The Historic District of Cottage Grove, Oregon.

These Small Towns In Oregon Have The Best Historic Districts

Situated in the beautiful Pacific NorthwestOregon is renowned for its stunning natural beauty, lively cities, charming beach communities, and welcoming small towns. With a Euro-American history going back to the Lewis and Clark Expedition and a Native American history stretching back centuries further, the “Beaver State” is full of great places to explore the past. Many of Oregon’s fun, safe, and tourist-friendly small towns have excellent historic districts perfect for a walking tour. Check out these seven great historical towns to help you explore the northwestern gem of Oregon.

Sisters

A view looking down the Main Street in downtown Sisters, Oregon.
A view looking down the Main Street in downtown Sisters, Oregon. Editorial credit: Bob Pool / Shutterstock.com

While rugged coastal towns might come to mind when you think of Oregon, the community of Sisters in the central part of the state looks and feels like an Old West town. Named for the Three Sisters Mountains, Sisters has tripled in population since 2000 but still has only about 3,000 residents, many of whom have come specifically to enjoy the cowboy town environment. Downtown Sisters feels like a classic Western film set brought to life, including historic structures like the 1912 Hotel Sisters building. While on your walking tour, explore the town’s many cowboy-themed businesses selling clothing, art, antiques, and more. Visit in June to experience the annual Sisters Rodeo.

McMinnville

Military fighter aircraft Grumman F-14 Tomcat on exhibition at Evergreen Aviation & Space Museum.
Military fighter aircraft Grumman F-14 Tomcat on exhibition at Evergreen Aviation and Space Museum. Editorial credit: Png Studio Photography / Shutterstock.com

McMinnville sits along the Yamhill River in northwest Oregon’s lovely Willamette Valley, which is also the heart of the state’s wine country. Pinot Noir is the McMinnville area’s specialty, but several wine varieties are produced in the region. After taking a wine tour of the area, head to McMinnville’s downtown shopping district, where numerous historic buildings house a range of boutiques and eateries. Then, to experience aviation history, visit the Evergreen Aviation and Space Museum. The museum’s star attraction is the World War Two era Spruce Goose, the brainchild of the eccentric multimillionaire Howard Hughes and the largest wooden airplane ever built. Visit McMinnville in September to check out the Oregon International Air Show.

Florence

Aerial view of Heceta Head Lighthouse near Florence, Oregon.
Aerial view of Heceta Head Lighthouse near Florence, Oregon.

It is rather unfortunate that Florence’s biggest claim to fame may be the ill-fated 1970 attempt to blow up a beached whale carcass with dynamite, although the locals take it in good spirits, including by dedicating an “Exploding Whale Memorial Park” in 2020. In reality, Florence deserves to be best known as one of the loveliest communities along Oregon’s picturesque coastline. The town sits at the mouth of the Siuslaw River, and the Art Deco-style Siuslaw River Bridge (1936) is one of the architectural highlights of the Old Town neighborhood along the waterfront. The nearby Siuslaw Pioneer Museum recounts the region’s history, while the Heceta Head Lighthouse offers unsurpassed views of both land and sea.

Cottage Grove

Currin Covered Bridge near Cottage Grove, Oregon.
Currin Covered Bridge near Cottage Grove, Oregon.

If you love the historic charm of classic wooden-covered bridges, the Willamette Valley community of Cottage Grove is a must-visit. Nicknamed “The Covered Bridge Capital of the West,” the town of 10,000 residents and its immediate vicinity are home to six covered bridges, most of which date from 1930 and earlier. The scenic downtown area houses four history museums and has been a setting for several films, including Animal House (1978) and Buster Keaton’s The General (1926). Also, starting right in the heart of Cottage Grove’s Historic Downtown District, the Row River National Recreation Trail is an old rail bed that traces 14 miles along the beautiful Row River and Dorena Reservoir.

Cannon Beach

Haystack Rock in Cannon Beach, Oregon.
Haystack Rock in Cannon Beach, Oregon.

Cannon Beach is best known for Haystack Rock, a majestic monolith that rises some 235 feet above the ocean surf. While this natural wonder is definitely worth seeing up close, also check out the elevated view from Ecola State Park, where famed explorer William Clark first gazed on Haystack Rock back in 1805. In addition to Haystack Rock and the sandy beach that surrounds it, the town of Cannon Beach itself has plenty of history and charm to draw in visitors. Home to a thriving artistic community, the town houses a lovely mix of galleries, shops, and eateries. Take a stroll through the Presidential Streets District to glimpse classic little beach cottages nestled alongside both historic and modern beach mansions.

Baker City

Main Street in the historic district of Baker City, Oregon
Main Street in the historic district of Baker City, Oregon. 

A town of about 10,000 residents set along the Powder River and surrounded by the Wallowa Mountains and the Elkhorn Mountains in eastern Oregon, Baker City draws in two main categories of visitors. The first category includes hikers, anglers, kayakers, hunters, and other outdoor enthusiasts who make use of Baker City’s spectacular natural setting. The second category is made up of history lovers, in part because the Baker City Historic District is home to one of the best collections of nineteenth-century architecture in Oregon. History buffs also flock to the Baker Heritage Museum, which includes materials on early town history, the Oregon Trail, gold mining, Chinese immigration during the railroad boom, and more.

Astoria

Aerial view of Astoria, Oregon.
Aerial view of Astoria, Oregon.

Established in 1811 at the strategic meeting point of the Columbia River and the Pacific Ocean, Astoria spent its first century or so as a critical port for the fur, lumber, and fishing industries. The Port of Astoria remains active today, but tourism is now the town’s main industry, thanks to Astoria’s picturesque location and wealth of historic buildings. While downtown Astoria is perfect for a walking tour, ramp up the charm factor by taking in the sights on the town’s vintage trolley. From the replica of tiny Fort Astoria (1811) to the towering John Jacob Astor Hotel (1924), Astoria showcases its historic place as the oldest American town west of the Rocky Mountains.

If you are looking to explore historic small towns that also have friendly locals and fine weather, Oregon should be near the top of your travel list. Whether your historical interest tends toward the Old West, Victorian architecture, or Native American culture, Oregon has communities that will exceed your expectations. Use our list of historic small towns as a starting point, then do some exploring on your own—you are guaranteed to uncover additional small-town gems in the Beaver State!

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