Not known for its massive bustling big cities, Oregon instead has miles of coastline, vast forests, tall mountains, beautiful deserts, and charming small towns.
The activities, good food, and local wine are never-ending, all with picture-perfect backdrops no matter where visitors end up. The best way to explore this beautiful outdoors is to visit the best small towns in Oregon.
Some links in this post may be affiliate links. If you make a purchase through one of these links, we may earn a small commission at no extra cost to you. Please see our disclosure policy for more detail.
This fishing village is the oldest settlement west of the Rocky Mountains and since then has grown into being one of the quaintest coastal towns in Oregon.
The Victorian-style homes overlook the Columbia River and are gorgeous to look at while exploring local breweries. The many forts and museums are also worth checking out and great seafood is available when it’s time to sit down for a rest.
Brownsville is the perfect spot for history buffs and movie lovers as this truly small Oregon town has kept most of its original buildings, or at least the original style.
Movie fanatics may know this spot from the film Stand by Me as it was shot here. The surrounding landscape completes this amazing and beautiful getaway.
Almost constantant winds through the Columbia Gorge creates the perfect spot for wind sports. Most notably windsurfing, as Hood River has become known as the windsurfing capital of the world.
Along with other outdoor activities in the area including hiking and skiing, this is the perfect spot to visit for its proximity to Mount Hood and the Columbia River.
Located on some of the most photographed scenery in Oregon, this little town is home to a handful of stores and a breathtaking beach backdrop. Seven miles of sandy beach, in fact!
There is little more than a grocery store, book stores, and a few dining options, but it is all still worth checking out as Manzanita is quiet and peaceful.
If you’d like to escape the city, Manzanita is among the best day trips from Portland!
Six covered bridges are located in this little town, making it the covered bridge capital of the west. These beautiful bridges are something rarely seen west of the Mississippi River.
Hiking, biking, and horseback riding are also available in the area. The downtown area has many historic buildings and fantastic shopping such as galleries, cafes, and stores.
At the entrance to the Columbia Gorge, this beautiful town is perfect for a stroll and to explore all the little shops and restaurants. The buildings are beautifully historic as the town captures its history in the many murals painted on the downtown buildings.
Since it is located on the east side of Mount Hood, the sun is almost always shinning, creating a beautiful and relaxing experience.
Established in 1899, this once rugged logging town has blossomed into a perfect and beautiful small town in Oregon to visit.
There are also a variety of cheesemakers and chocolatiers available to taste local treats and to take some home. A surprising amount of tasting rooms are available to choose from within only a few blocks.
This slightly larger town is situated right on one of the most well know stretches of beach in Oregon of the same name.
Visitors come from all over for walking, hiking, biking, and photo opportunities, and Cannon Beach is an essential stop on a coastal Oregon road trip.
The tide pools are especially interesting as there is always a volunteer there to keep the nature sight protected and provide interesting information.
Be aware that weather on the coast can be unpredictable with foggy, chilly weather one day and sunny, warm weather the next.
Nestled among Oregon sand dunes and on the coast, this town is so small that it doesn’t have any traffic lights.
But this doesn’t mean there is nothing here to enjoy; antique shops, restaurants, and an art gallery make up the little storefronts. The food here is classic northwestern and well made.
Surrounding the town, the dunes offer the chance for some exciting sports, including four-wheeling. The nearby beach is the perfect spot to build a sandcastle or soak up some sun.
Most will know this name as the dairy brand for milk, cheese, and ice-cream. It’s also the name of one of the prettiest small towns in Oregon, where the company’s headquarters and factory are located.
The town is cute with good food and shopping, but the biggest attraction is the factory. Great cheese and ice-cream are available in the store and are from the cows you see out in the nearby fields.
Tours of the factory also show how the dairy is processed creating a fun-filled day for everyone.
This spot is for the Pinot-Noir lovers as this little town is right in the heart of the Willamette Valley and tasting rooms are in abundance for wine and beer.
Many little shops including boutiques, cafes, and farm-to-table dining line the historic downtown for a peaceful experience.
For something a little more out there, the town also has a space museum, you’ll know it by the Boeing 747 resting on top. Bring a swimsuit as a water slide is housed inside the large building. The annual UFO festival is also a must-do.
Situated near the Three Sisters mountain peaks, this western-style town is a must-stop if visiting the area.
While most visit for hiking, skiing, fishing, or camping, most don’t know they can end the day with a bit of shopping and a soak in a beer spa.
This historic little town has kept its old gold-rush era architecture, creating a beautiful atmosphere for the multiple tasting rooms and shops that make up one of the best small towns in Oregon.
The most popular attraction though is the yearly summer outdoor concerts held here called Britt Fest that has attracted some big-name performers in the past.
Known for its 10 waterfalls within easy access of the town limits, there is also a large botanical garden and a historic Oregon White Oak tree the town was originally built around.
The town itself captures its history through many beautiful murals, see how many you can spot while exploring the shops. Silver Falls State Park is also nearby for the outdoor adventurous types.
The beautiful Oregon town of Enterprise is the perfect stopping point while heading out to explore the nearby Hells Canyon, one of the earths deepest gorges.
The town itself is home to many pieces of art made out of bronze, becoming a center for bronze art. A historic lodge, out on Wallowa Lake is the perfect spot for a peaceful overnight or extended stay.
Pendleton is known for its textiles, so be sure to pick up some local shirts or blankets while in town.
This is also the perfect spot for experiencing a bit of the wild west as traditional rodeo events happen often.
The biggest attraction is the yearly events such as the Pendleton Round-up, parades, and the Pow Wow Dance Competition.
Yachats, Oregon is highly interesting for its geographic wonders surrounding it.
Devils Turn is to the north, an inlet carved by years and years of waves crashing into soft rock. To the south is Thor’s Well, a massive hole that swallows sea water into the deep abyss.
Within the town, cute hotel options are available for longer stays, and art galleries are dotted throughout.
Life size bronze statues line the walkways as you explore the galleries, shops, and restaurants of Joseph, one of the most beautiful towns in Oregon.
Many nearby lakes, mountains, and canyons make this a perfect spot to explore nature from.
A cute little town in Oregon, Florence is often a stop on the way to play in the nearby sand dunes of the Oregon Dunes National Recreation Area.
It is also near the coast, therefore Sea Lion Caves, beachfront, and a lighthouse are nearby for a day full of fun activities. Many great shops and restaurants line the streets for a more relaxing option.
The endpoint for many people who traveled along the Oregon Trail is now a travel destination for history buffs.
Museums house artifacts and replica wagons, the type of wagons that made the authentic ruts outside the museum.
The beautiful scenery surrounding the town is perfect for photos or for the outdoor adventure type.
Grants Pass is a popular spot as it’s known as the state’s whitewater rafting capital due to Rogue River that runs right through town.
After an exciting day on the water, the historic downtown offers a number of activities including a soda fountain and a live theater.
Newport bit larger than some of the cute small towns in Oregon rounded up here, but well worth the stop as the Oregon Coast Aquarium features underwater walkways and a seabird aviary.
Other great stops are the Yaquina Bay Bridge and the Yaquina Head Lighthouse. The town also has wonderful seafood and shops along its downtown area.
Near California, this quaint Oregon town is best known for its annual Oregon Shakespeare Festival that has been running for over 80 years.
If the festival is not around, multiple theaters, restaurants, and shopping is available for entertainment.
The town also sits at the base of the Siskiyou and Cascade mountain ranges, offering many outdoor activities including hiking, biking, camping, and horseback riding.
A perfect spot for a quiet getaway as this sleepy town is relaxing without sacrificing things to do.
Here there is a golf course, boat tours, and an ice-skating rink. Beautiful hiking and biking are also available in the area for more peace and quiet.
This little town, surprisingly walkable and bike friendly, is tucked away in the basalt cliffs along the Columbia Gorge.
The surrounding area offers unique hiking and biking trails with rewarding views of the cliffs and surrounding areas.
The town itself has some great food options and tasting, both wine and cider, and the variety and number of things to do make it one of the best small towns in Oregon!
You May Also Like…
Washington: 25 Best Small Towns in Washington
Crater Lake: 15 Best Crater Lake Hikes (For All Skill Levels!)