Amarillo, Texas
This public art installation by avant-garde group Ant Farm has stood in rural Texas since 1974. Originally a commentary on the rise and fall of the famous tailfin automobile style, the cars are now routinely painted over with layers and layers of graffiti. Even though it is located on private land, visitors are actively encouraged to stop and explore.
Chelsea, Oklahoma
Featuring quirky designs and the world's largest concrete totem pole, Ed Galloway's Totem Pole Park remains one of Oklahoma's oldest and largest displays of folk art. Also on the property is the Fiddle House, further underscoring Mr. Galloway's skill and love of woodworking by displaying his handmade fiddles.
Oro Grande, California
With over 200 bottle trees, it's easy to get lost in this sparkling forest of glass. Elmer himself leads tours around the grounds while giving the backstory on his collection and future work. Interspersed among the trees, and adding to the decor, are rusted cars, boats, metal signage, and even an old missile!
Catoosa, Oklahoma
A trip along Route 66 isn't complete without a stop at the world-famous Blue Whale of Catoosa. Constructed as an anniversary gift for the builder's wife, the whale has become a favorite summer attraction for residents and visitors who use the tail as a diving board for the swimming pond in which the whale is built.
Arcadia, Oklahoma
Built in 1898 by William H. Odor, this architectural oddity served a dual purpose for many years: traditional livestock housing on the ground floor and a community meeting place on the second level. After more than 100 years, The Arcadia Round Barn remains one of, if not the only, truly round barn in the United States, as most are either rectangular, hexagonal, or octagonal.
Holbrook, Arizona
Though it may be called the Wigwam Hotel, each bungalow is actually built in the style of a tipi. In keeping with it's "blast-from-the-past" theme, classic cars are parked across the parking lot. Don't expect online reservations, however. The only way to book a room is by calling the office on their...gasp...landline.
Wilmington, Illinois
As the original billboards of the 1960s, "Muffler Men" were large roadside monuments that promoted businesses, typically with whatever they held in their arms. As one of the last of his kind, the Gemini Giant still stands (at 30 feet tall) alongside the Launching Pad Drive-In, greeting all visitors to the town of Wilmington.
St. James, Missouri
You never knew vacuums were so important to everyday life. After one visit to the Vacuum Museum and Factory Outlet, curator Tom Gasko will have you thinking differently. These quirky tours will show you everything from the "modern" vacuums of the 1950s to the futuristic robots that clean our homes today.
Galena, Kansas
Of the entire 2,451-mile length of Route 66, only 13 miles actually passed through Kansas. But that doesn't mean there isn't anything of note in the Sunflower State. While doing research for their film Cars, a Pixar team took inspiration from a former Kan-O-Tex service station in Galena. The stop's 1951 boom truck inspired the beloved character Tow Mater.
Tucumcari, New Mexico
The Route 66 Monument may be among the newest attractions along the famous highway, but its inspiration derives from the classic cars that drove across the country during the 50s and 60s. This oversized tailfin sculpture proclaims the routes name in a stylized text and points the way westward to the Santa Monica terminus.
