The 15 Best Small Towns in Oregon to Visit This Year

Have you been to Oregon yet? You need to. It’s an amazing state full of beautiful scenery and tons of great cities and areas to explore. This article is going to walk you through 15 of the best small towns in Oregon to visit!

While a lot of people head to the Oregon Coast (you should too!) there are also some great, lesser-known towns to visit as well.

Oregon’s biggest and most popular city is Portland, which is amazing and with a lot of unique and weird things to do. I mean, did you even go to Oregon if you didn’t stop by Portland and fill up on donuts, craft beer, and coffee? Exploring the interesting historical and quirky neighborhoods in Portland is a must!

But, there is so much more to this state and there are so many things to do in Oregon! Checking out the Oregon small towns is a really fun and unique way to make the most of your trip.

I’ve been to Oregon a few times and visited Portland and the Oregon Coast, including the unmissable Cannon Beach. While I haven’t been to all the cities on the list, I do know first-hand just how awesome this state is and how great it is to explore!

I’m getting excited for my next Oregon trip just by researching this article! 

The 15 best Oregon small towns

Are you ready to start on the small Oregon town tour? We’re going to cover a lot of ground here, from small towns near Portland, to the northern towns along the Columbia River, in the eastern and southern regions of Oregon, and of course, small towns on the Oregon coast.

1. Forest Grove

Forest Grove is a small town near Portland, about 25 miles west of the city. It’s known as a former farm town, but now is a suburb of the greater Portland area where many people commute to work. It was actually the first city incorporated in the County, though, back in 1872! 

There are a few things to do in Forest Grove, including:

• Check out and explore the historic city center, including the heritage districts with colonial-style homes.
• Get outside and go bird-watching at the Fernhill Wetlands.
• Check out the Banks-Veronica State Trail, which used to be a rail line and is now a paved bike and walking trail.

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2. Dundee

Dundee is a tiny town – just over 3,000 residents live here! It’s a very small area, just 1.36 square miles big, and is located 25 miles southwest of Portland. It’s a great small town in Oregon to check out. 

It was established back in 1881 and was part of the Oregon railway network. Today, it’s best known as wine country!

It has a ton of beautiful vineyards to tour, relax, and sample some wine at – a perfect way to spend the day! Here are some things to do in Dundee, Oregon:

• Check out some wineries! There are so many to choose from, but some of the most popular are Sokol Blosser Winery and Argyle Winery. You’ll love spending a relaxing day sipping on some local wine and enjoying the beautiful views out over the vineyards. 
• Visit the Red Hills Market or the Briar Rose Creamery to pick up some delicious local food and drink in the area.   

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3. Boring

I have to admit, this small town in Oregon was included simply because of its name! How can you not want to check out a place called Boring? Luckily, Boring is not boring, but actually has a log of cool things to see and do. 

Boring is located about 12 miles from Portland, so it’s easy to visit for a quick day trip. It was named after a pioneer named William Harrison Boring, who likely didn’t think his last name would end up as a fun attraction for visitors!

Fun fact: Boring, Oregon is a sister city to Dull, Scotland. In fact, there is even a day each year (August 9th) to recognize the partnership between these cities. Make sure to celebrate Boring & Dull Day if you’re in the area!

Here are some of the best (not boring) things to do in Boring:

• Check out Liepold Farms and pick up some local seasonal produce. In the fall, they have a pumpkin patch and corn maze! It’s a great place to bring the family and have some fun.
• Grab a bite to eat at The Not So Boring Bar and Grill. 
• Snap some pictures of Mt. Hood, which is visible from many areas around Boring. Mt. Hood is 11,000 feet tall, so the views are pretty epic!

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4. Hood River

Despite being named after the nearby Hood River, this small port town is actually located along the Columbia River in northern Oregon. It’s one of the prettiest towns in Oregon, with views of Mt. Hood and close to the Columbia River Gorge.

Hood River is a nature lover’s paradise! Thanks to its mild climate and lower amounts of rain than other parts of the state, visitors can enjoy all sorts of fun outdoor recreation activities. 

Here are some fun things to do in Hood River, Oregon:

• Golf at the beautiful Indian Creek Golf Course. It’s located right in the foothills of Mt. Hood and has great scenery to enjoy while playing a round of golf.

• Pick up some local food and drink from the Hood River Farmers Market. It’s a great place to try some delicious meat, cheese, baked goods, and more!

• Take in the sights and smells at the Lavender Valley Farm. Rows upon rows of beautiful purple lavender are available to tour and take pictures in. There is also a shop selling amazing lavender products!

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5. Astoria

Astoria is one of the more historic towns in Oregon and is located in the northern region along the Columbia River. It’s a port city that marks the border of Oregon with its neighbor, Washington, which is just across the bridge. 

Astoria was established back in 1876 and was an important port city for the fur trade. Today, it’s a cool and quirky city where you can visit some of the interesting historical sites but also explore the fun different places to eat, drink, and shop!

Here are some fun things to do in Astoria, Oregon:

• Check out the Astoria Column, a 125-foot monument to the original explorers and founders of the city. There are amazing views over the city and the river at the monument.

• Visit an old shipwreck at Fort Stevens State Park. Located on the beach at Fort Stevens Park is the wreck of Peter Iredale, which ran ashore back in 1906!

• Take a ride on the Astoria Riverfront Trolley. You’ll learn more about the city and get some cool views from this historic waterfront trolley ride.

• Eat some fresh-caught fish! Many restaurants have catch-of-the-day deals, so you can try some fresh fish. Check out Silver Salmon Grille or Bowpicker Fish & Chips.

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6. Pendleton

Pendleton is located in the northeast region of Oregon, one of the many small towns along the Columbia River. It is known primarily for the Pendelton Woolen Mills which makes fine woolen goods like blankets and shirts. 

Besides the reputation for fine wool goods, Pendleton is also known for its rodeo! In fact, the western spirit is alive and well in this town, and was named a Top 10 western town in the True West magazine! 

Here are some of the most fun things to do in Pendelton:

• Take a drive and visit Hat Rock, Walla Walla, and Wheatfield. This scenic 120-mile drive will take you along the Columbia River into the Walla Walla Valley. It’s super scenic and has some great stops along the way. You can follow this itinerary. 

• Visit the Pendleton Center for the Arts. Admission is free, and it’s a great place to express your creativity by taking a class, checking out live music, or browsing the art galleries.

• Go on an underground tour and learn more about this historic town in Oregon, Pendleton, and the old red-light district. You’ll be fascinated by the stories that include bootlegging, gambling, and all other nefarious activities!

• Channel your inner cowboy and pick up a hat at Montana Peaks Hat Company. They even do custom designs!

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7. Baker City

Baker City is located in the eastern region of the state, close to the border with Idaho, and is known as the “base camp” for Eastern Oregon. As such, there are a lot of great things to do and see in this Oregon small town. 

It has a very quaint downtown area to explore but is best known for its historical and heritage attractions. You can learn more about the Oregon Trail and other pieces of history in this region. There is also a lively city center with great places to eat, drink, and shop. 

Here are some of the best things to do in Baker City, Oregon:

• Go skiing or snowboarding at the nearby Anthony Lakes Mountain Resort.

• Explore the Oregon Trail. Immerse yourself in history from 150 years ago when pioneers moved out west into Oregon, exploring and settling the region. 

• Experience some luxury at the Geiser Grand Hotel. This iconic hotel is a landmark in Baker City and is the epitome of luxury with crystal chandeliers, stained glass ceilings, beautiful artwork, and incredible food. Stay there if you’re looking for a splurge, or just visit for a bit!

• Grab a beer at Barley Brown’s. Established in 1998, it’s one of the best-known breweries in eastern Oregon. Watch out Portland, eastern Oregon is coming for you!

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8. Joseph

Joseph is a small Oregon town located about 110 miles north of Baker City, in the northeast corner of the state. It is known for its gorgeous natural beauty because it’s settled right in the foothills of the Wallowa mountain range. Because of the amazing alpine views, it’s earned the nickname “Little Switzerland of America”!

Joseph is a great place to go if you enjoy getting outside and being active, as it has a ton of outdoor recreation opportunities. The town itself is also known as an artistic town with lots of galleries to check out. If you like to eat and drink delicious local products, this is the place to go!

Here are some of the best things to do in Joseph, Oregon:

• Visit Wallowa Lake State Park and spend the day hiking, walking, kayaking, boating, or fishing. There is so much to do here! You can also camp overnight in the RV and tent camping area, or in a yurt or cabin.

• Catch a view from the Wallowa Lake Tramway. If this place truly is the “Little Switzerland of America” then the best way to experience it is from up high on a tram car. It will take about 15 minutes to climb the 3700-foot ascent to the top. You’ll want to bring a camera to snap some pics and remember those gorgeous views.

• Unleash your inner artist at the Josephy Center for Arts and Culture. Here you can check out the rotating exhibits or take a class and make some art for yourself.

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9. Jacksonville

Heading down south in Oregon is Jacksonville, a small town named after the Jackson Creek. The area is famous as one of the first areas they found gold!

Today it is home to less than 5,000 residents, making it truly one of the smallest towns in Oregon. It is located in the southwest region of Oregon.

Besides being famous as a historic Gold Rush town, Jacksonville is also popular for the Britt Music & Arts Festival which happens all summer long.

This, along with great outdoor recreation, plenty of local eateries, and delicious wineries make Jacksonville a great place to visit!

Here are some of the best things to do in Jacksonville, Oregon:

• Check out some live music at the Britt Music & Arts Festival. This is one of the most popular festivals in the summertime and has been operating since the 1960s. It has a capacity of 2,200 people and many popular artists headline each year.

• Hike, bike, or horseback ride in Forest Park, a large, 1,100-acre park with tons of different trails to check out. There are even remnants of old gold mines spotted throughout the park!

• Learn some local history on a Jacksonville Trolley Tour. You’ll visit some beautiful vintage homes and buildings and learn more about the history of this once-booming gold rush town.

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10. Klamath Falls

If you head to the southeast region of Oregon, you need to make a stop at Klamath Falls. It’s located on the shore of the beautiful Upper Klamath Lake and is only 25 miles from the California border.

It was once a logging industry town but is now known as an enjoyable outdoors town with over 300 days of sunshine each year!

Klamath Falls is also known for its proximity to Crater Lake and Mt. Shasta, regions of the state that attract many year-round visitors to see the gorgeous scenery. 

Here are some of the top things to do in Klamath Falls, Oregon: 

• Visit Moore Park. This is a beautiful city park that is popular with the local residents. It’s a great place to go for a walk, run, or hike the many trails. There are also a number of sports venues, courts, picnic areas, and a concession building.

• Check out the waterfalls. Contrary to popular belief, there is no actual Klamath Falls. There is another set of waterfalls called Link River Falls, named for the town’s original name of Linkville. You can hike to these stunning 115-foot falls and enjoy the sites!

• Go for a road trip and visit Crater Lake. Located 60 miles away from Klamath Falls is the most beautiful and unique spot in all of Oregon, arguably. Crater Lake is a lake made from, well, a crater! It’s a collapsed volcano from 1000s of years ago, now a picturesque lake. 

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11. Ashland

Ashland, Oregon holds the prestigious place in the top ten of “The 100 Best Small Art Towns in America.” It’s known for the Oregon Shakespeare Festival and other arts and cultural events such as galleries and theaters. 

This small Oregon town is located in southern Oregon, just a few miles away from California.

Here are the best things to do in Ashland, Oregon:

• Catch a show at the Oregon Shakespeare Festival. This festival runs from February to November every year and brings 10 of Shakespeare’s famous plays to life. You are bound to find something you love, whether you go to one or all of them!

• Go skiing at Mt. Ashland. This amazing ski and snowboard area was actually in danger of going out of business, but the community stepped in and saved the day! It has 200 acres of terrain to explore, so get out there and enjoy!

• Visit the beautiful Rogue River. There are a number of recreational sites along the river and some fun adventures like river rafting are available!

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12. Cottage Grove

Cottage Grove is a small town in Oregon that is located just 22 miles south of Eugene, in the central region of the state. It is known as the covered bridge capital of Oregon and is a quaint, bike-friendly town. 

Here are some of the best things to do in Cottage Grove, Oregon:

• Bike along the Covered Bridges Scenic Bikeway. There is a 37.8-mile bike trail that will lead you through tons of picturesque covered bridges. Spend a day out in nature and enjoy this area!

• Enjoy a day outside at Dorena Lake. This area is very picturesque with rolling hillsides. The lake is perfect for swimming, boating, and fishing. 

• Take a walk around town and visit the murals of Cottage Grove. There are 21 murals around town that show different aspects of the history of this town. It’s a great way to explore the area and learn more about it. 

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13. Cannon Beach

Cannon Beach is one of the most popular small towns in Oregon and is known for its famous Haystack Rock. The town is located along the Oregon coast in the northern region. It is a laid-back beach town with lots to see and do and attracts many visitors every single year. 

Here are some of the best things to do in Cannon Beach:

• Enjoy the beach! Cannon Beach is very long, so it’s the perfect place to go for a long walk and take in the sites. Haystack Rock is a large rock in the middle of the beach that makes for a beautiful landscape and is iconic to the area.

• Go shopping! Cannon Beach town has so many cute little shops to explore. You can find local handicrafts to unique fashion stores to specialty candy stores. 

• Visit art galleries. There are a number of beautiful art galleries in this Oregon small town, so make sure you spend some time looking around and checking them out.

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14. Yachats

Yachats is another coastal small town in Oregon, located in the central region of the state. It’s named after the Yachats River and is a popular destination for outdoor activities like beachcombing or hiking at the beautiful Cape Perpetua Scenic Area.

The town of Yachats has great shops, restaurants, and art galleries to check out, too!

Here are some of the top things to do in Yachats, Oregon:

• Marvel at the beauty of Cape Perpetua Scenic Area. This is the highest point of the Oregon Coast and offers absolutely stunning views from every point. Take some time to explore the various trails here.

• Eat some seafood! There are so many great options in Yachats since it is a coastal town, but you can’t go wrong with some good old fish and chips from Luna Sea Fish House.

• Go for a spa day at Overleaf Lodge and Spa. Since there are so many outdoor activities to stay busy within Yachats, you might need somewhere to get a little R&R. Go for a massage and just bliss out here for an afternoon!

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15. Florence

Florence Oregon is just a short drive south from Yachats along the Oregon Coast. It is referred to as “Oregon’s Coastal Playground” because of its miles and miles of rolling sand dunes. You can truly enjoy the coastal experience here!

Here are some of the best things to do in Florence, Oregon:

• Enjoy the sand dunes! You can go horseback riding, sand dune buggying, sandboarding, or just walk around and enjoy the miles and miles of sand.

• Visit some sea lions. Florence is home to many sea lions, so you can go to the Sea Lion Cave along Highway 1010 to see these amazing creatures.

• Go whale watching! Sea Lions aren’t the only animals in this town. Join a boat tour to go see some whales up close.

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Best time to visit Oregon  

Oregon is a great year-round destination. The best time to visit Oregon is usually the summer months (June to September) when it is warm and dry. This is the time of year you can enjoy all of the amazing Oregon Coast beaches, like Cannon Beach! 

But it’s also fun to travel to Oregon during the other seasons, too. It can be really cool to check out the Oregon Coast when it’s moody and overcast, or you can just head to some of the small towns in Oregon and check out some indoor activities!

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