These weird, wild, and wonky detours are worth pulling over for.
In a state with a well-publicized reputation for eccentricity plus thousands of miles of highways crisscrossing it, you’re almost guaranteed to encounter some Americana oddities along the way. And Oregon does not disappoint, with hand-built theme parks, niche museums, real-life ghost towns, a shipwreck you can walk up to at low tide, and even Howard Hughes’s “flying boat.” Route your road trip to hit at least a few of these classic roadside attractions.
WHERE: Port Orford
Don’t be alarmed if you spy a brontosaurus peeking out of the evergreen forests along Highway 101, just south of Port Orford on the southern Oregon Coast. Built in the 1950s by an amateur paleontologist, who traveled the world studying fossils in museums and archives, Prehistoric Gardens looks like a real-life Jurassic Park, except the 23 dinosaurs inhabiting this temperate rain forest are—thankfully—life-size sculptures.
Shaniko Ghost Town
Oregon’s many ghost towns captivate the imaginations of road-trippers and photographers with the mysteries of who might’ve called these frontier communities home. Shaniko in central Oregon is a picture-perfect example, with a decaying hotel, jail, and schoolhouse among the still-standing structures. Considered the “Wool Capital of the World” at the turn of the century, the town peaked at nearly 500 residents; today Shaniko looks like the abandoned set of a Wild West film.
The Freakybuttrue Peculiarium
A truly peculiar roadside attraction found in Portland’s Inner Southeast, the Freakybuttrue Peculiarium looks like a do-it-yourself Ripley’s Believe It or Not! museum. It’s the brainchild of several local artists, who fill the gallery and adjoining shop with a menagerie of macabre art and oddball kitsch. Popular photo ops include the stick-your-head-in alien autopsy exhibit and selfies with the giant Bigfoot statue.
Oregon State Hospital Museum of Mental Health
Visit a former insane asylum in Salem that served as the primary set for the legendary 1975 classic One Flew Over the Cuckoo’s Nest, starring Jack Nicholson. In the late-19th-century facility, volunteers operate the nonprofit Oregon State Hospital Museum of Mental Health, which explores the somber history of psychiatry through artifacts such as straitjackets sewn by patients and now-regrettable treatment devices. A popular permanent exhibit is dedicated to the Academy Award-winning film.
Take a literal walk down Storybook Lane in this old-school theme park to see scenes from popular fairy tales and nursery rhymes brought to life, including folk art–inspired statues of characters such as Little Red Riding Hood and the Seven Dwarfs. It’s all the handiwork of one eccentric man: Roger Tofte, who, in true Oregon fashion, self-funded the park and built nearly all the attractions himself. Enchanted Forest has remained a Willamette Valley fixture along I-5 since opening in the 1970s.
The Oregon Vortex and House of Mystery
WHERE: Gold Hill
In southern Oregon between Grants Pass and Medford, there’s a place that seems to defy all the laws of physics—where a ball rolls uphill and a person’s height appears to change as they move. Optical illusion or some strange paranormal activity? That question has made The Oregon Vortex and House of Mystery a popular diversion since the 1930s.
Peter Iredale Shipwreck
When the tide is low on the beach at Fort Stevens State Park, you can stroll up to the ghostly remains of the Peter Iredale, a four-masted steel ship that ran ashore here in 1906. It’s the most accessible of the thousands of vessels that have wrecked along the Oregon Coast, earning it a rather foreboding nickname: “the Graveyard of the Pacific.”
Paul Bunyan Statue
Statues of this mythical logger are common roadside sights in the American West, though North Portland’s 31-foot-tall Paul Bunyan smiles confidently as the king among them. The unmissable sculpture went up in 1959 to mark the 100th anniversary of Oregon’s statehood. Neighbors have kept Bunyan in good shape over the years, with periodic renovations and fresh paint—that likely explains his perennially pearly concrete smile.