10 Whimsical Towns to Visit in Oregon
All journeys have an end, but for you, the adventures can start in the Beaver State of Oregon. Where the dynamic duo, Meriwether Lewis and William Clark, ended their nation-spanning journey, Oregon contains a number of whimsical small towns sprouting in the evergreen and ever-growing forests and mountains. Whether you are admiring the Pacific Ocean from Cannon Beach and Yachats or feeling the full rush of adrenaline in adventurous towns like Hood River and The Dalles, you will be blessed as many have undertaken the Oregon Trail with spectacular experiences in Oregon. So, whatever vehicle you are traveling or however you wish to sojourn, let the whimsical towns of Oregon sweep you off your feet.
Hood River
Hood River is a town in the Columbia River Gorge that campaigns for adventure. The Timberline Trail and the Cooper Spur Trail are two routes for you to take to ascend Mount Hood’s highest possible point. From the slopes of Mount Hood, travelers can undertake windsurfing, an aerial pastime for those wanting the freedom and leisure of the wind. Meanwhile, at the Columbia River Gorge, you can journey towards the many beautiful waterfalls and pitch a tent in several ideal camping grounds if you prefer the outdoors than idling indoors. Naturally, a town like Hood River still provides a number of lodgings for you to stay at, such as the Hampton Inn & Suites Hood River or Columbia Gorge Hotel and Spa. So do not feel anxious or fatigued when you are having a blast in the windy world of Hood River.
Ashland
Ashland is one of the best places to get to know William Shakespeare’s ingenuity despite being so far away from Britain. The much-admired Oregon Shakespeare Festival, beginning from February and ending at November, treats visitors and locals to the many tragedies and comedies made by Shakespeare. Outside of the Bard’s influence in Oregon, Ashland contains some of the finest fine arts pieces in the state as best seen in the Ashland Artworks Gallery and the Schneider Museum of Art. Those with more active appetites ought to go exploring in Lithia Park, Mount Ashland, the Rogue River Valley, and at the slopes of the Siskiyou Mountain. So consider spending your lively and theater-loving days and nights at either the Swank & House, The Winchester Inn, StayAshland, or The Bard’s Inn Hotel.
Cannon Beach
Only around 90 minutes from the city of Portland, Cannon Beach has been one of the trendiest and most visited destinations in Oregon. Renowned for its pristine sand and its iconic attractions—for instance, the 235-foot-tall monolith called Haystack Rock—Cannon Beach has captivated thousands of visitors each year. The location was named after the remains of a naval cannon discovered on the beach, and many flock to shorelines like the Ecola State Park and Arcadia Beach to uncover more seaside surprises or to create memorable experiences beside the Pacific Ocean. In Arcadia Beach specifically, you can enjoy the twirling delights of tide pools. You need not be concerned about accommodations, because establishments like The Wayside Inn, Beachcomber Vacation Home, Argonauta Inn, and AvantStay will have all you need and more.
Joseph
Joseph, the “Little Switzerland of America,” can be found on the slopes of the Wallowa Mountains. From such an impressive vantage point, one can gaze down at Hells Canyon or wade in the chill waters of Wallowa Lake. Joseph’s name originated from Chief Joseph of the Nez Perce tribe, and the yearly Tamkaliks celebration pays homage to Chief Joseph and the Nez Perce people. Learn more about Joseph’s history at the Wallowa County Museum, or you can purchase fresh and delicious bounties at the Wallowa County Farmers' Market. Afterwards, venture into the Eagle Cap Wilderness to see the many magnificent animals of Oregon’s wilds. Should the cool mountain air get too chilly, warm up at the Bronze Antler Bed & Breakfast, Eagle Cap Chalets, Flying Arrow Resort, or Trouthaven Resort.
Yachats
The town of Yachats (pronounced yah-hots) derives its name from the Siletz phrase “dark water at the foot of the mountain.” This is most likely an allusion to the dark rock formations seen at the Yachats Ocean Road Natural Site as well as Thor’s Well, a natural drainage hole siphoning the Pacific Ocean into a darkly unknown location. Aside from these darkly mysterious features of Yachats, the town is also abundant with serene and simplistic trails such as the Ya’Xiak (yah' khik) Trail and Amanda's Trail. These routes will take you all the way to Cape Perpetua, the highest point on the Oregon Coast. So if you are intrigued by the dark waters of Yachats or its mountainous landscape, then you ought to book a room at the Overleaf Lodge & Spa, Ocean Cove Inn, or the Yatel Motel.
Silverton
Silverton, “Oregon’s Garden City,” is a 45-mile getaway from Portland. Travelers will be delighted by the sight of the Oregon Garden, over 80 acres of floral pastures and fields lively with different flower species. The Oregon Garden is segmented into the Pet-Friendly Garden and Children's Garden, and there are a number of yearly events held in the garden such as the Arts in the Garden. Silverton is also renowned for its resplendent waterfalls as best explored in the “Trail of Ten Falls” at the Silver Falls State Park. There is no shortage of beautiful features to behold and experience in Silverton, and among them are the soothing establishments of the Oregon Garden Resort, the Silverton Inn and Suites, and Edward Adams House B&B.
Sisters
Within the trio of extinct volcanos in the Cascade Mountains lies the small town of Sisters. From the Three Sisters Wilderness abundant with Oregon’s high-desert wildlife, travelers can sojourn to the many spectacular desert destinations near Sisters. There are ponderosa pine trees to be found at the Deschutes National Forest. There are over 650 acres of desert biomes to be explored in the Smith Rock State Park. And there many more ferocious habitats and features to admire along the Pacific Crest Trail. Every year from June 5 - 9, Sisters hosts the Sisters Rodeo, “The Biggest Little Show in the World” which, as the title implies, showcases some of the smallest items and regalia you can find. Leave trepidation and anxiety out of the door as you spend your adventures in Sisters, and keep your belongings safe in secure lodgings like the Best Western Ponderosa Lodge, the Black Butte Ranch Vacation Rentals, or the Long Hollow Ranch.
The Dalles
The Dalles, about 20 miles east of Hood River, is one of the oldest settlements in Oregon, first being a trade nexus of the Native Americans for 10,000 years until pioneers established a more modern community in the 1800s. From the Columbia Gorge Discover Center and Museum, you can study up on the Lewis and Clark Expedition in 1805. From the Maryhill Museum of Art, you can admire the many interpretive and insightful artworks depicting the Columbia River Gorge which surrounds The Dalles. Immerse yourself deeper into the past at Fort Dalles, now a replication of US Army Outpost from the 1850s. Should you night grow colder and your body grow sleepier, then you can always recharge and refreshen at the Cousins Country Inn, Comfort Inn Columbia Gorge, or Celilo Inn.
Astoria
Although Astoria is often called the “little San Francisco” because of its miniaturized resemblance to the big city, it is nonetheless known by those who have watched the classic film, The Goonies. From the Astoria Riverwalk to the Columbia River Maritime Museum, there are several notable sights and sites beside the Columbia River that you might recognize from the film. There might also be locations you have not seen from The Goonies, such the Buoy Beer Company which offers promotional tours of its operations and wares. Then there is Fort George and the Astoria Riverfront Trolley, the latter promoting delicious seafood meals and restaurants for those with such an appetite. There are many such attractions in Astoria besides those seen in an old movie, and if you are invested in seeing more, you should definitely book a room at either the Astoria Riverwalk Inn or the Best Western Long Beach Inn.
Baker City
Located between the Elkhorn Mountains and Wallowa Mountains, which are part of the Blue Mountain Ranges, Baker City is a prosperous town often called “eastern Oregon’s basecamp.” With its position in the Oregon Trail, Baker City has been a vital point of trade between Portland and Salt Lake City since 1874. At the Farewell Bend State Park, the remains of wagon ruts from the beginning years of the Oregon Trail can still be admired. Museums such as the Eastern Oregon Museum and Baker Heritage Museum focus on Baker City’s role in the Oregon Trail. There are many more things to admire in eastern Oregon’s basecamp, so why not book a room in the historic Geiser Grand Hotel.
There are many beavers to be found in Oregon, hence why it is called the Beaver State. Thus, on your journey to the ten whimsical towns to visit in Oregon, you might come across these bucktoothed lumberjacks going about their usual routine. Regardless of whether you are visiting locations like Ashland for Shakespeare, Astoria for its references to The Goonies, or Joseph for its alpine heights, you will no doubt leave these destinations with fond and whimsical memories. Begin or end your adventures in Oregon, one of the most nature-filled and least-urbanized state in America.
