Oregon is a magnet for road trippers drawn to its natural wonder, but it’s also one of America’s quirkiest states when it comes to weird roadside attractions. Whether you’re chasing the old-school oddities, outsider art, or nature gone strange, these ten stops will make your Oregon adventure truly unforgettable.
1. Prehistoric Gardens (Port Orford)
Along Highway 101, this Jurassic-era park nestles life-sized, rainbow-painted concrete dinosaurs among the redwoods. Built in the 1950s, it’s petrified kitsch and childhood wonder all at once, with creature scenes waiting for photos around every bend.
2. Harvey the Rabbit (Aloha)
Towering over the roadside in Aloha is Harvey, a giant fiberglass rabbit with a storied history. Repaired from a Texaco “Big Friend,” he became a local landmark and brings luck to those who wave on their way by.
3. Dog Bowl (Portland)
For dog lovers and art fans, Portland’s North Park Blocks are home to an oversized bronze dog bowl on a checkerboard tile “kitchen floor.” Installed as public art, it’s a beloved local quirk and a real drinking fountain for fou-legged friends.
4. Bigfoot Says “Hold My Beer” (Crescent)
Crescent’s Bigfoot Tavern features a hulking wooden sasquatch statue cheerily hoisting a beer. It’s the ultimate ‘weird west’ selfie—plus, Bigfoot’s neighbors include carvings of oversized bears and quirky roadside décor.
5. Short Bridge Ghost Towne (Foster)
Not a true ghost town, this whimsical Highway 20 roadside stop is a false-front town, complete with “Slim’s Café” and “Drunken Horse Saloon.” Great for photos and sure to delight kids and the young at heart.
6. Pulpit Rock (The Dalles)
In the heart of a residential street stands Pulpit Rock, a monolith once used for sermons by 19th-century missionaries. Instead of uprooting it, The Dalles chose to preserve the past—now it juts up, encircled by modern homes.
7. Oregon Caveman (Grants Pass)
This stooping fiberglass caveman has guarded the entrance to Grants Pass since 1971. He’s a throwback mascot who’s survived arson, vandalism, and decades of amused tourists—a right of passage photo-op for passing travelers.
8. Smiley Face of Trees (US-18, Near Willamina)
From the highway near Willamina, look up: a hillside is planted with Douglas fir and larch trees that, in autumn, form a beaming smiley face visible from the road. A cheerful “hello” sculpted right into the Oregon landscape.
9. The Troll Bridge (Portland)
Hidden beneath a train trestle on McNamee Road, a growing community of troll dolls have taken up residence, nailed in place by fans. Everyone is welcome to add a troll to the thriving bridge-side colony—it’s as weird as it sounds.
10. The Octopus Tree (Cape Meares)
Located on the coast, this massive Sitka spruce has naturally grown into a wild, multi-limbed “octopus” shape. Estimated to be over 250 years old, it’s a natural oddity that’s puzzled and amazed generations of visitors.
From fiberglass giants and tree-formed emojis to psychedelic dinosaurs and bridges of trolls, Oregon’s roadside wonders are irresistible pauses on any road trip. Each tells a story—sometimes mysterious, sometimes silly, always unforgettable—proving that the path through Oregon is as magical as the destination itself.
Sources
[1] https://www.pdxmonthly.com/travel-and-outdoors/oregon-oddities-roadside-attractions
[2] https://thatoregonlife.com/2021/09/weirdest-roadside-sights-oregon/
[3] https://www.businessinsider.com/things-to-see-on-a-road-trip-2017-6
[4] https://www.reddit.com/r/oregon/comments/1cgekut/top_weird_touristy_things_to_do/
[5] https://www.atlasobscura.com/things-to-do/oregon
