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

12 of the Most Charming Towns in Oregon

The state of Oregon, commonly known as the Beaver State, was admitted into the United States as the 33rd state in February of 1859. Since that time, visitors from all over have referred to this pastoral area within the Pacific Northwest as having some of the most pleasant small towns and villages, possibly due to its friendly residents and the hometown feelings these people inspire. From the town of Astoria in Clatsop County to the town of Enterprise in Wallowa County, here are a dozen of the most charming, amiable towns across the state of Oregon that will urge you to revisit over and over.

Astoria

The Liberty Theater and downtown Astoria. Editorial credit: Bob Pool / Shutterstock.com
The Liberty Theater and downtown Astoria. Editorial credit: Bob Pool / Shutterstock.com

This quaint town of around ten thousand people, known for being the oldest town in Oregon, has a variety of festivals that cater especially to visitors. The Astoria Warrenton Crab, Seafood, and Wine Festival takes place every April. The Scandinavian Midsummer Festival, held every June for the last fifty-plus years, welcomes guests to take part in the town’s Scandinavian heritage. The Clatsop County Fair, occurring in August, attracts over ten thousand people yearly. There are also several dining and lodging choices in Astoria, like the Silver Salmon Grille, which serves a tasty selection of seafood straight from the ocean, and Rose River Inn B&B, offering free breakfast to their guests every morning.

Hood River

Mt. Hood from Panorama Point in Hood River, Oregon.
Mt. Hood from Panorama Point in Hood River, Oregon.

Famous for a plethora of natural amenities and attributes, like Columbia River Gorge and Horsetail Falls, the town of Hood River is also home to the Western Antique Aeroplane and Automobile Museum, which showcases a 1902 Wright Glider, a 1916 Sopwith Scout, and a 1929 Studebaker Commander 8, as well several other antique planes and motor vehicles. Along with an informative journey back into the annals of Oregon history, Hood River also offers a variety of events and festivals, like the Hood River Valley Harvest Fest, welcoming visitors to sample some of the best-grown local produce in the valley, and the Spring Break Snow Beach Festival taking place on nearby Mount Hood.

Florence

Beautiful view of Siuslaw river bridge and the river in historic old town Florence, Oregon, USA.
Beautiful view of Siuslaw River bridge and the river in historic old town Florence, Oregon, USA.

The quaint town of Florence, sitting along the estuary of the Siuslaw River on the coast of the Pacific Ocean, is a marvelous haven for natural beauty. Heceta Beach, the Sea Lion Caves, and the Jessie M. Honeyman Memorial State Park are some of the many wonders offered up to visitors each year. There are also many festivities in Florence, including the Rhododendron Festival, welcoming thousands of visitors each year to view the wondrous beauty of these magnificent flowers. Several seafood eateries and restaurants also await the intrepid traveler in Florence, like the Waterfront Depot Restaurant, which serves a mouth-watering crab-encrusted halibut, and the Florence Boardwalk Market, open every weekend and offering fresh, locally-grown produce all summer long.

Cannon Beach

Cannon Beach reflections at low tide.
Cannon Beach reflections at low tide.

Situated on the upper coast of Oregon, between Astoria and Tillamook, the idyllic town of Cannon Beach is home to a variety of attributes that provide the town with that keen sense of charm. Just south of the Columbia River estuary, this town of one and a half thousand permanent residents offers a slew of festivals that cater to visitors, including the Cannon Beach Sandcastle Contest, held each June since 1964, and the Earth & Ocean Arts Festival, occurring in the middle of September every year. There are also several establishments in town that offer that quaint, hometown touch, like Lighthouse Inn, which is a five-minute walk from downtown and only a couple minutes from the beach, where the famous 235-ft Haystack Rock can easily be photographed.

Sisters

Sunrise with horses on a foggy Black Butte Ranch meadow with the Three Sisters mountains in the background near Sisters, Oregon.
Sunrise with horses on a foggy Black Butte Ranch meadow with the Three Sisters mountains in the background near Sisters, Oregon.

The town of Sisters is another amiable, peaceful town that offers a vast variety of exhilarating views of nature at its best. Sahalie and Koosah Falls, Clear Lake, Proxy Falls, and Three Creek Lake all call the town of Sisters home. Plus, this town of around three thousand people offers several festivals and events throughout the year that welcome visitors from as far away as Maine and Florida. The Big Ponderoo Music and Art Festival and the Sisters Folk Festival take place every June and September, respectively, and the Harvest Faire draws over twelve thousand people each year, offering visitors over a hundred and fifty different booths, stalls, and tables to peruse at their leisure.

Yachats

Usa, Oregon, Yachats. Thor's Well.
Usa, Oregon, Yachats. Thor's Well.

Situated between the Siuslaw National Forest and the Pacific Coast, Yachats is home to a variety of festivals that welcome thousands of visitors every year. The La De Da Parade occurs every 4th of July. The Yachats Farmers Market is open from May to October yearly, offering a plethora of locally-grown, fresh produce. The Yachats Mushroom Festival, held in October, allows guests to experience a variety of different mushrooms, some of which only flourish in the area. Also, just north of Yachats Ocean Road State Park, a plethora of restaurants are aimed toward serving up some of the best seafood dishes available, including the Luna Sea Fish House, which not only offers a tasty Wild King Salmon but will also send you home with some fresh, raw salmon, sold by the pound on site.

Dundee

Vineyard in Dundee Oregon on a foggy morning.
Vineyard in Dundee, Oregon, on a foggy morning.

Surrounded by some of the most scenic, fertile vineyards in the northwestern United States, the town of Dundee is a verdant playground for those who love wine and, in particular, wine-tasting. Along with several wineries, including Torii Mor Winery, the Four Graces Winery, and Argyle Winery, there are at least an equal number of wine-tasting tours. Plus, in nearby Newburg, a mere two and a half miles away, there are a variety of great restaurants that excel in wine-pairing, including the Painted Lady and Rosmarino Osteria Italiana, which offers a five-course winemaker’s series. And, if you wish to stay for the evening or perhaps for the entire weekend, La Bastide Bed & Breakfast in downtown Dundee offers guests free wifi and a free breakfast the next morning.

Baker City

Baker City, Oregon, USA. Editorial credit: davidrh / Shutterstock.com
Baker City, Oregon, USA. Editorial credit: davidrh / Shutterstock.com

Baker City is a charming, pastoral oasis located between Malheur National Forest, Eagle Cap Wilderness, and Umatilla National Forest. Situated just below Wingville, this town of around ten thousand residents is cultural, historic, and natural, all blended into one. Yet, Baker City also has a variety of businesses and attributes that reach out and welcome guests from as far away as the Atlantic Ocean. Go Wild: American Adventures, based in Baker City, offers walking, hiking, fishing, and beer-tasting tours, and Sumpter Valley Railway presents the Cab Pass Program, which includes a ride on one of two locomotives (both steam-powered) from Baker City to Sumpter and back. Plus, in downtown Baker City, visitors can experience the taste of the area at several local eateries, including Latitude 45 Grille.

Brownsville

Old western style architectural Masonic Lodge building in the rural town of Brownsville, Oregon. Editorial credit: Michael Warwick / Shutterstock.com
Old western-style architectural Masonic Lodge building is in the rural town of Brownsville, Oregon. Editorial credit: Michael Warwick / Shutterstock.com

Perhaps known best for being the filming location of the movie “Stand By Me” and for being the home of the Moyer House, along with sixty other buildings from the mid-19th century, the town of Brownsville has a history all its own. Yet, this town of less than two thousand residents also has a welcome mat that outshines most others. Home to River Mist Gardens along the Calapooia River and the Living Rocks Studio, known for its Living Rock Art, Brownsville has a pleasant demeanor that cannot be beaten. There are several events held year-round in downtown Brownsville, including the City-Wide Garage Sale, the Antique Faire, and the Brownsville Farmers Market, which takes place every Thursday, all summer long, in Kirk Ferry Park.

Carlton

People walk the sidewalk in downtown Carlton, Oregon during the annual wine crush festival. Editorial credit: Dee Browning / Shutterstock.com
People walk the sidewalk in downtown Carlton, Oregon, during the annual Wine Crush festival. Editorial credit: Dee Browning / Shutterstock.com

Another charming, amiable town within Yamhill County, the town of Carlton is a haven for wine tasting, wine-making, and wine-pairing. Located approximately twelve miles away from Dundee, Carlton has at least as many vineyards and wineries as Dundee if you travel through the town of Newberg. Yet, this small town, claiming just over two thousand residents, offers a vast amount of attributes and activities not related to the growth and production of the grape as well. The Willamette Coast Ride, stationed in Carlton, presents a rare opportunity to go horseback riding along the Pacific coast. Plus, Carlton Fun Days, happening every year, offers a 5K race, a vintage car show, and a parade, as well as a large variety of individual vendors.

Jacksonville

Downtown Historic District brick buildings in Jacksonville, Oregon, USA. Editorial credit: Underawesternsky / Shutterstock.com
Downtown Historic District brick buildings in Jacksonville, Oregon, USA. Editorial credit: Underawesternsky / Shutterstock.com

The town of Jacksonville, named for Jackson Creek, which flows through downtown along with Daisy Creek, is perhaps best known for its downtown being listed on the U.S. National Historic Landmark in 1966. Yet, this quaint town of just over three thousand people has a plethora of amenities that assist with an amiable charm that keeps everyone talking. The trolley tours offer a forty-five-minute overview of the history of Jacksonville while showcasing several of the older buildings in town. The Britt Music and Art Festival features country, R&B, pop, and rock musicians, along with a variety of local artists. There are also several eateries in Jacksonville, like the Back Porch Bar & Grill and C St Bistro, both of which offer a choice of either indoor or outdoor seating.

Enterprise

Enterprise, OR, USA. Editorial credit: Ian Dewar Photography / Shutterstock.com
Enterprise, OR, USA. Editorial credit: Ian Dewar Photography / Shutterstock.com

Home of the Hells Canyon National Recreation Area and Rattlesnake Grade, the town of Enterprise might not seem charming based on these names. This is not the case, though. This town of about two thousand permanent residents is also home to the 1910 Historic Enterprise House B&B and the Barking Mad B&B Ranch, where you are welcomed pleasantly by the locals and can meet people from all around America. There are also a variety of festivals happening in Enterprise all year long, including Hells Canyon Mule Days and Wallowa County Fair. Wallowa County Fair, occurring at the beginning of August every year, showcases several events, including a 4-H Horse Show and a 4-H Dog Show.

So, in conclusion, whether you find yourself way up in the hills and mountains, among thick forest wilderness, or out along the rugged Pacific Ocean coast, there is something for everyone in and around these twelve charming Oregon towns. From amiable bed & breakfasts to quaint downtown historic districts, from majestic waterfalls to rustic, gurgling streams, these twelve towns within the northwestern corner of America cater to a wonderful sense of peace and tranquility that everyone craves.

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