Road trips are as much about the journey as they are about the destination (or destinations, as the case may be.) If you’re in the mood for some small-town charm and scenic views, I have an itinerary for you that has it all. These five small towns in Oregon are lovely destinations, each with something special to offer, and you’ll enjoy some stunning natural beauty along the way.

The route takes us almost from the border of California up to the border of Washington, about 385 miles. Some of the towns on our route are close enough to visit on the same day, but I’ve included a great place to stay in each of them so you can slow down and explore. Click on the map to customize your trip (you can even do it in reverse if you like!)

It seems fitting that we start at the beginning, well sort of. We’ll begin by visiting one of the state’s most historic towns and a National Historic Landmark, Jacksonville. Established during Oregon’s gold rush, there is an abundance of well-preserved history here, including more than 100 historic buildings. As you explore the town, the architecture will sweep you back in time to the 1800s.

This also happens to be a town known for its awesome antiquing, alongside lots of other cool shops and boutiques. You can spend the night at Jacksonville Inn which was built in 1861. Don’t worry, the rooms are beautifully updated, and you can enjoy a wonderful wine country-inspired meal at the hotel’s restaurant.

Next, we head north to Oregon’s “Covered Bridge Capital of the West,” Cottage Grove. It has been called one of the most charming towns in the U.S. In addition to six beautiful historic covered bridges in and around the town, Cottage Grove is known for its scenic nature and outdoor activities. In fact, one of the best ways to explore is by cycling along the Covered Bridges Scenic Bikeway, which lets you experience all six bridges, lush foliage and flowers, picturesque views of Dorena Lake and Culp Creek, and the historic downtown. Of course, you can explore all or part of the trail.

In town, consider a meal and drinks at Coast Fork Brewing. There are quite a few rentals around town where you can get a good night’s sleep, such as this charming guest cottage near downtown.

From Cottage Grove, we go west to the beach and the tiny town of Florence. It may be small, but this coastal community has a lot to offer despite flying under the radar as far as tourism goes. Enjoy a tranquil day exploring sights like Heceta Head Lighthouse, with its stunning views that may include migrating whales, the historic Siuslaw River Bridge, and the Sea Lion Caves.

The town’s walkable Historic Old Town is filled with quaint shops, galleries, a museum, delicious food and drink, and warm, friendly people. At the end of the day, enjoy a delicious dinner in a historic train station overlooking the river at the Waterfront Depot Restaurant. Then, tuck yourself in for the night at the charming Edwin K Bed and Breakfast. You’ll feast on a cooked-to-order breakfast before the drive to our next town.

A scenic drive along our gorgeous coast will bring us to Cannon Beach up north. Unlike Florence, this is a very popular destination, and for good reason. Graceful sand dunes, scenic rivers, and — according to National Geographic in 2013 — one of the most picturesque beaches in the world make this a must-visit small town. The beach itself, with its famous Haystack Rock, colorful birds, and vibrant tidepools is the star of the show. From late spring through the end of summer, you can even enjoy horseback riding on the beach.

Away from the sand, downtown Cannon Beach is a sweet little town worth exploring. You’ll discover cute little retail boutiques, coffee, candy shops, and delicious restaurants, from pizza to seafood to breweries. If seafood happens to be your craving, grab a seat at Anna’s Table for a classic PNW meal. For an unforgettable overnight stay, enjoy the sunset from the deck of a cozy beachfront cottage. 

I may be partial, but I think one of the coolest fun facts about our last stop is that the movie "The Goonies" was set and filmed there. In fact, you can see filming locations all over the town of Astoria. Visit the historic County Jail (now the Oregon Film Museum) and you’ll be able to see the cell used in the movie and even the family’s jeep outside. In addition to famous scenes from the movie, Astoria has some incredible historic buildings you’ll want to check out such as the Liberty Theater and the Queen Anne-style Flavel Mansion. When you’ve worked up an appetite, make your way to Fedé Trattoria for fresh traditional Italian cuisine on the waterfront. It's a perfect way to end our small-town road trip. 

Are you ready to begin your West Coast adventure? Grab the keys, share this article with your travel partner, and let’s go! Of course, there are far more than five worthy little destinations in our awesome state. Check out more of our favorite small towns in Oregon for some inspiration.