This is a big year for America. The country turns 250 years old in 2026 and its favorite road, historic Route 66, is turning 100. That means a whole century of memories for amazing family travel road trips from Chicago to California and back.
The route’s official start is in Chicago, where it then travels through eight different states before ending on the Pacific Coast in the beach city of Santa Monica. This beach town isn’t just the end of the road (there’s actually a Santa Monica 66 End of the Trail sign marking the end of the route, the perfect place for a photo finish), it’s also quintessential California. The surf vibe is in full swing, there is plenty to see and do, and the sun is shining almost every day.
You’ll want your road trip to culminate with a trip to Santa Monica Pier, where you can enjoy some souvenir shopping and plenty of good eats, along with carnival games and rides on the waterfront — the 1939 carousel is a nostalgic ride you won’t want to miss. Take a walk along the boardwalk, dip your toes in the sand or build sandcastles with the kids at Santa Monica State Beach — and, of course, watch surfers catch some waves while you’re there.
Just a short walk from the pier is Third Street Promenade, a pedestrian-only outdoor shopping area filled with popular chains and charming boutiques, along with plenty of places to grab a refreshing drink or a bite to eat.
There are plenty of options in the city when it comes to accommodations, from 5-star Shutters on the Beach to the affordable Days Inn by Wyndham Santa Monica. But one of the best things about Route 66 ending in Santa Monica is it drops you off in the perfect location to experience all the rest of what Southern California offers, like Malibu, Huntington Beach and Hollywood. Even San Diego and Santa Barbara are just a few hours’ drive away.
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