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.
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.
From the road
Loose Videos
Every clip from the trip, gathered by location. Tap a location to jump there; tap a clip to play.
The payoff
Chicago interlude
Two full days (and more) in the Windy City — the design goal of the long desert days.
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) —