10 Best: Funny Sites Along Route 66

  • Historic Route 66

    Journey Down Route 66, America's Main Street

    Route 66 was established in 1926, making it one of the oldest highways in the United States. The road originally stretched 2,451 miles from Chicago all the way to the coast of Los Angeles, This historic stretch of blacktop is perhaps best known for its kitschy roadside attractions – perfect stops for family photo ops or a picnic lunch.

    Photo courtesy of Sam Howzit

  • Catoosa Blue Whale

    Swimming with the Catoosa Blue Whale in Catoosa, Oklahoma

    If you could go back in time and drive Route 66 through Oklahoma in the 1970s, you'd notice a roadside swimming hole teeming with people and one really big, smiling blue whale. Hugh Davis built the whale in 1970 to give his kids something to jump off of into the water. While it's closed to swimmers now, you can still stop in for a photograph of the Catoosa Blue Whale, maintained by the local community.

    Photo courtesy of openroads.com

  • Totem Pole Park

    Picnic at Totem Pole Park

    Elsewhere in Oklahoma, just over 3 miles off the Mother Road, sits Totem Pole Park. The work of local folk artist Ed Galloway, the park features a 90-foot tall totem pole built on the back of a cement turtle, as well as ten other totems spread throughout the 14-acre park.

    Photo courtesy of Kevin

  • Polk-a-Dot Drive In

    Grab a Bite at the Polk-a-Dot Drive In

    The only thing as American as Route 66 is a drive-in. Near the start of Route 66 in Braidwood, Illinois, you'll find the 50s-style drive-in dinner known as the Polk-a-Dot. Pull up for a burger, fries and shake alongside the likenesses of Marilyn Monroe, James Dean and Betty Boop.

    Photo courtesy of Anne Hornyak

  • Cadillac Ranch

    Pay Your Respects at Cadillac Ranch

    Set amid the flat expanse of the Texas panhandle, just west of Amarillo on Route 66, is a bizarre tribute to classic cars: Cadillac Ranch. A San Francisco art commune called the Ant Farm installed the 10 Cadillacs nose first in the dirt. Should you stop in for a look, bring a can of spray paint and add your own touch to this iconic North Texas monument.

    Photo courtesy of longhorndave

  • Ostriches look cute but are unpredictable

    Here's Lookin' at Ya

    Somewhere between Albuquerque and Flagstaff sits a rock store with an adjacent ostrich petting farm.  It's tempting to want to feed or pet these funny creatures, but believe us, it's not a good idea.  Ostriches can do damage when they're agitated.  

    Photo courtesy of Tambako the Jaguar

  • The Rusty Bolt

    Swing By the Rusty Bolt for Souvenirs

    Every vacation needs a few souvenirs, and after you finish your meal at Roadkill, you can pick up your Route 66 memorabilia at the Rusty Bolt. The store's interior is packed with everything kitschy Americana with an entire room dedicated to biker gear. The shop's exterior, however, is the real draw. Classic cars and strange mannequins make the Rusty Bolt a very popular leg-stretching stop.

    Photo courtesy of Ronnie Macdonald

  • Jackass Junction

    Jackass Junction - It's Not What You Think

    As Route 66 passes through Arizona, you'll stumble upon the living ghost town of Oatman, with a year round population of only 100 or so people. During Oatman's gold rush in the early 1900s, the town became a popular trading post with plenty of burros brought by the miners. They were eventually set free, and the wild burros still roam the streets today. You can even purchase burro pellets in the shops to feed the local "wildlife."

    Photo courtesy of Alon Banks

  • Wigwam Village Motel

    Rest Your Head at the Wigwam Village Motel

    When you're ready to rest your head for the night, there's nothing that says Route 66 quite as much as the Wigwam Village Motel 6 in Holbrook, Arizona. Accommodations are in fact teepees as opposed to wigwams, but they're delightfully kitschy nonetheless. Should you be lucky enough to stay in Wigwam #1, you'll be breathing the same air as Oprah and Gayle, who stayed as part of the TV show Oprah and Gayle's Big Adventure.

    Photo courtesy of Chuck Coker

  • Amboy Shoe Tree

    Lighten Your Load at the Amboy Shoe Tree

    You've made it all the way to California, and now it's time to lighten your load a little. As you drive toward the town of Amboy, you'll notice a tree with some rather odd decorations. Aside from being the only tree in sight, the tamarask tree by the side of the road is covered in the shoes of hundreds of travelers. Make sure to leave your own adornment before reaching the end of the road.

    Photo courtesy of Chuck Coker

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