10 Most Beautiful Small Towns in Oregon

Oregon is one of the most diverse states in the United States and full of diverse ecosystems. Framed by snowy mountains, Pacific coastline, and rolling green hills, the small towns in Oregon are just as picturesque. Every small town has a unique feel and culture, making a town-hopping day trip or two an excellent choice. Here are the 10 most beautiful small towns in Oregon.

1: Ashland

Ashland
Photo Courtesy: Flickr/IIP Photo Archive

Known outside of Oregon for award-winning Shakespeare performances at the Oregon Shakespeare Festival, you will find Ashland to be an artistic, elegant town of only 21,000 residents. Located in the beautiful Rogue Valley, Ashland is home to the Southern Oregon University and features various hiking trails, beautiful ponds, majestic mountains, and rushing rivers. For those who love greenery, the campus has a fair share to see, but you also don’t want to overlook the 100-acre Lithia Park set right in the middle of the town. There is also the Blue Giraffe Spa or Grizzly Peak Winery for those who want to be pampered.

Address: Ashland, OR

2: Astoria

Astoria
Photo Courtesy: Flickr/ktkochan

Quaint is the word that comes to mind when talking of this town. Being the oldest settlement west of the Rockies, Astoria has a Victorian-era-meeting-maritime feel that can only be found here. Historic forts dot the area, as do a number of museums and local beer breweries. Foodies, adventurists, and artists will also love the fresh seafood, eclectic spread of shopping opportunities, and a number of museums, including the Lewis and Clark National Historic Park. Many events are also held in Astoria throughout the year, including the Annual Goonies Day in June.

Address: Astoria, OR

3: Hood River

Hood River
Photo Courtesy: Flickr/m01229

Located in the heart of Columbia River Gorge, the vibrant town of Hood River offers magnificent views of nature scenery, breathtaking mountains, waterfalls, and scenic trails. The town has a moderate climate and receives less rain than any other places in Oregon. You can climb Mt. Hood, sip some wine at Marchesi Vineyards or Naked Winery, and then take a tour at Full Sail Brewing Company for beer. Outdoor activities include hiking, white-water rafting, and cycling.

Address: Hood River, OR

4: Brownsville

Brownsville
Photo Courtesy: Flickr/Doug Kerr

Formerly known as Calapooya after the Kalapuya Native Americans who once settled in this region, Brownsville is a small town in Linn County along the Calapooia River. Though the town’s original claim to fame was having the first original county courthouse, it is now known for being the main shooting location for the film 'Stand By Me'. Many of the buildings remain from the late 1800s and early 1900s, and a must see is the Moyer House, an Italian villa. Apart from the historic downtown, there is also the lovely 26-acre Pioneer Park to see.

Address: Brownsville, OR

5: Cottage Grove

Cottage Grove

Hop off of Interstate 5 in Lane County and you will find yourself a gem. Cottage Grove, like many places in Oregon, has a history connected to pioneering during the 1800s. There are railroads and covered bridges abound here, making it the “Covered Bridge Capital” of Oregon. Be sure to schedule your visit around the Bohemia Mining Day festival; or if you miss it, check out the Bohemia Gold Mining Museum instead.

Address: Cottage Grove, OR

6: Florence

Florence
Photo Courtesy: Flickr/Kirt Edblom

Charming Florence has abundant coastline scenery as well as swaths of forest to explore. Visitors who are seeking some thrills can rent a dune buggy and zip along the sand dunes throughout the Oregon Dunes National Recreation Area or explore the Sea Lion Caves—home to Steller Sea Lions year round. Those seeking a nice hike should check out Heceta Head Lighthouse or the vibrancy of Historic Old Town, set along the Siuslaw River. Don’t forget to walk the stunning Siuslaw River Bridge.

Address: Florence, OR

7: Baker City

Baker City

Located on the Historic Oregon Trail, Baker City thrives on the history that made it. Within the Historic District, you will not only look into the ages, but you will find a lot of current trends too. There is also the Baker Heritage Museum (Fall Colors Tour is a must) and National Historic Oregon Trail Interpretive Center that will make history buffs and old-school gamers delighted. Afterwards, hop aboard the Sumpter Valley Railway or go quench your thirst at the Baker City Brewing Company or one of the many pubs.

Address: Baker City, OR

8: Jacksonville

Jacksonville
Photo Courtesy: Flickr/Harold Litwiler

Have a thing for a traditional American setting? Jacksonville has a charm about it that may remind you of a historic street in NYC. With a history linked to the Gold Rush and Oregon’s first Chinatown, this tiny town is full of character. There are also six tasting rooms for wine and liquor, boutique fashion shops, and other treats to be found. In the summertime, there is an outdoor concert series known as Britt Fest, which features the Britt Orchestra, Diana Krall, and Michael Franti & Spearhead, to name a few.

Address: Jacksonville, OR

9: Joseph

Joseph
Photo Courtesy: Flickr/Forest Service

Outdoor enthusiasts will find nirvana in Joseph—the Little Switzerland of America. You can travel through the Wallowa Mountains and Eagle Cap Wilderness nearby. Shoppers will enjoy Main Street, which is lined with art galleries, restaurants, cafes, and boutique shops. Be sure to bring your camera to take pictures of the famous bronze sculptures along the road, too. And if you are looking for a real Oktoberfest in the States, complete with yodeling and alphorn, check out the annual Swiss-Bavarian festival.

Address: Joseph, OR

10: Sisters

Sisters
Photo Courtesy: Flickr/Bonnie Moreland

This small Oregon town was named for the three mountain peaks known as the Sisters that tower over the buildings and streets. Visiting Sisters is like hopping into a Delorean and taking a trip back to the 1880’s Wild West. The buildings have western facades, and the place is full of artwork. Surrounding the small town are a number of camping, skiing, and fishing opportunities; but if you want to really relax, you are going to want to visit America’s first beer spa at Deschutes Brewery where hot tubs of hoppy goodness await.

Address: Sisters, OR

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