Here in Oregon, the wanderlust is real. There are simply so many places to see and explore, and there’s no better way to do this than a road trip! If you’ve ever wanted to explore some of Oregon’s most charming small towns, we have just the road trip for you. One of the best road trips in Oregon, this scenic adventure will lead you all along the Oregon Coast, through the Willamette National Forest, all the way to lovely Jacksonville, stopping by some of the most charming small towns in Oregon along the way. Fuel up the car, and let’s go!

Looking for one of the best road trips in Oregon? It's right here!
google maps
When it's all said and done, this road trip clocks in with 14 hours of drive time, and the journey can take as many days and nights as you'd like. Check out the customizable Google Map here. Let's go!
1. Vernonia
flickr/ Robert Ashworth
The first stop on the trip is Vernonia, a lovely little town in northwest Oregon. This scenic town has tons of charm, natural beauty, and history. Be sure to check out Vernonia Lake Park, where you can explore an incredible abandoned mill!
2. Astoria
flickr/ Granger Meador
The next stop on the road trip is the beautiful, historic town of Astoria. This historic town is the oldest U.S. settlement in Oregon (and the entire West Coast), and to this day it’s full of fascinating historical points of interest as well as unique modern amenities and beautiful scenery. The town is located at the mouth of the Columbia River, and is full of wonderful shops, restaurants, museums, hotels, and more.
3. Cannon Beach
flickr/ Snapmann
Driving down the coast, you'll find many beautiful beaches, hikes, and small towns. One fabulous small town is Cannon Beach, widely regarded as one of the most beautiful places in the world. Cannon Beach is home to the iconic Haystack Rock as well as many great restaurants, galleries, shops, and pubs. Cannon Beach has a population of 1,691.
4. Depoe Bay
flickr/ Sheila Sund
Choosing between the many charming towns on the coast of Oregon is not a simple task! We recommend pulling over anywhere that catches your eye. One place that's definitely worth a visit is the tiny town of Depoe Bay, which is home to some absolutely amazing restaurants like Tidal Raves and Restaurant Beck, as well as the smallest navigable harbor in the world.

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5. Yachats
flickr/ Al Case
Continuing south along the coast, you'll come across the beautiful town of Yachats. This quaint fishing village (home to just 550 full-time residents!) is positively enchanting. There are some great restaurants and unique places to stay the night, including the nearby Heceta Head Lighthouse, where you can spend the night in the historic lightkeeper's house bed and breakfast. Charming coastal vibes, spectacular natural wonders, an abundance of outdoor recreation, and an amazing cultural scene — Yachats, Oregon is peak PNW living!
6. Florence
flickr/Stephanie Sarles
For the final stop on the coast, visit the magical town of Florence. This incredible town is full of character and breathtaking beauty, and it's a wonderful place to visit year round.
7. Drain
flickr/ Bruce Fingerhood
Heading inland, you'll pass through the town of Drain. Silly name aside, this unique place is full of historic buildings and pretty scenery.
8. Cottage Grove
flickr/ Doug Kerr
Cottage Grove isn't as small as some of the other towns mentioned, although it is packed full of charm. One great activity is checking out the Cottage Grove Covered Bridge Tour (a self-guided biking or driving loop) to see why Cottage Grove is called the Covered Bridge Capitol of the West!
9. Sisters
flickr/ Jonathan
Surrounded by stunning scenery, Sisters is a charming, outdoorsy town that's home to lots of great local shops, galleries, cafes, inns, and even two spas. The town also hosts several fun annual events, including a rodeo, a folk festival, and a quilt festival.
10. Jacksonville
flickr/Stephanie Sarles
Last but not least, you'll reach the old gold mining town of Jacksonville, Oregon. This incredible town is full of history -- in fact, the entire downtown district is listed as a National Historic Landmark. You'll want to spend some time wandering through the town and exploring the local shops, cafes, and museums. There are some great B&Bs where you can stay the night, or you can book a room in the historic Jacksonville Inn.

Do you enjoy Oregon’s small towns as much as we do? Each and every one of these winsome little locales makes for an amazing day trip adventure!

For more of the best road trips in Oregon, check out these bucket-list-worthy adventures.

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More to Explore

Best road trips in Oregon

Sarah | August 10, 2021

What are some bucket-list-worthy road trips in Oregon?

There are few better ways to experience the unique wonders of Oregon than by taking a road trip through the state. We know this, which is why we are always putting together epic Oregon road trip adventures! From chasing waterfalls to touring the state’s most delicious restaurants, here are eight of the best road trips in Oregon you can take for truly unforgettable experiences. Spoiler alert: our Natural Wonders Road Trip is absolutely one you need to add to your Oregon bucket list. On this trip you’ll visit the deepest lake in the country, the summit of a mountain, Oregon’s Painted Hills, and more — all in one of the most unforgettable scenic road trips in Oregon. Could there be anything better?

What's the best small town in Oregon?

In addition to each and every one of the small towns listed above, definitely add Silverton to your list of charming Oregon towns. Known as Oregon’s Garden City, Silverton is home to an abundance of beauty, everywhere you turn. Truly -- head out in any direction from Silverton's main square, and you’ll encounter something splendid: a roaring waterfall, magical garden, covered bridge, or quaint landmark. It’s such a joy to be in Silverton, which, in our humble opinion, is quite possibly the best place in Oregon!

What are the best day trips I can take in Oregon?

While we're all for big road trip adventures, sometimes you just have an afternoon to spare. And in those instances, a day trip is perfect. We've compiled 13 of our favorite Oregon day trips in this article; noteworthy attractions include Crater Lake, Smith Rock State Park, Bagby Hot Springs, Shaniko (an Oregon ghost town!), and even a coastal drive on Oregon's Highway 101. If you're searching for more outdoor places to explore, we just love spending the day at Wallowa Lake. And if you're craving all.the.donuts, you can visit six of the best donut shops in Oregon on this fun (and delicious!) day trip we put together!

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Featured Addresses
Vernonia, OR 97064, USA
Astoria, OR 97103, USA
Cannon Beach, OR, USA
Depoe Bay, OR 97341, USA
Yachats, OR, USA
Florence, KY, USA
Drain, OR, USA
Cottage Grove, OR 97424, USA
Sisters, OR 97759, USA
Jacksonville, OR 97530, USA