The Weirdest and Most Wonderful Roadside Attractions on Route 66

From wild to straight wacky, America's quintessential roadtrip has got a little something for everyone.Just like the first pancake in a batch, America’s first paved transcontinental road, Route 66, is unique and a little bit quirky. Stretching 2,448 miles from Chicago, Illinois, to Santa Monica, California, the “Mother Road” was commissioned in 1926 and finished in 1938—a time of expansion, when Midwesterners moved west for jobs, and the post-WWII economic boom spurred the popularity of the great American road trip. Route 66 is a time capsule of this history, full of classic diners, two-car gas stations, and lots of neon-covered signs. While there are big cities and iconic monuments spread across the highway, much of its Americana magic lies in the unexpected roadside finds. If you’re planning a road trip this year to mark the highway’s 100th anniversary, these are the weirdest (and thus most wonderful) destinations to visit along Route 66. Following Route 66 from Chicago will lead you to…well, a lot of brick. Aptly named the Historic Brick Road, this stop will give you a unique peek into pre-Route 66 history. It was only technically part of Route 66 from 1926 to 1930, after which it was decided to shift Route 66 just ever so slightly east. In 1931, the 1.4-mile road was restored with hand-laid brick over the existing concrete, earning the Historic Brick Road a place on the National Register of Historic Places for its excellence in brick road construction—so good, in fact, that you can still drive across it today.So, no, the Historic Brick Road wasn’t made of brick during its brief stint as part of the Mother Road, but it’s still a work of genius. It’s not a stop that requires a lot of time, so it’s easy to tack onto your... EXPLORE THE WORLD LIKE A LOCAL Unlock exclusive content, tools and guides for your next unforgettable adventure. Members-only insider content Unlimited access to Fodor's AI assitant Instant, free e-Guidebook Unlimited AI Exclusive Content Early Access Everything included in the monthly version. A free e-guidebook as a gift (valued up to $26.99) each year.