Route 66 didn’t just connect Chicago to Santa Monica, it helped create an entirely new kind of American travel culture. When the highway was officially established in 1926, it quickly became a major corridor for migration, trade, and long-distance driving. But it wasn’t until the post-World War II boom in automobile ownership and family vacations that Route 66 truly transformed. As more Americans took to the road for leisure, small towns suddenly had a new challenge: How do you get travelers to stop? The answer was creativity, visibility, and competition. Entrepreneurs along the highway began building eye-catching stops right along the roadside: motels with glowing neon signs, oversized statues, and oddities designed to grab attention as drivers sped by. These weren’t random curiosities, they were survival strategies for businesses. A giant muffler man, a world’s-largest anything, or a themed motel was advertising meant to turn a passing car into a paying customer. Over time, these stops evolved into what people now casually call “tourist traps,” though that term misses part of the story. They were often deeply local, reflecting regional identity, humor, and pride. A fiberglass dinosaur in the desert or a kitschy motor court in Oklahoma was about giving travelers a memory they couldn’t get anywhere else. Route 66 became an open-air museum of American imagination, where each town tried to outdo the next with something bigger, brighter, or stranger. Even after the construction of the Interstate Highway System pulled traffic away from the Mother Road, many of these attractions survived. Some faded, others were restored, and many became historic landmarks in their own right. Today, they’re central to Route 66’s identity, enduring symbols of a time when the journey itself was the destination and stopping along the road was part of the adventure. This year marks Route 66’s 100th Anniversary, so to celebrate, here are more than 100 of the best roadside attractions along the route. Lou Mitchell’s is a legendary eatery in downtown Chicago. ILLINOIS Route 66 Begin Sign (Chicago, IL)The symbolic starting point of Route 66. Most travelers stop here for the classic “begin” photo before heading west. Lou Mitchell’s (Chicago, IL)A legendary breakfast stop that has fueled Route 66 travelers since the highway’s early days, known for its welcoming vibe and old-school charm. Willis Tower (Chicago, IL) A quick urban detour before leaving the city—one of the tallest skyscrapers in… [TheTopNews] Read More.
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