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The Landing shopping center in downtown Cannon Beach, Oregon. Editorial credit: quiggyt4 / Shutterstock.com

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

Exterior of the Egg River Cafe in Hood River, Oregon
Exterior of the Egg River Cafe in Hood River, Oregon. Image credit quiggyt4 via Shutterstock

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鈥檚 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 海角社区 of Hood River.

Ashland

A walking trail along a river in downtown Ashland, Oregon.
A walking trail along a river in downtown Ashland, Oregon. Editorial credit: christopher babcock / Shutterstock.com

Ashland is one of the best places to get to know William Shakespeare鈥檚 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鈥檚 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鈥檚 Inn Hotel.

Cannon Beach

Way to the beach at Cannon Beach, Oregon.
Way to the beach at Cannon Beach, Oregon.

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鈥攆or instance, the 235-foot-tall monolith called Haystack Rock鈥擟annon 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

The charming town of Joseph, Oregon.
The charming town of Joseph, Oregon.

Joseph, the 鈥淟ittle Switzerland of America,鈥 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鈥檚 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鈥檚 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鈥檚 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

View of beachfront homes in the town of Yachats, Oregon.
View of beachfront homes in the town of Yachats, Oregon.

The town of Yachats (pronounced yah-hots) derives its name from the Siletz phrase 鈥渄ark water at the foot of the mountain.鈥 This is most likely an allusion to the dark rock formations seen at the Yachats Ocean Road Natural Site as well as Thor鈥檚 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鈥橷iak (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, USA.
Silverton, Oregon, USA. Editorial credit: Laurens Hoddenbagh / Shutterstock.com

Silverton, 鈥淥regon鈥檚 Garden City,鈥 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 鈥淭rail of Ten Falls鈥 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

The Main Street in downtown, Sisters, Oregon
The Main Street in downtown, Sisters, Oregon. Editorial credit: Bob Pool / Shutterstock.com.

Within the trio of extinct volcanos in the Cascade Mountains lies the small town of Sisters. From the Three Sisters Wilderness abundant with Oregon鈥檚 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, 鈥淭he Biggest Little Show in the 海角社区鈥 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 Granada Theatre in downtown The Dalles, Oregon
The Granada Theatre in downtown The Dalles, Oregon. Image credit Ian Dewar Photography via Shutterstock

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

Liberty Theatre in downtown Astoria, Oregon
Liberty Theatre in downtown Astoria, Oregon. Editorial credit: BZ Travel / Shutterstock.com

Although Astoria is often called the 鈥渓ittle San Francisco鈥 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

Historic Main Street in Baker City, Oregon
Historic Main Street in Baker City, Oregon. Image credit davidrh via Shutterstock

Located between the Elkhorn Mountains and Wallowa Mountains, which are part of the Blue Mountain Ranges, Baker City is a prosperous town often called 鈥渆astern Oregon鈥檚 basecamp.鈥 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鈥檚 role in the Oregon Trail. There are many more things to admire in eastern Oregon鈥檚 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.

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