8 Charming Small Towns in Oregon

Mount Hood and valley view from Mount Hood Organic Farms, Hood River Valley, Oregon.
VWPics/Universal Images Group via Getty Images

Oregon is filled with beauty, with charming little communities dotting the great state between larger, more popular cities like Portland, Salem, and Eugene. Many of these places have a unique history and make for a fun-filled stay for tourists who stop in and grab a bed and breakfast for a night or two. So if you’re planning a trip to this U.S. state, hoping to retire, or are a local looking for a day trip, read on to discover our list of eight charming small towns in Oregon.

Yachats

The first thing to know about this coastal town is how it’s pronounced: Yah-hots. One of the most attractive features of this hidden gem and the surrounding area is that it’s rarely ever crowded, even in the peak of summer when inland temperatures are soaring and Willamette Valley residents flee to the coast. The main attraction here is Cape Perpetua, located just outside town. The headland rises over 800 feet at its highest point, giving visitors the opportunity to see 60 kilometers out to sea on a clear, sunny day. Walk the 26 miles of hiking trails or stay closer to the ground to seek out the gray whales that feed along the coast. The town itself is a typical cute coastal town, featuring art galleries, a vibrant live music scene, and small cafes.

Jacksonville

Our top small town in Oregon is one non-residents are unlikely to have ever heard of – yet Jacksonville immediately casts a spell on nearly everyone who visits. The town was founded on a gold rush and for thirty years it boomed. But in 1884, the railroad passed Jacksonville by, and as the town’s fortunes declined, it essentially created a place frozen in time. Downtown looks like it might be a Wild West movie set come to life, except that the shops are selling trendy clothes, unique trinkets, and craft coffee. After marveling at the wonderfully preserved buildings and the general hospitality of the town, take the opportunity to see what’s bringing Jacksonville to life once again. The nearby Applegate Valley Wine Trail showcases 18 vineyards, most of which provide a relaxing atmosphere and offer plenty of time and attention to teaching visitors about their delicious vino (and pouring samples, of course).

Hood River

Modern day Oregonians are practically required by law to enjoy outdoor activities. But one visit to this hamlet and any non-natives will realize this is no hardship. Hood River is possibly the best small town in the state (and the most beautiful too!), with the Columbia River stretching along its banks and Mt. Hood’s peak towering above. Waterfront Park is guaranteed to be filled with walkers, joggers, and bikers, while the river below teems with windsurfers. Hood River calls itself the “Windsurfing Capital of the World” and accordingly has a dedicated harbor just for those learning the sport. Opportunities for kitesurfing, kayaking, and paddle boarding also draw thousands of visitors. After working up an appetite, visiting one of the town’s many delicious restaurants is a must. With so many fruits and veggies grown in the surrounding valley, local cuisine is a treat.

Cottage Grove

The southern Willamette Valley is filled with pockets of serene beauty. The gorgeous rolling hills, lush fields, and clear rivers are made all the more special when an intrepid explorer comes upon one of Oregon’s many covered bridges. Cottage Grove, the “Covered Bridge Capital of Oregon,” has six of these bridges near the city, all distinct and equally captivating. Get some of the best glimpses of the landscape by biking the Row River Trail, which shows off a couple of those covered bridges. The trail was once a railroad track, made famous in the 1986 movie Stand By Me, particularly the section crossing Mosby Creek, which is made familiar from the opening scene of the film. The historic theme continues in central Cottage Grove, which features impressive murals decorating the well preserved buildings.

Astoria

Fort Astoria, built for the American Fur Company in 1811, was the first U.S. permanent settlement on the Pacific Coast. Furs no longer drive the economy of course, but that pioneering spirit remains. The outpost on Oregon’s far northwestern edge was settled by Nordic fisherman and Chinese cannery workers, whose influences can still be felt today, everywhere from the boats in the harbor to the refurbished warehouses along the water. Astoria is considered the prettiest small town in Oregon where visitors can wander through the old fashioned downtown, ride the streetcar along the waterfront, or stop off at art galleries, microbreweries, and gourmet ice cream shops in the former cannery district. A trip up Astoria’s steep hills leads to the Astoria Column, whose observation deck provides an amazing panorama of the city, river, ocean, and countryside. Finally, movie lovers will get a kick out of seeing sites spotted in films such as Kindergarten Cop, Free Willy, and – Astoria’s most beloved gem – The Goonies.

McMinnville

McMinnville may have popped up around a flour mill, but it’s grape barrels that keep the economy going these days. Yamhill County is at the heart of Oregon’s ever burgeoning wine industry, and McMinnville is a great jumping off point for the nearly 200 wineries in the area. Unique tours abound, from horseback riding between tasting rooms to a hot air balloon ride that lets people truly appreciate the beauty of the valley. In McMinnville itself there are 13 winemakers and, because this is Oregon, 6 craft breweries for anyone craving something a little hoppier. The historic downtown also features several excellent restaurants featuring the local wines. For those who like a little quirkiness served alongside their Pinot Noir, McMinnville holds an annual UFO festival in May, complete with an alien costume parade, to celebrate a famous UFO sighting that occurred in 1950.

Pendleton

Situated in northeast Oregon along the banks of the Umatilla River, Pendleton has long been defined by its textiles. Pendleton Woolen Mills was founded in 1868, and its wares are iconic Americana today, from the classic plaid shirts to the Native American inspired designs on its blankets. The Tamástslikt Cultural Institute at the nearby Umatilla Reservation provides more perspective on the Native American tribes that have been living in Pendleton for a long time, with displays showing the region’s history through the eyes of the Walla Walla, Cayuse, and Umatilla Tribes. The tribes also participate in the town’s most famous event, the Pendleton Round-Up, founded in 1910 to celebrate frontier culture. Held annually during the second week of September, the Round-Up features parades, a Pow Wow Dance Competition, and traditional rodeo events like steer roping and barrel racing. Even if the rodeo’s not in town, Pendleton still provides a good glimpse into Oregon’s frontier past. Pendleton is also one of the cheapest towns to live in Oregon, according to data pulled from the U.S. census, so if you’re looking for affordable, stop into Pendleton.

Baker City

Anyone who grew up playing the old computer game “Oregon Trail” will feel a little thrill when visiting this small town in the eastern part of the state. Flagstaff Hill, with its views of the Blue Mountains, signified that the long journey undertaken by those wagon trains was finally coming to an end – although many would still need to raft their way down the Columbia River. The National Historic Oregon Trail Interpretive Center atop the hill offers plenty of information for history nuts to geek out about, including artifacts and replica wagons. Authentic wagon ruts, however, can be seen outside, a reminder that this wasn’t a game for the thousands of emigrants that traveled the trail. Further evidence of how difficult life was for those new Oregonians can be seen at the excellent Baker Heritage Museum, while the Chinese cemetery is a reminder of those who gave so much to help build the town.

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