8 Small Towns That Capture Oregon’s Quirky Charm

Portland is high on many traveler’s lists, but what about the rest of the great state of Oregon? There’s beauty to be found in every corner of the state, from the rugged Pacific coastline to the desolate splendor of the eastern desert. More than that, though, there’s quirkiness scattered throughout the state, displaying Oregon’s unique history in all its various guises. Read on to find out the eight small towns that best capture Oregon’s quirky charms.

8. McMinnville

McMinnville may have grown up around a flour mill, but it’s grape barrels that keep the economy spinning 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 tour possibilities abound, from horseback riding between tasting rooms to a hot air balloon ride that lets visitors truly appreciate the beauty of the valley. In McMinnville itself there are 13 winemakers and, because this is Oregon, 6 craft brewers for anyone craving something a little hoppier. The historic downtown also features several excellent restaurants showcasing 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 alien costume parade, to celebrate a famous UFO sighting that occurred in 1950.

McMinnville oregon

7. Yachats

The first thing to know about this coastal town is how it’s pronounced: Yah-hots. The next thing to know is: don’t tell anyone else about this tiny gem. One of the most attractive features of the town and its surrounding area is that it’s rarely ever crowded, even in the dead 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 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 Oregon coastal town, featuring art galleries and local crafts for sale.

Yachats lighthouse oregon

6. 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 over 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.

Baker City Oregon wagon

5. Hood River

Modern day Oregonians are practically required by law to enjoy participating in outdoor activities. But one visit to Hood River and any non-natives will realize this is no hardship. The town is possibly the most scenic in the state, with the Colombia River stretching along its banks and Mt. Hood’s triangular form towering above. Waterfront Park is practically 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 paddleboarding also draw thousands of visitors. After working up an appetite with so much activity, visiting one of the town’s many delicious restaurants is a must. With so many fruits and veggies grown in the surrounding valley, make like a local and eat what’s grown nearby.

Hood River Oregon

4. Cottage Grove

The southern Willamette Valley is filled with pockets of quiet beauty. The rolling hills, the lush fields, the clear rivers…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 all captivating. Get some of the best glimpses of the landscape by biking the Row River Trail, which also 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, familiar from the opening of the movie. The historic theme continues in central Cottage Grove, which features impressive murals decorating the well preserved buildings.

covered bridge  Cottage Grove oregon

3. 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 wears 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 Indian Reservation provides more perspective on the Native American tribes that have long called Pendleton their home, 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 mentality.

Pendleton round up oregon

2. 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 steer the economy, of course, but a sense of 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. 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.

Astoria oregon

1. Jacksonville

Our top small town in Oregon is one non-residents are unlikely to have ever heard of – yet Jacksonville immediately casts an enchantment on nearly everyone who visits. The town was founded on a rush of gold, and for thirty years it positively 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 the shops are selling trendy clothes, unique trinkets and excellent 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 more. The nearby Applegate Valley Wine Trail showcases 18 vineyards, most of which provide a calm atmosphere and offer plenty of time and attention when teaching visitors about their delicious wares.