Nature-filled adventures await in the wild and carefree lands of Oregon. Beyond the beautiful sights found in Portland, Oregon’s most underrated towns have a plethora of hidden and unique attractions that have remained practically unchanged since the arrival of Lewis and Clark. Whether you are enjoying the coastal playgrounds of Florence and Cannon Beach, reliving the route of the Oregon Trail in The Dalles or Baker City, or undertaking your own adventures in the wilderness in Hood River and Yachats, the Beaver State has enough amenities to sink your buckteeth into. Come appreciate Oregon’s most underrated towns in 2024.
Florence
Recognized by many who visited to be “Oregon’s Coastal Playground,” the small town of Florence is a spectacular getaway location at the mouth of the Siuslaw River. Given the right time of year, visitors can be treated to the sight of Steller sea lions migrating at the expansive Sea Lion Caves. Elsewhere, hiking and biking trails circling the restored 19th-century Heceta Head Lighthouse provide unparalleled views of frolicking seabirds and roving whales across the Pacific Ocean.
March 23rd to the 31st is a particularly prime period to do some whale watching in Florence. Across the Siuslaw River, rolling sand dunes of the Oregon Dunes National Recreation Area allow travelers to participate in exciting dune buggy rides or even horseback riding. If you want to spend your long days or weeks in the prosperous town of Florence, then find accommodations at the Old Town Inn, River House Inn, or Driftwood Shores Resort.
Coos Bay
As the largest deep-draft port between Puget Sound and San Francisco, the town of Coos Bay has embraced many travelers from land and sea. About an hour away from Florence, Coos Bay has a similar array of towering sand dunes that one can jubilantly explore. In the area, you’ll find the Elliott State Forest and the Shore Acres State Park, which promote numerous wildlife and habitats in the Oregon region. The Cape Arago Highway leads to magnificent and unspoiled coastal sceneries.
In the town itself, the Coos Art Museum exhibits many avant-garde pieces for your aesthetic viewing, while the Coos History Museum unfolds the compelling past. One ought not to miss the Oregon Coast Music Festival in July. If you want to stay a while, the Itty Bitty Inn or Edgewater Inn Coos Bay will certainly be wonderful accommodations.
Hood River
Carefree winds stir people to windsurfing adventures in the town of Hood River. With Hood River’s prime location near Mount Hood and the Columbia River Gorge, thrill-seekers can enjoy windsurfing escapades throughout the area. On Mount Hood, the Timberline Trail circumnavigates the whole mountain, while the Cooper Spur Trail reaches the highest reachable hiking point. Either path is dotted with windsurfing stations to give you a head-start in the air. Meanwhile, in the Columbia River Gorge, there are many waterfalls and camping sites to relax your weary soul. When all of nature’s splendors have delighted you, give yourself a much-needed break at the Hampton Inn & Suites Hood River or Columbia Gorge Hotel and Spa.
Baker City
Since its establishment in 1874, Baker City has been a vital epicenter for trade and rest between Salk Lake City and Portland. The town built its roots on the Oregon Trail, hence why it has been referred to as “eastern Oregon’s base camp.” The Baker Heritage Museum or the Eastern Oregon Museum illustrates more on Baker City’s trailblazing heritage. Or you can brave the nearby Wallowa Mountains and the Elkhorn Mountains, part of the Blue Mountains. In the Farewell Bend State Park, visitors are entreated to the remains of old wagon wheel ruts from the pioneering age. You can also find good lodgings at the historic Geiser Grand Hotel to better appreciate the pioneering past.
Cannon Beach
Cannon Beach, only 90 minutes from Portland, has seen thousands upon thousands of visitors traipse on its sandy shores. So named after a naval cannon found on the shore—the only remains of a shipwreck long ago—people come to this mesmerizing town for crystal-perfect sand and seas, but most of all for the iconic 235-foot-tall Haystack Rock, a natural monument to Cannon Beach’s magical atmosphere.
The surrounding terrain is also rife with mystical attractions. In Ecola State Park, trails showcasing the majesty of the land and sea will dazzle explorers. Nearby, Arcadia Beach contains picnic areas to luxuriate by the seaside, as well as tide pools to wade around. Should you wish to stay a while, The Wayside Inn, Beachcomber Vacation Home, Argonauta Inn, or AvantStay have many services suitable for your leisure.
Jacksonville
The Jacksonville of Oregon is remarkably different from the Jacksonville in Florida. There is a lot of vibrant scenery in a town conveniently located five miles from Medford. In addition, Jacksonville, Oregon, is a National Historic Landmark due to the 1850s gold deposits that allowed the town to prosper. It also happens to be situated at the foot of the Siskiyou Mountains, a pristine destination for hiking and trekking. Moreover, Jacksonville hosts the Britt Music & Arts Festival, a celebration of all things musical, to be announced in April this year. As evidence shows, the town of Jacksonville is a humble and soothing settlement for people who want to retreat from the big cities. When it comes to accommodations, the Wine Country Inn, Kubli Haus, Magnolia Hotel, and The Jacksonville Inn are among the best you can find.
Joseph
The town of Joseph has been hailed as the “Little Switzerland of America” because of its scenic spot on the Wallowa Mountains and its overlook location near the Hells Canyon. Joseph derived its name from Chief Joseph of the Nez Perce tribe, and the town honors the chieftain by hosting an annual Tamkaliks celebration. Wallowa County Museum provides more insight into Joseph’s past, while the Wallowa County Farmers’ Market offers the many ripe and juicy bounties of Oregon. Take a trip to Wallowa Lake to catch some trophy-sized fish, or brave the Eagle Cap Wilderness to relish in the wild side of Joseph. When it comes to lodgings, the Bronze Antler Bed & Breakfast, Eagle Cap Chalets, Flying Arrow Resort, and Trouthaven Resort are a few excellent examples of where you ought to spend your evenings.
Yachats
Water rushes into Thor’s Well on the Pacific Ocean as the sun sets over Oregon.
The small town of Yachats (pronounced yah-haats) derives its name from the Siletz language, meaning “dark water at the foot of the mountain.” Indeed, many of the waters clashing at the shoreline are dark with ferocious rock formations, especially at the Yachats Ocean Road State Natural Site. If one wishes to gain the high ground, then the Ya’Xaik (yah’ khik) Trail and Amanda’s Trail can lead you to Cape Perpetua, the highest vantage point accessible by car on the Oregon Coast. But the greatest and most mesmerizing natural attraction in Yachats is Thor’s Well, a natural drainage hole where the waters of the Pacific cascade down into an unknown abyss. Find opulent lodgings at the Overleaf Lodge & Spa, Ocean Cove Inn, or the Yatel Motel.
Ashland
For lovers of Shakespearean drama, the town of Ashland hosts the time-honored Oregon Shakespeare Festival from March through May of 2024. Situated in the Rogue River Valley at the base of Siskiyou Mountain, anyone—from actors to audience—can participate in the Bard’s many transcendental plays. Aside from theater, Ashland is a patron of other arts, as best seen in the Ashland Artworks Gallery and the Schneider Museum of Art. Even the surrounding landscape has many masterpieces to showcase, such as Lithia Park or Mount Ashland. Do not forget to book rooms at the Swank & House, The Winchester Inn, Stay Ashland, or The Bard’s Inn Hotel.
Silverton
Silverton is affectionately called “Oregon’s Garden City” because of the perennial enchantments found in the Oregon Garden. About 41 miles from Portland, travelers can feel like they are in a wonderland in Silverton’s Oregon Garden, an over 80-acre park composed of sublime horticultural plots and lands. One can find several specialty plots like a Children’s Garden and a Pet-Friendly Garden. There are even a few cultural and yearly events in these botanical fields, such as the Arts in the Garden. Aside from the local flora, the Silver Falls State Park is home to the brilliantly cascading “Trail of Ten Falls.” No need to be worried about accommodations because the Oregon Garden Resort, the Silverton Inn and Suites, and Edward Adams House B&B are a few places where you can feel relaxed as you enjoy the floral atmosphere of Silverton.
Sisters
The town of Sisters shares its familial name with the three volcanic peaks looming protectively over the area. As a town surrounded by the Cascade Mountains and Oregon’s high-desert region, Sisters is a gateway to several notable preserves and vantage points. The Three Sisters Wilderness, for example, is a landmark of stunning vistas from an alpine altitude. The nearby Deschutes National Forest is carpeted by familiar ponderosa pine trees, while the Smith Rock State Park contains over 650 acres of arid deserts for those who wish to brave the hotter side of Oregon. The Pacific Crest Trail creates many opportunities for uninterrupted exploration, and on June 5th through the 9th in 2024, there will be a Sisters Rodeo, “The Biggest Little Show in the World,” that promises entertainment and action. Once all the excitement gets you weary, stay a while at the Best Western Ponderosa Lodge, the Black Butte Ranch Vacation Rentals, or the Long Hollow Ranch.
The Dalles
For 10,000 years, The Dalles has been a trading center for Native Americans, marking it as one of the oldest permanently occupied settlements in Oregon. Only 20 miles east of Hood River, many explorers of the past and the present have charted this vibrant region of the Columbia River Gorge. In the town itself, the Columbia Gorge Discovery Center and Museum provides illuminating exhibits that elucidate the Lewis and Clark Expedition in 1804. The Fort Dalles historic site contains a replica of an 1850s US Army Outpost that memorializes The Dalles’ pioneer history. This town is also where the old Oregon Trail ended, which may inspire you to rest up like Lewis and Clark at the Cousins Country Inn, Comfort Inn Columbia Gorge, or Celilo Inn.
Astoria
There is a certain itch of nostalgia whenever you are exploring Astoria, the “little San Francisco.” That is because the classic movie, The Goonies, was filmed in the quaint seaside town. As a pleasant, movie-worthy location that borders both the Pacific Ocean and the Columbia River in northwest Oregon, travelers may enjoy a leisurely stroll along Astoria Riverwalk. The Columbia River Maritime Museum and the Astoria Riverfront Trolley explain Astoria’s intriguing history while also having impeccable seafood restaurants for your tastebuds. Lastly, the Buoy Beer Company and Fort George Brewery are a few locations that are great for catching up with friends over a drink. As for lodgings, the Astoria Riverwalk Inn and the Selina Commodore Astoria are pristine hostels on the West Coast.
Often, the roads less traveled lead to more thrilling destinations than well-paved paths and trails. In Oregon, there are many of these trails that lead to the most underrated small towns in the Beaver State. And each of these small towns has unique cultural, historical, and natural treasures that you will just love. From dynamic landscapes like Sisters and Coos Bay to drama-enthusiastic abodes like Ashland, there are surprises aplenty in the fiercely gorgeous wilderness of Oregon. So undertake your own trail in Oregon and feel the breeze of the Pacific Ocean caress the forests and fields of the West Coast.