Nebraska

American backroads travelers often spend inordinate amounts of time looking for off-the-beaten-path treasures in old-time diners, vintage service stations, kitschy theme parks, and mom-and-pop gift shops. They simply search for what makes them happy.

Imagine: you step off a train in a small French town. The station doesn’t have internet access and you don’t have a place to stay. As the sun begins to set, you’re forced to walk down the cobbled streets, hoping a tattered-looking hotel spotted in the distance will have a bed for you.

For globetrotters like Catherine Sypal, this type of open-ended adventure with no guarantees is the appeal of traveling alone.

Sypal...