It’s a big year for travel in terms of destinations highlighting a number of milestones: America’s 250th, Colorado’s 150th and Route 66’s 100th.  

Maybe it started with visions of driving my dad’s 1969 GTO down at least a portion of Route 66, or maybe it’s my general obsession with the decade of flappers, but when I heard about Route 66’s anniversary, I started planning — long before many of the key-city players listed celebratory events.  

Having grown up in Chicago, I’ve already explored the beginning of the Mother Road  — though I’m hoping to return this year. And although I’ve been to Santa Monica, I had to revisit it in 2026 as a tribute to Route 66. 

I’ve always joked with my California-native husband about how California seems, let’s just say, a little more carefree when it comes to lasting commitments  —  the opposite of my loyal, Midwestern-rooted family. Take, for instance, California’s approach to naming the official endpoint of Route 66.  

While Chicago has always maintained its claim to the place Route 66 begins, the famous road’s ending point in California has shifted fairly significantly throughout history.  

It originally officially ended at the intersection of 7th Street and Broadway in Los Angeles, but in 1936, the route extended 13 miles west into Santa Monica to connect with Route 101 and the Pacific Coast Highway. In 1964, they somehow shortened the route, naming Pasadena as the Mother Road’s formal ending.  

As if that wasn’t enough change, Route 66 was once again truncated in Needles. These days, Santa Monica Pier has reasserted its station as the official end of Route 66, with numerous signs. Though I wanted to hit every historic end-point of Route 66 in California, logistics of dealing with traffic in L.A. at 5 p.m. on a Friday and time involved driving to Needles led us to focus on the Pasadena and Santa Monica endings. 

If you like the idea of Aspen’s carnival games and rides that are coming this Fourth of July weekend to Rio Grande Park (complete with a 65-foot Ferris Wheel and carousel), then you’ll love Santa Monica Pier’s permanent amusement park. An unlimited-ride wristband is just $45 — $35 for kids 7 and under — and includes all kinds of rides, like the Pacific Plunge, the Shark Frenzy Tilt-a-Whirl, a Scrambler and a roller coaster. It features a 130-foot high Ferris Wheel, which happens to be the world’s first and only solar-powered wheel, complete with 174,000 LED lights displaying custom animations. 

While plenty of fine dining establishments exist in Santa Monica, from Michelin-starred restaurants to classic steakhouses and seafood, if you want a quick bite at the last place to grab a burger on land, Pier Burger offers a fresh ono burger for under $12. 

Speaking of burgers, remember when Aspen had a McDonald’s? Well, if you care to visit the original McDonald’s, which Dick and Mac McDonald opened in 1937 in Monrovia, Calif., and then moved to San Bernadino in 1940, it’s part of the Route 66 tour.  

The original McDonald’s emblem at the museum.Kimberly Nicoletti/Courtesy photo

They focused on their “speedy service system” as McDonald Hamburgers in 1948, and the building still stands, hosting a free museum showcasing all things big and small related to the now-huge franchise (in 1955, Ray Kroc visited the brothers and convinced them to let him franchise the fast-food joint). Outdoor mascot statues and Play Place relics offer plenty of fun photo opps, and you can spend a lot of time studying all the tiny toys that span various countries indoors. Colorful murals on the building highlight Route 66 history. 

Puttering down the streets of Route 66 from San Bernadino to Santa Monica will take hours upon hours, so I recommend stopping at the Wigwam Motel Village in Rialto/San Bernadino after the McDonald’s museum, and then hopping back on the highway to Pasadena. The Wigwam Motel is a classic; it’s one of only three remaining Wigwam motels of the original seven, and the old cars make for great photos. A gift shop offers all kinds of Route 66 souvenirs. 

The Wigwam Motel on California’s Route 66.Kimberly Nicoletti/Courtesy photo

One of Pasadena’s Route 66 claims-to-fame comes in the form of the Saga Motor Hotel. Architect Harold Zook designed the mid-century hotel to catch motorists’ eyes, complete with a neon sign in Moorish-inspired script and adorned concrete blocks. It has been featured in television series, commercials and films, including Apple TV’s “Palm Royale,” ABC’s “Fresh Off the Boat” and Showtime’s “Ray Donovan.”  

On June 22, Aspen Ideas: Health featured Ezekiel Emanuel, author of “Eat Your Ice Cream: Six Simple Rules for a Long and Healthy Life” who talked about longevity habits. Of course, indulging in ice cream followed. That said, if you’re a fan of old-time ice cream shops, plan a stop at The Fair Oaks Pharmacy and Soda Fountain on Route 66, just outside of Pasadena (across from another historic Route 66 restaurant, Gus’s BBQ). 

Even if you don’t order a softball-size ice-cream scoop, all of the memorabilia makes it worth the jaunt. It’s been serving sweets since 1915 and features plenty of old-time candy, from retro-wrapped Hershey’s bars to Pop Rocks and more. Don’t miss the adjoining room, stocked full of games and other goodies organized by decade. For example, in the 1960’s section, you’ll find everything from 60sOPOLY to high-wheel robot toys, Fly’s Eyes, lava lamps and TEEN magazine. 

My dog, Hani, on the Snoopy star.Kimberly Nicoletti/Courtesy photo

Finally, the route to Santa Monica provides plenty of boutiques on Sunset Boulevard, as well as legendary rock ‘n’ roll bars like The Rainbow Bar & Grill and Whisky a Go Go (prepare to stand in line to see a band) and, of course, the Hollywood Walk of Fame.  

Happy historic travels! 

Kimberly Nicoletti is a freelance writer and editor whose trips usually revolve around anywhere she can take her terrier-mix rescue.