Start your day with breakfast at Russell’s, a beloved Pasadena spot since 1930. Drive along Colorado Boulevard, following the Tournament of Roses Parade route, and visit The Original Whistle Stop, a classic train hobby store. Continue to Monrovia to admire the Aztec Hotel’s unique Mayan Revival architecture. Next, follow Historic Route 66 to The Donut Man in Glendora, a Route 66 favorite since the 1970s. Before leaving Los Angeles County, explore the shops and restaurants in Historic Downtown Claremont. As you head east, Foothill Boulevard will lead you to Upland, where you can see retro Route 66 streetlamps and the “Madonna of the Trail” statue. In Rancho Cucamonga, stop by the historic Sycamore Inn, a local institution since the mid-1800s and a Route 66 favorite, known for its steakhouse. After visiting the Sycamore Inn in Rancho Cucamonga, head to the nearby Cucamonga Service Station, now a mini-museum showcasing photos and memorabilia. Continue along Historic Route 66 on Foothill Boulevard to San Bernardino, where you can explore the Original McDonald’s Site & Museum. For dinner, enjoy delicious Mexican cuisine at Mitla Café. End your day by checking into the Wigwam Motel, known for its teepee-shaped accommodations and modern amenities, including a swimming pool to unwind before settling in for the night.