On the Road
Carey's Cross-Country Road Trip
Santa Monica → Chicago → Northern Loop → San Marino
July 23 – August 10, 2026 · ~5,569 miles
Keep driving. Keep noticing.
The route
Twenty-four stops. Santa Monica to San Marino.
From the Pacific across deserts and plains to Chicago, then north through the Badlands, Mount Rushmore, Custer State Park, Devil's Tower, and Yellowstone, west through Idaho and Oregon, and down Highway 1 via Big Sur with a final overnight in Cambria before the last inland run to San Marino.
From the road
City by city
Start with the overview, then scroll into each city's full strip. Tap a city to jump there; tap a thumbnail to enlarge.
The payoff
Chicago interlude
Two full days (and more) in the Windy City — the design goal of the long desert days.
From the same planning arc
Side trips & alternates
Related guides planned alongside the main loop — Baja weekends and a Highway 1 + Jackson Hole variant.
Keepsake
Trip summary
Total approximate driving distance: 5,569 miles
Start: Santa Monica, California — July 22/23, 2026
Furthest point: Chicago, Illinois (late July)
Northernmost: Green Bay / Minneapolis / Yellowstone region
Finish: San Marino, California via Cambria (Highway 1 / Big Sur en route) — August 9–10, 2026
You crossed deserts, plains, the Midwest, the Badlands, Mount Rushmore, Custer State Park, Devil's Tower, Yellowstone, the Pacific Northwest, and the California coast. Hotels ranged from Hyatt Regency Tulsa and the Tiger Hotel in Columbia to the Irma in Cody and The Aspen in West Yellowstone. Nights included concerts in Bend, rodeos in Cody, river walks in Chicago, and late drives through vineyards and mountains.
— End of the Road (for now) —