The historic Liberty Theater and downtown Astoria. Image credit Bob Pool via Shutterstock.

7 Oldest Founded Towns To Visit In Oregon

Oregon is a beautiful state located in the Pacific Northwest region of the United States. It is the tenth-largest state in terms of area and has a population of almost 4.2 million people. The state is renowned for its stunning natural beauty, offering visitors the unspoiled wilderness of old-growth forests, abundant wildlife, and picturesque views of the Pacific Ocean.

While the natural beauty is a prime attraction, Oregon's small towns also have rich historical legacies. Often, these places were founded as trading posts, railroad towns, or havens for early settlers traveling the Oregon Trail. They offer valuable lessons, telling the stories of early American pioneers who often battled harsh conditions as they built their lives in a brave, untamed world. The following towns are some of the oldest-founded towns to visit in Oregon, offering glimpses into the past. Still, if we are wise, they can offer a roadmap to facing the future with unwavering hope and unmoveable determination.


Liberty Theater is a historic vaudeville theater and cinema in Astoria, Oregon
Liberty Theater is a historic vaudeville theater and cinema in Astoria, Oregon, via Sveta Imnadze /

Astoria sits at the mouth of the Columbia River as it empties into the Pacific Ocean. It enjoys a rich maritime history as the oldest settlement in the state, having been founded in 1811 as an early fur trading port. The town is named after John Jacob Astor, whose company, the American Fur Company, used the bay's deep waters to ship furs and pelts back east. Visitors will appreciate the city's enduring charm, with the Columbia River Maritime Museum featuring some of the finest displays of shipwrecks and artifacts in the Northwest. The Fort Clatsop National Memorial, which housed Lewis and Clark on their expedition through the area in 1805, is nearby. The Flavel House is a beautiful example of Victorian architecture owned by one of the town's first residents. Be sure to explore the Astoria Column, a 125-foot column with sgraffito murals depicting various events in Oregon's history, located on Coxcomb Hill. Its observation deck is accessible by climbing a spiral staircase, offering magnificent views.

The downtown district boasts a variety of shops, galleries, and restaurants, including notable places like the Silver Salmon Grille or Bridgewater Bistro for fresh seafood.

For outdoor adventurers, numerous trails for hiking surround the community, from the Young River Falls, about 15 minutes outside Astoria, to the trails in Fort Stevens State Park in nearby Hammond. Keep an eye out for the diverse wildlife in the region, including mule deer, beavers, and raccoons.

Oregon City

Landmark historical house in Oregon city
Landmark historical house in Oregon city

Oregon City, located about thirty minutes south of Portland in Clackamas County, has a profound historical legacy as one of the earliest settlements in the Oregon Territory, founded in 1829. Its strategic location near Willamette Falls and the abundance of timber made it a hub for lumber harvesting. Many settlers arrived here after traversing the challenging Oregon Trail, a fact celebrated by the Museum of the Oregon Territory, which also offers scenic views of the falls. The End of the Oregon Trail Interpretive Center showcases the stories of these pioneers.

Outdoor enthusiasts will enjoy the Hopkins Demonstration Forest Outer Loop, a 2.8-mile hike through a 140-acre forest. The Newell Creek Canyon Trail, a 3.2-mile loop through meadows and dense forests, is popular among joggers and bikers, though pets are not allowed.

The downtown area offers an eclectic mix of boutiques, art galleries, and restaurants. The Farmer's Market features fresh produce from the Willamette Valley, and Tony's Fish Market has been a community staple since 1936. For dining, the Stone Cliff Inn provides a rustic mountain experience.


Buildings in the downtown historic district in Jacksonville.
Buildings in the downtown historic district in Jacksonville. Image credit Underawesternsky via Shutterstock.

Jacksonville, a former Gold Rush town, is now a vibrant arts community. Named after Jackson Creek, the site of one of the area's first gold claims in 1851, Jacksonville is a National Historic Landmark with well-preserved Gold Rush-era buildings. The Britt Music Festival draws visitors every summer for concerts, and the nearby Rogue Valley is renowned for its wineries. History enthusiasts can explore local history through various museums and historical sites.

The Rogue Valley's reputation for fine wineries, such as those specializing in pinot noir and chardonnay, adds to the area's appeal. The city's wine trolley offers a unique way to explore these local vintners.

Several restaurants in the historic downtown area, like The Restaurant at the Jacksonville Inn or C-Street Bistro, offer farm-to-table dining experiences. For accommodations, the McCully House Inn and the Touvelle House are notable bed-and-breakfasts, ideal for a weekend getaway.

Port Orford

Cape Blanco Lighthouse at Cape Blanco State Park near Port Orford on the Oregon coast.
Cape Blanco Lighthouse at Cape Blanco State Park near Port Orford on the Oregon coast.

Port Orford, the oldest settlement on the Oregon Coast, is renowned not only for its natural beauty but also for its historical significance. First visited by European explorers in the late 1790s, the area was established as a fort in 1851. While it offers outdoor activities, it is more widely known for its fishing industry. The Port Orford Lifeboat Station Museum provides insights into the early Coast Guard's history in the region. The Curry County Historical Museum, located in nearby Gold Beach, is also worth exploring.

State parks such as Port Orford Heads State Park offer trails along the rocky coastline with stunning ocean views. Battle Rock Park and Garrison Lake within the town provide excellent opportunities for ocean viewing, boating, and fishing. For those interested in whale watching or lighthouses, Paradise Point State Park and Cape Blanco Lighthouse, 17 miles north in Cape Blanco State Park, are must-visit destinations.

The town's Main Street is a designated Art District, showcasing local artists’ work in galleries like the Hawthorne Gallery. Dining options include Redfish, located in Battle Rock Park, known for its food and views.


Downtown Ashland in Oregon
Downtown Ashland in Oregon, via Brycia James /

Ashland, located in southern Oregon near the California border, is nestled in the Rogue Valley with the Siskiyou Mountains as its backdrop. Originally named after the Ashland Estate in Kentucky, the town's early economy was supported by sawmills and flour mills in the 1850s. The fertile soil, abundant resources, and mild climate made it attractive to settlers, especially after the Donation Land Claim Act of 1850.

Today, Ashland is famous for its Oregon Shakespeare Festival, offering a range of theatrical productions from mid-March through September. The festival, which started in 1935, has become a significant cultural event.

The town is also a hub for artists, with the Ashland Galleries Association featuring over 30 galleries and studios. The Art and Soul Gallery in the downtown district is a highlight. For dining, Alchemy Restaurant and Bar offers an immersive experience, and the Oak Hill Bed and Breakfast is a popular choice for accommodation.


Street view in Silverton, Oregon.
Street view in Silverton, Oregon. Image credit Laurens Hoddenbagh via

Silverton, near the capital city of Salem, Oregon, has a rich history dating back to the early 1840s. The original site, named Milford, was upstream on Silver Creek. Silverton's growth was driven more by agriculture and timber than the gold rush. The nearby Silver Falls State Park is known as the "Crown Jewel" of the state, famous for its Trail of Ten Falls, which meanders through old-growth forests past stunning waterfalls. The park also offers 35 miles of trails for various outdoor activities.

The Oregon Garden, an 80-acre botanical haven, is ideal for a romantic stroll, complemented by the Garden View Restaurant. Silverton's downtown area features a vibrant mix of boutiques, galleries, and restaurants. The town is a supporter of the arts and history, with attractions like the Silverton Country Historical Society Museum and the Gordon House, Oregon's only Frank Lloyd Wright-designed building.

The Dalles

View along 2nd Street in The Dalles Oregon with the Granada Theatre
View along 2nd Street in The Dalles Oregon with the Granada Theatre, via Ian Dewar Photography /

The Dalles, located in the Columbia River Gorge National Scenic Area, has a rich history that dates back nearly 10,000 years, serving as a trading post for Native American tribes. Lewis and Clark's exploration of the Columbia River in 1805 included a camp near The Dalles, which later became an essential stop on the Oregon Trail. The Columbia Gorge Discovery Center offers insights into the region's long history.

West of The Dalles, the Columbia River Gorge National Scenic Area offers numerous recreational opportunities. The Dalles Riverfront Trail is ideal for family biking, while the Lyle Cherry Orchard Trail provides a scenic wildflower walk. The town's Main Street features a variety of shops and points of interest, including the National Neon Sign Museum. Cousins Restaurant is a local favorite, known for its hearty meals.

In Conclusion

A visit to any of Oregon's small towns, like Silverton or The Dalles, offers a blend of scenic beauty and historical depth. These towns, often established as commercial centers for pioneers on the Oregon Trail, showcase the resilience and perseverance of those who built lives in the wilderness.

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