What Are The Best Small Towns To Live In In Oregon?

May 03, 2023 By Sean William

Oregon is known for its ruggedly beautiful outdoor spaces, but its small towns are just as charming. From the lush vineyards of Willamette Valley to the majestic mountain passes near Bend to the cozy coastal hamlets between Astoria and Brookings, Oregon offers a wealth of wonderful small-town options that offer something for everyone.

Whether you’re looking for historic charm and culture in towns like Ashland and Carbon or want adventure in areas like Umatilla, Oregon has plenty of great small towns to explore.

In this blog post, we’ll highlight some of the best small towns in Oregon – from up-and-coming wine regions to rustic recreation spots – so come along with us on a journey through these special places where history meets nature!

Overview of Oregon's Best Small Towns and What They Have to Offer

Oregon is a stunning destination for travelers looking to experience the beauty of the Pacific Northwest. Aside from its famous cities, Oregon also boasts an array of small towns with big characters perfect for getting away from it all.

From organic wineries and restaurants to adventure treks in national parks, there’s something for everyone in these best small towns in Oregon.

Hood River

Located in the beautiful Columbia River Gorge, Hood River is a popular destination for hikers, mountain bikers, and windsurfers. But this small town has much more to offer than its outdoor activities.

With its charming downtown full of independent shops and galleries, Hood River is a great option for anyone looking for a relaxing getaway.

If you’re in the area, visit the family-owned Hood River Organic Winery to sample some of Oregon’s finest wines. You can also take advantage of the numerous nearby adventure treks, such as Mount Hood, Multnomah Falls, and Larch Mountain.


As the largest city in Central Oregon, Bend is a great place to explore all the area offers. It's lively downtown features many unique and locally-owned boutiques, galleries, restaurants, and breweries.

Here you can participate in various outdoor activities, such as skiing and snowshoeing at nearby Mount Bachelor or hiking and camping at Smith Rock State Park. In addition to its outdoor activities, Bend is also home to some of the best organic wineries in the area.

Visit Volcano Vineyards for a memorable tasting experience with stunning views of the Cascade Mountains. You can also take advantage of adventure treks like rafting on the Deschutes River or visiting the High Desert Museum.


Boasting a vibrant downtown, Ashland is one of the best small towns in Oregon for historic charm. This charming community has many unique shops, galleries, and some of the state’s most beloved restaurants.

Don’t forget to explore the nearby organic wineries and microbreweries when you're in town. And if you’re feeling adventurous, take advantage of the many adventure treks just a short drive away.

From Mount Ashland to Crater Lake National Park, there’s something for everyone in this picturesque small town.

Oregon has something for everyone, no matter which town you explore. Its best small towns provide the perfect backdrop for a memorable getaway full of organic wineries, adventure treks, and historic charm. So pack your bags and start exploring!

Historic Charm

Oregon is home to some of the oldest and most historically significant ghost towns in the United States. Oregon’s ghost towns provide a unique glimpse into its colorful past, from former gold rush towns to old logging camps.

One of the best small towns for exploring these historic sites is Jacksonville. This quaint town was once one of Oregon’s largest gold rush towns, and today it still holds some of the most impressive historic attractions.

Stroll through its downtown streets to experience its unique charm, or visit the Jacksonville Museum to learn more about the town's history. You can also take advantage of adventure treks nearby, like Applegate Lake or Upper and Lower Table Rocks.

If you’re up for an even more unique experience, explore Oregon’s oldest ghost town, Shaniko. This small town was once a bustling trading post in the 1880s, and today it provides a fascinating glimpse into the past.

Visit Shaniko to explore its old general store, churches, saloons, and hotels. You can also take advantage of adventure treks nearby, like the Shaniko Badlands and the National Historic Oregon Trail Interpretive Center.

Organic Wineries

Oregon’s small villages are home to some of the best organic wineries in the country. From Willamette Valley to Yamhill County, numerous wineries offer tastings and tours for visitors. If you want a unique experience, visit Carlton in Yamhill County.

This charming village is home to some of the state’s best organic wineries, like Elk Cove Vineyards and Stag Hollow Winery. Explore their vineyards and sample their award-winning wines while you take in picturesque valley views.

You can also take advantage of nearby adventure treks, such as hiking through Ewing Young State Park or biking along the Willamette Valley Scenic Bikeway.

For an even more unique experience, visit the small village of Dundee in Oregon’s wine country. You can explore some of the area's best organic wineries, such as Lange Estate Winery and Hawks View Cellars.

Adventure Treks

Oregon is renowned for its outdoor activities, abundant hiking trails, kayaking spots, and rock climbing areas. To uncover some of the best adventure treks in the state, visit Hood River.

This small town on the banks of the Columbia River offers a wide array of outdoor activities. Go kay along the majestic river, or explore the many hiking trails. If daring, try rock climbing at Tooth Rock or Tamanawas Falls.

For a unique experience, take the Historic Columbia River Highway and explore the stunning waterfalls that line this historic highway. And when you’re done exploring, visit the vibrant downtown area of Hood River to experience its small-town charm.

From historic ghost towns to organic wineries and adventure treks, Oregon’s best small towns are full of surprises. So pack your bags and start exploring this beautiful state. You’ll be sure to find something that fits your taste!


What are the best small towns in Oregon for historic charm?

Oregon has many small towns with abundant history, charm, and quaintness. Some of the best small towns to explore for historic charm are Jacksonville, Oregon City, Brownsville, Astoria, and The Dalles.

Each of these towns offers something unique in terms of its architecture, museums, galleries, and parks - making them great places to explore and get a taste of Oregon's rich cultural history.

Are there any organic wineries in the state?

Yes, there are several organic wineries in the state of Oregon. These include Lemelson Vineyards, Left Coast Cellars, Carlton Cellars Winery, and Apolloni Vineyards.

Are there any adventure treks I can take in Oregon?

Yes, Oregon offers many opportunities for adventure and exploration. Popular activities include rafting on the Deschutes River, hiking in the Cascade Mountains, camping at Crater Lake National Park, and biking in the coastal range.


If you're looking for a place to get away from it all and experience the best Oregon offers, these towns should be at the top of your list. Whether it's a historic charm, organic wineries, or outdoor adventure that you want, these small towns in Oregon can provide it.

From the sprawling vineyards of Willamette Valley to the cool mountain passes near Bend, there's something for everyone here.

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