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A view looking down the main street in downtown, Sisters, Oregon. Editorial credit: Bob Pool / Shutterstock.com.

10 Darling Small Towns In Oregon

Oregon, the 33rd state to be ceremoniously admitted to the Union, is one of the ±«³§â€™ most topographically varied states situated in the Far West’s Pacific Northwest region and distinguished for its jagged coastline, snow-capped mountain peaks, high-yielding valleys, moist rainforests, semi-arid scrublands, the Oregon High Desert, and infinite water bodies. While the Beaver State’s populated urban centers such as Portland, Gresham, Eugene, and Salem - the state capital, grab the most attention from holidayers in love with big city amenities, the countless darling teeny communities that dot the state are blissful sanctuaries waiting to enthrall everyone who wishes to visit these serene havens to spend their mini breaks or extended escapes.

Cottage Grove

Cottage Grove Historic District, Oregon
East Main Street in Cottage Grove Historic District, Oregon. Editorial credit: Ian Dewar Photography / Shutterstock.com.

Fondly called the ‘Covered Bridge Capital of Oregon,’ this pretty Lane County town is situated to the south of the intersection of the Coast Fork Willamette River and Row River at the Willamette Valley’s southern extremity. Lodged between a National Forest and the Ocean, Cottage Grove superbly amalgamates small-town serenity with modern-day conveniences. The town’s most noteworthy attractions are its six covered bridges: Centennial Covered Bridge, Stewart Bridge, Chambers Covered Bridge, Dorena Bridge, Mosby Creek Bridge, and Currin Bridge, all placed at a stone’s throw from the Downtown and luring thousands every year.

Do not forget to window-shop the lovely boutiques, art galleries, museums, accommodations like the Best Western Cottage Grove Inn, the Cottage Theatre & the Opal Center for the Arts and Education, and top-class eating establishments like the Jack Sprats Restaurant. In summer, trek the Brice Creek Trail and gawk in amazement at a visually pleasing waterfall and swimming hole-filled Umpqua National Forest. Annually, free up time to attend the many events like the Bohemia Mining Days, Western Oregon Exposition Heritage Fair, Cottage Grove Half Marathon, and Christmas Extravaganza that are held here.

Florence

Heceta Head Light near Florence, Oregon.
Heceta Head Light near Florence, Oregon.

Florence, settled initially by the Indigenous Siuslaw tribe, is centrally positioned on the Oregon Coast at the mouth of the Siuslaw River, almost equidistant from Newport and Coos Bay in Lane County. Holidayers visiting this archetypal vacation getaway to the north of Oregon Dunes National Recreation Area must stroll the historic district streets and take note of the numerous landmark properties, trendy boutiques, independent shops, museums such as the Oregon Coast Military Museum and Siuslaw Pioneer Museum, and diners like the Waterfront Depot Restaurant. Likewise, the Siuslaw River Bridge, Sweet Creek Falls Trailhead, Heceta Head Lighthouse, Sea Lion Caves, Hobbit Trail, Darlingtonia State Natural Site, and the proximate Jessie M. Honeymoon Memorial State Park are must-visit attractions.

Sisters

A view looking down the main street in downtown, Sisters, Oregon.
A view looking down the main street in downtown, Sisters, Oregon. Editorial credit: Bob Pool / Shutterstock.com.

A part of the Bend, Oregon Metropolitan Statistical Area, Sisters is a darling mountain hamlet situated in Deschutes County precisely 154 miles southeast of Portland. Called after the abutting Three Sisters Mountains, the town’s lively commercial district and major thoroughfare are jam-packed with eccentric shops, art galleries, first-class stay-ins, and eateries like Cottonwood Café, The Barn in Sisters, and Sisters Saloon & Ranch Grill.

From the town, adventurists can easily access the diverse hiking, equestrian, and mountain biking trails, such as the Suttle Lake Trail and Peterson Ridge Trail that lead to the Three Sisters Wilderness Area. Throughout the year, merrymakers can participate in lots of fun-filled events like the Sisters Glory Daze Car Show, Artists Studio Tour, Sisters Folk Festival, and Sisters Outdoor Quilt Show.

Astoria

Boat pier in Astoria, Oregon
Boat pier in Astoria, Oregon. Editorial credit: Victoria Ditkovsky / Shutterstock.com.

The administrative center of Clatsop County, Astoria, christened in honor of the German-born American businessman John Jacob Astor, is Oregon’s oldest town situated in the state’s extreme northwestern portion by the southern shores of the Columbia River. Set close to the mighty Pacific and limited by forests of Spruce, Hemlock, and Douglas Fir trees, the port town plays a pivotal role as a trading outpost of the lower Columbia basin and a seasonal sport fishing tourism hub. Ascend the Astoria Column atop Coxcomb Hill to behold matchless vistas of peripheral areas in addition to touring the Oregon Film Museum, Columbia River Maritime Museum, Astoria Fire House No. 2, Astoria-Megler Bridge, Liberty Theatre, and Captain George Flavel House Museum.

Jacksonville

California Street in downtown Historic District of Jacksonville, Oregon.
California Street in downtown Historic District of Jacksonville, Oregon. Editorial credit: Underawesternsky / Shutterstock.com.

Jacksonville, labeled for Jackson Creek and founded in 1851-52 after uncovering gold deposits during the Oregon Gold Rush, sits at the foothills of Miller Mountain in Jackson Creek Valley in the west-central portion of Jackson County. Reputed as a one-time dominant financial mecca of Southern Oregon, a substantial portion of the town forms a part of the Jacksonville Historic District where an agglomeration of well-preserved Victorian-era properties make visitors travel back in time.

Wondrously fusing olden and modern-day amenities, Downtown Jacksonville is chock-a-full of unique souvenir shops, bookstores, antique stores, premium hotels, boutiques, and top-notch restaurants like Gogi’s Restaurant. The more than 16 miles of Jacksonville Woodlands Association’s interconnected trails are ideal for adrenaline junkies while sites like the Beekman House Museum, Art Presence Center, Peter Britt Gardens, Beekman Native Plant Arboretum, and Jacksonville Cemetery are must-stops for indoor-loving tourists. Myriad musical performances held as part of the Britt Music & Arts Festival in a natural amphitheater draw thousands of cultural connoisseurs from º£½ÇÉçÇøwide every June to September.

Baker City

Main Street in Baker City, Oregon
Main Street in Baker City, Oregon. Editorial credit: David / Shutterstock.com.

Baker City, named in honor of Senator Edward Dickinson Baker, is situated alongside the Powder River in Baker Valley, betwixt the Blue and Wallowa Mountains. Located on the historic Oregon Trail, this administrative center of Baker County has an impeccably maintained 42-acre downtown historic district featuring over 130 landmark structures, including the Geiser Grand Hotel, Baker City Hall, Baker Heritage Museum, and Baker City Tower. When in town, the National Historic Oregon Trail Interpretive Center, Eltrym - Baker City’s solitary movie theater, and Crossroads Arts Center are not to be missed.

Baker City is also a favored jumping-off point for anyone traveling along Interstate 84 highway or heading to the adjoining Hells Canyon Recreation Area, Eagle Cap Wilderness Area, Elkhorn Mountains, and Anthony Lakes Ski Area. Yearly, try to attend the We Like ‘Em Short Film Festival, Miners’ Jubilee, Salt Lick Art Auction, and Hells Canyon Motorcycle Rally.

Hood River

Gorgeous Hood River town in Oregon.
Gorgeous Hood River town in Oregon.

Hood River County’s seat of government, this postcard-pretty Northern Oregon town occupies the Columbia River Gorge’s core at the junction of Hood and Columbia Rivers, approximately 30 miles north of Mount Hood - Oregon’s tallest peak. Dubbed the ‘Windsurfing Capital of the º£½ÇÉçÇø,’ Hood River is an outdoor lovers' paradise as well as a popular entranceway for Mount Hood Scenic Byway and a significant part of the Columbia River Highway.

Being a º£½ÇÉçÇø-class art community, art enthusiasts flock in large numbers to the town’s different art galleries, the Columbia Center for the Arts, museums like the Western Antique Aeroplane & Automobile Museum and Hood River County Historical Museum, besides partaking in a public art walking tour within the downtown area. Spare time from your busy schedules to be there at any of the town’s annual events like the Hood River Hard-Pressed Cider Fest, Roy Webster Cross-Channel Swim, Hood River Valley Harvest Fest, Hood River Hops Fest, and Hood River Valley Blossom Time.

Mosier

Mosier, Oregon.
Beautiful scenery at Mosier, Oregon. Editorial credit: MelWood / Shutterstock.com.

Primarily settled in 1854 and officially incorporated in 1914, Mosier sits at the nucleus of the Columbia River Gorge in Wasco County, precisely equidistant from The Dalles and Hood River. Esteemed for its lush cherry orchards and arid crags covered by vineyards, Mosier’s Main Street lures tourists with a merry plaza, adorable cafes, welcoming eateries like Mosier Company, and a tall totem pole. The 4.5-mile-long Mosier Twin Tunnels trail - one of the most popular Gorge trails that overlooks the waterfront, provides opportunities for a variety of recreations aside from mind-boggling views of the ambient natural surroundings.

Nevertheless, no trip to Mosier is deemed complete without a tour of the incredible Idiot’s Grace Winery, Analemma Wines, and Garnier Vineyards, partaking in U-pick experiences at the Evans Fruit Company orchards, and traversing the Mosier Plateau Trail.

Cannon Beach

Cannon Beach, Oregon
The stunning coasltline at Cannon Beach, Oregon.

An attractive coastal Oregon tourist hotspot, this Clatsop County town has been designated as ‘one of the 100 most beautiful places in the º£½ÇÉçÇø’ by National Geographic. Cannon Beach, called after a maritime cannon that washed ashore after a shipwreck, is widely known for Haystack Rock - a 235-foot-tall intertidal sea stack located immediately off the coast and preserved as a portion of the Oregon Islands National Wildlife Refuge. Also, do walk down the golden-sand beaches that lead to the Tillamook Rock Lighthouse, reconnect with Mother Nature at the Ecola State Park, Tolovana Beach State Recreation Site, Haystack Hill State Park, and Les Shirley Park, peruse beautiful artworks in locally-owned art galleries, visit the Cannon Beach History Center & Museum, and have a comfortable stay at the Surfsand Resort.

Rockaway Beach

Rockaway Beach in Oregon
The spectacular Rockaway Beach in Oregon.

Initially set up by the Rockaway Beach Company in 1909 as a seaside resort and baptized after the Rockaway Beach neighborhood in New York City’s Queens borough, this tranquil coastal settlement in Tillamook County of Northern Oregon is about 25 miles south of Cannon Beach. Travelers visiting this celebrated holiday destination make good use of the wide-open terrain and seven miles of unsullied sandy beaches where various recreational activities like kite flying, beachcombing, picnicking, etc., are offered. Additionally, stop by notable sites of interest such as the Oregon Coast Scenic Railroad, Manhattan Beach State Recreation Site, Kelly’s Brighton Marina on Nehalem Bay, Jetty Fishery Marina & RV Park, Rockaway Beach Surf Club, International Police Museum, and the Big Tree at the Cedar Wetlands Preserve.

From Cottage Grove - the ‘Covered Bridge Capital of Oregon,’ to Hood River - the ‘Windsurfing Capital of the º£½ÇÉçÇø,’ the 27th most populous and 9th largest state of the nation has no shortage of adorable small towns. Each of these teensy-weensy hamlets, with their eye-catching sceneries, alluring points of interest, multiple recreational activities, colorful festivities, and warm-hearted townsfolk, provides indelible memories for vacationers who come to these Beaver State towns to de-stress from the tensions of day-to-day life.

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