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Oregon Road Trip Itinerary: 10 Destinations You Can’t Miss

Oregon Road Trip Itinerary_10 Destinations You Can't Miss

Oregon is one of our favorite places on Earth!  With so much diversity in ecosystems, it’s hard not to fall in love with Oregon. This Oregon road trip itinerary will take you to moss-filled forests, sparkling rivers and lakes, rumbling waterfalls, wonderful farmer’s markets with locally grown food, picking wild blackberries and organic fruit from orchards, affordable and immaculately clean campgrounds, and massive walls of limestone rock.  Add in the fact that almost everyone I’ve met on my travels through Oregon is super nice, it’s hard to go wrong if you choose Oregon for your next road trip.  

Plan Your Perfect Oregon Road Trip

Road trips are the best, but they can also be stressful when it comes time to planning them. Crazy as it might seem, but I love planning road trips (my kids make fun of me because I’m always planning our next trip) so if you have any questions about the planning process, please don’t hesitate to ask me in the comments.

How Long Should Your Oregon Road Trip Be

While you could spend months in Oregon and never be bored, I wrote this as a good 10 to 14 day road trip itinerary. It will give you a nice diversity of forest, beaches, and cities.  I’ve also included the campgrounds that we’ve stayed at to make it easier to plan if you like to tent or RV camp.  

Oregon Road Trip: Stick to the Coast or Explore Smith Rock?

A lot of bloggers recommend the Oregon Coast and while yes, I do agree that the beaches along the Oregon coast are beautiful and there are plenty of towns to explore along Highway 101, I prefer the beauty and space along the Columbia River Gorge and the hiking, mountain biking, and climbing in Bend and Smith Rock.  If you can find the time to do both, do it!  

Make Time For Some Off-The-Beaten-Path Adventures

Try some “off the beaten path” activities such as having a bonfire on the beach in Lincoln City, sipping chocolate and petting baby lion cubs in Bandon, holding banana slugs in Coos Bay, and hiring a climbing guide at Smith Rock (unless you climb on your own).  These experiences will give your family memories that will last a lifetime.

How We Plan Our Road Trips

I live for road trips! So much so that our live has become one long road trip with some a little rest and recovery in San Diego along the way. If this is your first road trip or you’d love some tips to make your next road trip super successful, check out these resources:


10 Can’t Miss Stops on Your Oregon Road Trip

We’ve taken many road trips through Oregon. Like I mentioned before, the coast is wonderful and gorgeous, but it’s the inland section of Oregon that really has my heart. These are our favorite spots that we recommend for you to explore in Oregon especially if you to love adventure, hiking, mountain biking, solitude, and rock climbing.

Start Your Oregon Road Trip Itinerary In Portland

Campground: Sauvie Cove RV Park or Thousand Trails

There are so many great things you can do in Portland! And one of our favorite things about Portland (and the entire PNW for that matter) is the abundance of organic and good sourced food.  Find a farmers market to stock up at and if you can time it right, go to the big farmers market on Saturday in downtown (by Portland State University), it’s fantastic!  

While you are downtown, go to Powell’s Books and pick up something to read for while you are lying in your hammock on this trip. 

A trip to downtown Portland wouldn’t be complete without sampling some food from the Food Trucks located between Southwest Alder and Washington streets, from Southwest Ninth to Southwest Tenth avenues. 

If you want to warm up your legs for hiking, take a stroll through Forest Park (mountain biking is also great here).

If you have extra time, check out the Japanese Garden in Washington Park and grab a beer and burger at Mississippi Studios.

When we visit Portland, we camp on Sauvie Island.  Although it isn’t the best campground I’ve been to, it is right on the water and is good enough for on your way in or out of Portland.  We had a great time at the U-pick farms located on Sauvie Island and filled a wagon full of peaches as well as blueberries, raspberries, and loads of veggies.  Note that if you are a Thousand Trails member, then you can camp much closer to Portland.

Portland to Columbia River Gorge

Days Recommended: 1
Miles Driven: 50
Campground: Viento State Park

The 30 miles east of Portland is a forest filled haven with beautiful trails and powerful waterfalls. 

You can do the tourist thing and stop off to take pictures of Multnomah Falls, but we always opt for the less popular, 4 mile round trip hike to Punchbowl Falls via Eagle Creek Trail. If it’s hot out, bring a bathing suit so that you can take a quick dip in the refreshing (read “freezing”) pool of water at the base of the fall.

**Note: After last summer’s fires, many of the gorgeous areas that we visited have been burnt down and trails are currently closed.  

After a long day hiking, we always head to the breweries in Hood River to grab dinner before heading back to Viento campground to the watch gorgeous sunsets over the Columbia River and if you are camping there in the summer, your campsite may be overflowing with ripe blackberries

If you don’t get enough hiking at Punchbowl Falls, you can go into the town of Cascade Falls and hike part of the famous PCT (Pacific Crest Trail) and take a photo by the Bridge of the Gods.  And if you are up for more adventure, head back into Hood River to take a kite surfing lesson.

Columbia River Gorge to Trillium Lake

Days Recommended: 1-2
Miles Driven: 50
Campground: Trillium Lake

Oregon Road Trip Itinerary Trillium Lake
Sunset at Trillium Lake

Trillium Lake is a great stop to get rest and relaxation and disconnect from city life.  The lake itself is small and doesn’t allow motorized boats, but you can swim in the lake, rent kayaks/canoes, or walk the two-mile loop that goes around the lake. 


  • Make sure you have firewood because the campsites have fire rings and star gazing is especially great from this location.   
  • There aren’t many resources here, so stock up before arriving. 
  • This is a great fishing lake. 
  • If you like wine, there are many wineries on the drive up right after you leave Hood River.
  • If you like rock climbing, there is a great climbing area, French’s Dome, that is only a twenty-minute detour and has a super short approach.  It has a couple nice easy routes (5.6 – 5.8) as well as some more challenging routes.  It’s a great area to bring kids to climb and is a good warm up before you get to Smith Rock!

Related blog: Best sport climbing destinations to take kids

Free Camping Bend Oregon
Iconic Smith Rock State Park filled and its perfect climbing walls

Trillium Lake to Smith Rock

Days Recommended: 2
Miles Driven: 100
Campground: Skull Hollow or Tumalo State Park

Smith Rock is a mecca for rock climbing, but don’t let that intimidate you.  There are a lot of routes to choose from and tons of easy climbs if you are just starting out.  There are plenty of guiding services in the area if you aren’t confident climbing on your own.  This is a really great location to try rock climbing for your first time to see if you like the sport.  There is also bouldering here. 

Even if you don’t climb, there are great trails to hike and the scenery here really is striking with the large rock formations and the beautiful blue river running through it with the green trees surrounding the water. 

After a long day of hiking or climbing there is a popular restaurant ten minutes down the road, called Terrebonne Depot, that was good or head into Bend and to try out of the numerous breweries in town.  After dinner, take a nice stroll along the river and finish the day with the best gelato at Bonta (I love the lavender honey flavor!)

Related Bend, Oregon Blogs:

Oregon Road Trip Itinerary Clear Lake
Hiking Clear Lake near Sisters, Oregon

Smith Rock to Sisters

Days Recommended: 1-2
Miles Driven: 25
Campground: Sisters Creekside

Hipster meets rodeo.  That’s what this tiny town of Sisters is like.  This is one of those towns that we stumbled upon and got stuck for a few extra days. 

For starters, the campground is right in town, which always makes if fun to be able to wake up and walk to get coffee or walk to dinner at night.   I love all the deer in people’s yard, the small town feel, and you can sense the community pride you get as you walk through town. 

There are a lot of well marked mountain biking trails for all levels

We used this as a place to get some downtime, relax with a good book, and recover from all our sports at the wonderful yoga studio in town called, Love. Life. Yoga. 

About an hour west of Sisters is one of the most beautiful waterfall hikes we have been on called Sahalie and Koosah Falls.  It’s an easy 2.6-mile loop through old growth forest.  There are so many amazing short hikes in this area.  

Related Blog: 5 Adventures you must do on the Mackenzie River 

Oregon Road Trip Itinerary Crater Lake
View looking down on Crater Lake

Sisters to Crater Lake

Days Recommended: 1
Miles Driven: 150
Campground: Mazama Campground in Crater Lake National Park

It took us a long time to finally squeeze in Crater Lake on our Oregon road trips and when we finally made it there I couldn’t believe that we had skipped it so many times.  It is gorgeous.  While we didn’t stay overnight because we wanted to go bike the Peter Skene Ogden trail (which is a great detour between Bend to Crater Lake), it is certainly worth spending a full day hiking or biking here.   

Related Blog: Mountain Bike or Hike the Peter Skene Ogden Trail 

Oregon Road Trip Itinerary Coos Bay
Look at the size of that sea star!

Crater Lake to Coos Bay

Days Recommended: 2
Miles Driven: 180
Campground: Sunset Bay State Park

Coos Bay is an ecological wonderland and there is a nice campground that sits in the middle of it.  There are hiking trails, beaches, and whale watching. You can hike right from the campground through pristine coastal forest to Shore Acres and Cape Arago State Park.  You will get incredible ocean views along the way.   Cape Arago is a wonderful place for whale watching year round, but especially great in the winter.  The nature centers do a great job of engaging kids and having interactive presentations.  There’s a nice bay for kids to play in right across the street from the campground.

We absolutely loved Bandon!  Besides combing the beach for unique and beautiful seashells, the store Coastal Mist has the most amazing chocolate!  And you have to stop at West Coast Game Park Safari where we got to pet a baby lion, tiger, and bear as well as see many other animals up close.

Oregon Road Trip Itinerary drift creek falls
View above Drift Creek Falls

Coos Bay to Lincoln City

Days Recommended: 2
Miles Driven: 180
Campground: Devil’s Lake State Recreation Area

There are a lot of great hiking opportunities near Lincoln City such as Drift Creek Falls, Valley of the Giants, and God’s Thumb.  

It’s a bit of a detour, but mountain biking Black Rock Mountain has been on our bucket list of adventures.

On the way up to Lincoln City from Coos Bay, stop in Reedsport and rent quads or dune buggies and go play in the sand dunes.  We didn’t get a chance to have a campfire on the beach here, but we so wish that we did!  Glass blowing tours are also popular to do in town.  

Tip: Driving highway 101 can be slow so account for this on the way up.

Oregon Road Trip Itinerary Devil's Churn
Make sure to stop at Devil’s Churn on your road trip

Lincoln City to Cannon Beach

Days Recommended: 1-3
Miles Driven: 100 miles
Campground: Fort Stevens State Park

We love Cannon Beach and not just because it is one of the ten most beautiful beaches on the west coast.  We love it’s quaint downtown area, it’s great food, and it’s laid back vibe.  

Make sure to check out Hay Stack Rock and go tide pooling for sticky anemone. 

We love the bread at Sea Level Bakery, the coffee at Sleepy Monk Coffee Roasters, the crepes at Crepe Neptune, and the specialty foods at EVOO, where you can even sign up for cooking lessons. 

If you have time, head up to Seaside Beach and catch some waves or go for a run and get distracted picking all the blackberries that grow along the road. 

Staying a few nights at Fort Stevens will give you a little rest and relaxation to finish off your road trip.  This huge campground has miles of paths for running and biking as well as nice beaches to play at during the day.  We have also stayed at Newhalen State Beach and enjoyed camping right by the beach.

What are your favorite places on an Oregon Road Trip? Let us know in the comments and let us know if you have any questions!

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Mihika Iyer

Tuesday 22nd of October 2019

Oregon is in my wish list due to beautiful canyons and volcanic fields. You have taken a beautiful road trip alongg the Oregon eastern side. I loved the pictures of Painted Hills.

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