Get your kicks on America's original road trip—this 2,448-mile journey from Chicago to Santa Monica is a trip down memory lane of our nation's history. Our editors and experts handpick every product ...

Driving the entirety of Route 66 is no easy task. It takes months to plan and weeks to execute. Why exactly does a person need to set aside so much time for Route 66? The answer lies not in the road ...

Our Route 66 road trip ended at the beginning, at East Jackson Boulevard and South Michigan Avenue in Chicago, where a brown sign hanging 12 feet high on a light post tells people they’ve reached the ...

Samantha explores Route 66 sites from St. Louis to Tulsa. Samantha starts her trip with a view of the St. Louis Arch and visits Ted Drewes Frozen Custard, famous for its thick desserts. She meets ...