobby’s back patio.

PLEASE NOTE:  The Crater Lake itinerary was a part of our original plan until west coast wildfires & smoke completely ruined the experience. When we arrived at Crater Lake National Park, it became really difficult to breathe without inhaling the fumes. Not to mention, the visibility of the Lake was near zero. We had booked a campground for the night but for good reasons we decided to turn around. As a backup plan, we headed to spend more time on the Oregon coast. PRO TIP: Watch out for wildfire and smoke reports in Oregon before you head here!

Day 8 – Umpqua National Forest & drive to Eugene

Next morning stop by the Crater Lake vista points that you might’ve missed on the previous day. On your way to the coast of Oregon, you must take a pitstop at Umpqua National Forest for a bonus waterfall & hidden hot springs.

• Drive around Crater Lake in the morning to cover any missed vista points from the previous day.
• Hike the Toketee Waterfall trail in Umpqua National Forest as you exit Crater Lake. It’s an easy 0.8 miles round trip hike to the gorgeous waterfalls as you can see in our photos.
• If you enjoy natural hot springs, then as you exit from Toketee waterfalls take a left and head to Umpqua Hot Springs. There is a $5/vehicle charge to park at the hot springs. Clothing is not enforced here so consider yourself forewarned. In full disclosure, we did not visit the hot springs due to a lack of time.
• Drive to Eugene from Toketee Falls should take around 2.30 hrs.

ACCOMMODATION: Spend the night in Eugene, OR.

Day 9:  Oregon Coast road trip

The next morning we headed to Florence from Eugene where we started our Oregon coast drive. The coastal drive takes you on Highway 101 which, in fact, is a continuation of California’s coast to Oregon’s.

Given that we just had one day set aside for this Oregon coast road trip, we only stopped at the vista points mentioned below in bold. We’ve listed some additional awesome pit stops along the way if you have more time.

• Drive past Florence 
• Heceta Head Lighthouse  Scenic Viewpoint (There is a B&B at this lighthouse now) or stop at Sea Lion vista point to see the lighthouse from a distance.
• Cape Perpetua Overlook (Thor’s Well is another stop before turning right to Cape Perpetua overlook)
• Yachats (stop by for a drink or early lunch)
• Newport (If you skip Yachats then stop here for lunch)
• Devil’s punchbowl and Otter Rock
• Tillamook (stop by at the cheese factory or the Tillamook ice-creamery)
• Cannon Beach, get here before sunset to watch the magic unfold

ACCOMMODATION: Spend the night in Cannon Beach, OR.

Day 10: Lewis & Clark National Park OR Evergreen Aviation Museum

We took a red-eye back to the east coast since we wanted to squeeze every second of our last day. TIP: For a 7-day Oregon road trip, skip this part and fly out on your last day.

• We visited the Evergreen Aviation & Space Museum in the morning but you can choose to visit the Lewis & Clark National Park near Cannon Beach to get an insight into expeditions that were an integral part of US history.
• Head back to Portland to grab an early dinner before heading out to the airport for an evening flight.

Phew, another long guide, isn’t it? But there is so much to see & do here that you have to plan it right and we’ve to give all the right info to do so. And by the way, if Oregon wasn’t on your list, we sure hope it is now!

If you liked this extensive Oregon road trip planning guide then don’t forget to share it along with family & friends.

More on Travel in the United States:

• America’s favorite road trip – the Blue Ridge Parkway
• Bucket List Arizona Road Trip – The perfect long weekend 4-day itinerary
• Best places to see fall colors in New Hampshire – A Roadtrip through New England
• Ultimate SF to LA Road trip – Best stops along California’s Pacific Coast Highway

Happy Traveling!