The Best Small Towns in Oregon to Chill Out In 2024
Few states in America promote the primordial forests and ancient landscapes of the past than Oregon. Outside Portland’s urban networks are mountains, forests, and even deserts that have barely changed long before the two explorers, Meriwether Lewis and William Clark, pitched their final camps in Oregon. And it is within these great lands that you will find some of the best small towns in Oregon to chill out in 2024. At Florence and Cannon Beach, you can soak in the cool sprays and shade of the Pacific Ocean. At The Dalles and Baker City, one can traverse the iconic Oregon Trail. And at Hood River and Yachats, you will fall in love with both the nature and culture of these humble small towns in the Beaver State. So sink your teeth and take a bite out of the best small towns in Oregon to chill out in 2024.
Florence
Do not be mistaken this small town with the city of Florence in Italy. The small town of Florence in Oregon happens to be “Oregon’s Coastal Playground” because of the Stellar sea lions migrating at the Sea Lion Caves near the mouth of the Siuslaw River. Notwithstanding this mammalian spectacle, Florence also contains the 19th-centruy Heceta Head Lighthouse, a great vantage point to sightsee seabirds and whales on the Pacific Ocean. The best time to actually see these migrating whales is around March 23 to 31. If you prefer more land-based activities, then journey across the Siuslaw River and into he Oregon Dunes National Recreation Area, where you can experience thrilling horseback rides or buggy rides across miles of sand dunes. Do not fret about where you will be staying in the cold evenings, because fine establishments like the Old Town Inn, River House Inn in Florence, and Driftwood Shores Resort have you covered.
Hood River
Let the wind sweep you off your feet in the exhilarating town of Hood River. Situated near the adventure-idyllic Mount Hood and the Columbia River Gorge, those seeking to pump their adrenaline can revel in windsurfing activities from Mount Hood’s pristine slopes and summit. To reach Mount Hood, you ought to traverse the Timberline Trail which circumnavigates the whole mountain. Or you can take the Coopers Spur Trail which leads to the highest possible and accessible point on Mount Hood. Regardless of which path you take, you will certainly find many jumping points for you to begin your windsurfing journeys through Hood River’s skies. If you prefer a more land-locked exploration, then delve into the Columbia River Gorge where numerous waterfalls and camping sites are certain to soothe your city-worn soul. If you ever need a place to stay in Hood River, look no further than to the Hampton Inn & Suites Hood River or Columbia Gorge Hotel and Spa.
Cannon Beach
Approximately 90 minutes from the city of Portland, have a blast at the shores of Cannon Beach. For years, thousands of tourists have flocked to Cannon Beach for its alluring waters and splendid sand. Most of all, they take photos—groupies or selfies—of the 235-foot-tall Haystack Rock, a natural monument to Cannon Beach’s magical atmosphere.
The town was named after a naval cannon found on those same shores, the last remains of a shipwreck long ago. These days, Cannon Beach sponsors many natural attractions around it, such as Ecola State Park and Arcadia Beach. The latter, specifically, contains tide pools that are perfect for wading around. For those of you who desire to spend a longer vacation in Cannon Beach, then book a room at The Wayside Inn, Beachcomber Vacation Home, Argonauta Inn, or AvantStay.
Baker City
Baker City has been a major waystation of trade and commerce between Portland and Salt Lake City in Utah since 1874. Even though it is sandwiched between the Wallowa Mountains and the Elkhorn Mountains—both part of the Blue Mountain Ranges—Baker City happens to be called “eastern Oregon’s basecamp” because of its location along the historic and fabled Oregon Trail. One might come across the remnants and relics of old-school wagon ruts at the Farewell Bend State Park when the Oregon Trail bustled with travelers. You can always learn more about Baker City’s trailblazing past at the Baker Heritage Museum and the Eastern Oregon Museum. But for those of you who are exhausted and weary from all the good travels, you can stay a while at the historic Geiser Grand Hotel.
Joseph
Want a taste of Switzerland in the far western corner of American? Then venture into the humble dwellings of Joseph, the “Little Switzerland of America.” With its chilly spot on the Wallowa Mountains that overlook Hells Canyon, you will be feeling like you are in the Alps of Europe for sure. Interestingly enough, the town’s name is based off of Chief Joseph of the Nez Perce tribe. An annual Tamkaliks celebration honors this proud and noble chieftain and his people. The Wallowa County Museum gives a detailed explanation regarding Joseph’s inception. As for the Wallowa County Farmers' Market, you can find all manner of ripe and delicious produce from Oregon’s bountiful harvests. You can delve into Hells Canyon or fish and kayak along Wallowa Lake. The more adventurous of you might fancy the Eagle Cap Wilderness to explore more of Joseph’s outdoors. Once your feet get tired from all the walking, settle down at the Bronze Antler Bed & Breakfast, Eagle Cap Chalets, Flying Arrow Resort, or Trouthaven Resort.
Yachats
Yachats (pronounced yah-hots) is the type of place for surfers and beachgoers who wish to brave more treacherous waters. As a matter of fact, Yachats is a Siletz phrase meaning "dark water at the foot of the mountain,” and this is seen in the dark rock formations at the Yachats Ocean Road State Natural Site. There is also Thor’s Well, a natural drainage hole that siphons and suctions off the waters of the Pacific Ocean into an unknown destination. For those of you who are hesitant to visit these watery treacheries, then you take the Ya’Xiak (yah' khik) Trail and Amanda's Trail towards Cape Perpetua, the highest vantage point on the Oregon Coast. For accommodations, seek out an opening or more at the Overleaf Lodge & Spa, Ocean Cove Inn, or the Yatel Motel.
Silverton
Approximately 45 miles from Portland, you will come across “Oregon’s Garden City,” the flowering town of Silverton. Over 80 acres of parkland and fields comprise Silverton’s Oregon Garden, where all sorts of horticultural wonders and floral species are in perpetual bloom. Toddlers and juveniles can revel in the Children's Garden while animals can frolic about in the Pet-Friendly Garden. You might also fancy attending a handful of cultural and yearly events in the Oregon Garden, such as the Arts in the Garden. Elsewhere, newcomers to Silverton can trek through the Silver Falls State Park, where the "Trail of Ten Falls” gives you a scenic appreciation of the many waterfalls in Silverton. Should you wish to see more of Silverton’s natural splendors, you ought to keep your belongings safe and sound at the Oregon Garden Resort, the Silverton Inn and Suites, or Edward Adams House B&B.
Ashland
Nothing is rotten in the state of Oregon, especially in the small town of Ashland. As a patron of all things artistic and cultural, Ashland houses as the Ashland Artworks Gallery and the Schneider Museum of Art, where many of Oregon’s majestic artworks are in fitting display. The many landmarks around Ashland, too, has their aesthetic qualities to appease the most refined of souls, as best seen in the Lithia Park and Mount Ashland. However, this small town deep in the Rogue River Valley and at the base of Siskiyou Mountain is renowned for keeping William Shakespeare’s genius and literature thriving in Oregon. From February through November, the townsfolk commemorate the beloved Oregon Shakespeare Festival where everyone—from townsfolks to newcomers, actors to audience—can either watch or even participate in the Bard’s many influential plays. So if you desire a resplendent domicile to call a temporary home in Ashland, choose one of the many grand lodgings in Ashland such as the Swank & House, The Winchester Inn, StayAshland, or The Bard’s Inn Hotel.
Sisters
The Cascade Mountains surround the quaint town of sisters in Oregon’s high-desert area. The town itself derived its name from the three volcanic peaks nearby, and these days, Sisters is a great launching point towards the Three Sisters Wilderness. From there, one can take memorable and serene photos of magnificent vistas and desert lands from an impressive view. Outdoors lovers can brave the ponderosa pine trees of the Deschutes National Forest. Meanwhile, at Smith Rock State Park, one can gallivant through 650 acres of arid and unyielding deserts. Consider taking the Pacific Crest Trail to see more of Sisters’ dynamic and ferocious landscapes. Most of all, do not miss out on the Sisters Rodeo, “The Biggest Little Show in the World” every year from June 5 to 9. For those of you invested in Sisters, you can luxuriate and relax at either the Best Western Ponderosa Lodge, the Black Butte Ranch Vacation Rentals, or the Long Hollow Ranch.
The Dalles
The Dalles has been the epicenter of trade and transportation for Oregon’s Native American cultures for 10,000 years. As such, The Dalles is considered one of the oldest inhabited settlements in Oregon. As a town about 20 miles east of Hood River, one can traverse the Columbia River Gorge to visit this vibrant and thriving community that has accommodated numerous individuals for eons. One can learn about the Lewis and Clark Expedition in 1805 at the Columbia Gorge Discovery Center and Museum, whereas the Fort Dalles historic site exhibits a replica of an 1850s US Army Outpost which immortalizes The Dalles’ pioneer history. For a better or more aesthetic appreciation of the Columbia River Gorge, you gawk at the different artworks and interpretations of the landscape at the Maryhill Museum of Art. You will not feel unwanted in The Dalles, especially in welcoming lodgings such as the Cousins Country Inn, Comfort Inn Columbia Gorge, or Celilo Inn.
Astoria
Astoria has been called the “little San Francisco” because of its big, seaside atmosphere and energy in spite of its smaller size. However, Astoria is more notably renowned for being the film setting for the classic movie, The Goonies. Those familiar with The Goonies will certainly feel pangs of nostalgia and recognition while strolling through the Astoria Riverwalk which lines the Pacific Ocean and the Columbia River. For those of you who are eager to know more about Astoria aside from its film-suitable locale, you can know more about its heritage at the Columbia River Maritime Museum. You can also tour the Buoy Beer Company and Fort George for a deeper inference of Astoria’s maritime past. Some of you might fancy delicious seafood meals by taking the Astoria Riverfront Trolley. Last but not least, excellent accommodations like the Astoria Riverwalk Inn and the Best Western Long Beach Inn will certainly keep you safe and sound in Astoria.
The Takeaway
Sometimes, the less-traveled roads lead to more exciting destinations than the well-trodden paths. This is especially true for the Beaver State of Oregon, home to some of the best small towns to chill out in 2024. Each of these towns offer innumerable treasures, experiences, and memories that will keep you wanting to explore more of the region. From the dynamic landscapes of Sisters to the theater-loving community of Ashland, there is no deficit of destinations to make you fall in love with Oregon’s chill small towns. Embark on your own journey through Oregon, and allow the Pacific Ocean’s winds take you to some of the best small towns in Oregon this 2024.
