7 Quirky Little Towns In Oregon

Oregon is filled with towns that embrace unusual attractions, offbeat traditions, and a sense of fun that sets each place apart. In spots like Tillamook and Gold Hill, visitors encounter curious landmarks, quirky events, and natural settings that reveal the state’s playful spirit. From a Sasquatch museum to a UFO festival and a race featuring pigs in Model-T Fords, these destinations offer memorable experiences for travelers who enjoy surprises, where strange sights and distinctive history create a one-of-a-kind adventure in the Pacific Northwest.

Tillamook

Tillamook is a cozy town with plenty of intriguing finds. The renowned Octopus Tree is a hotspot here, which is an oddly-shaped Sitka spruce tree with a bizarre formation that splits into smaller trunks. You can find the Octopus Tree at Cape Meares Lighthouse, as well as a stunning oceanic paradise full of sea lions, dolphins, and porpoises. If you crave a truly odd feature of Tillamook, however, consider the Pig-N-Ford Races, where you can find residents racing each other in vintage cars while carrying pigs. The community event has been a fan favorite at the Tillamook County Fair for 100 years.

History lovers may take a detour to Tillamook Air Museum, a World War II blimp hangar with the largest clear span wooden architecture in the world. Its aircraft collection and cockpit virtual reality experiences are sure to raise eyebrows. When it's time to refuel, try out Alice's Country House, a welcoming locale with the best comfort food and homemade desserts.

Gold Hill

Home to optical illusions and enchanting stops, Gold Hill is a must for odd itinerary travelers. The Oregon Vortex is what typically brings people to the Oregon Vortex House of Mystery, where you will find yourself in a crooked, distorted shack that defies logic and the laws of physics. For nature enthusiasts, Ti'lomikh Falls is a preserve featuring hiking trails that wind along river rapids and through an abundance of natural beauty.

Del Rio Vineyards is set against a gorgeous Rogue Valley backdrop and offers wine tastings within the Rock Point Stage Hotel. The charms and elegance of the locale provide the perfect venue for relaxing picnics and southern Oregon's largest vineyard views. For a different sipping experience, take a seat at The Teapot on Wheels, serving high tea by reservation and a selection of sweet and savory crepes.

Boring

Boring's reputation is quite contrary to its name. The North American Bigfoot Center has friendly knowledge and offers tours related to the mysterious, mythical beast, while believers and non-believers alike can enjoy the gift shop, which features themed housewares, toys, and unique souvenirs. You can also find the famous "Murphy" Sasquatch mascot standing tall at the museum.

For something a bit more mainstream but no less spectacular, Mountain View Golf Course offers 18 holes of well-groomed fairways and Cascade Range vistas from every tee. Oregon Blues has 5 acres of blueberry farms and seasonal u-picks, and Dolan Creek Farm is just as delightful, with its pumpkin patch, walking trails, petting farm, and tractor rides.

Sisters

Sisters is unique for its 1880s Old West ambiance. If you are visiting this quirky frontier town for the first time, you can't miss the Fantastic Museum, where Barnum & Bailey's "Olaf the Giant" comes to life. You can also find Bob Hope's stretch limousine, JFK's rocking chair, and signed sports memorabilia, like a pair of Shaquille O'Neal's shoes.

The Sisters Outdoor Quilt Show is one of the largest quilt festivals in the entire world, and has been a point of community pride for 50 years. The event is free to attend and brings in tens of thousands of visitors annually. Meanwhile, nature lovers can trek around Whychus Creek Trail, a 6.5-mile round-trip hike just south of town. For dining options in town, the Open Door offers wholesome food and fine wines in a warm, welcoming setting by the fire.

Burns

An isolated desert town with a few tourist spots, Burns is quite a spectacle in person. West of town, central Oregon's obsidian deposits can be found all over Glass Buttes across 6,000 acres of volcanic mountains and sagebrush. It is actually the largest obsidian deposit in the world and a popular destination for rock hounds, where personal mining is legal without a permit. The rock here is unique in that it is made up of a variety of types, including red fire and some with hints of gold, silver, and rainbow colors.

In town, the Harney County Historical Museum hosts artifacts and displays about its cattle ranching history and the lumber industry. At the museum, you can explore treasure troves of memorabilia, from old saddles and farm equipment to military relics and Native American tools. At Oards Gallery & Museum, you can explore more Native American pottery and art representing nine tribes from the region. If you crave something hot and hearty, try out The Pine Room, which offers generous portions and happy hour prices.

Pendleton

On the surface, Pendleton is a lovely small town in eastern Oregon. While that's certainly true, Pendleton Underground Tours offers a different perspective, taking visitors through historical passageways to secret Prohibition-era displays, such as a duck pin bowling alley, bordellos, card rooms, and even an opium den. Pendleton was once known as the entertainment capital of eastern Oregon, and after this engaging tour, it's clear to see why.

At the Tamastslikt Cultural Institute, learn about the influence of Oregon Trail pioneers and the vibrant cultures and legacies of the Cayuse, Umatilla, and Walla Walla peoples. Be sure to pay a visit to Alexander's Artisan Chocolates, an elegant chocolate factory and wine bar, for a truly winning combination. And no visit is complete without a stop at the Pendleton Hat Company for hand-made, signature fur felt hats to keep you feeling dapper long after you leave.

McMinnville

McMinnville is quite an underrated gem for tourists far and wide. If you’re looking to experience something delightfully strange during your time in town, check out the annual UFO Festival. This two-day celebration was inspired by the famous 1950 sighting, when residents captured photos of an alleged flying saucer that went on to become one of the most well-known sightings in UFO lore. Today, the festival honors that quirky piece of local history with a lively mix of costume parades, guest speakers, and cosmic-themed activities. You’ll encounter enthusiastic festivalgoers decked out in their best extraterrestrial attire, all joining in on the fun of this charming and truly otherworldly community tradition.

Meanwhile, the Evergreen Aviation & Space Museum is renowned for its extensive collection of innovative flight exhibits and rich pilot history. With more than 150 displays, including aviation exhibits in the West Museum Pavilion and impressive space exploration galleries in the East Museum Pavilion, this landmark is a standout destination for travelers. This town also loves its wines, and locales like Coeur De Terre Vineyard feature organically farmed wines and tasting rooms in the foothills of the Oregon Coast Range. Galen McBee Airport Park is another quirky stop just adjacent to McMinnville Municipal Airport, with walking trails that cross woodland picnic spots, whimsical mushroom houses, and forest streams.

Travelers who appreciate unusual charm will find plenty to enjoy in places such as Boring and Sisters, where creative attractions and local stories shape the rhythm of daily life. Each town offers its own brand of eccentricity, inviting visitors to explore, discover, and enjoy moments that feel unexpected. These Oregon communities prove that small towns can be wonderfully distinctive and full of character.