One designated road at a time, with the guides we publish along it. We list the stops; how far you go in a day is yours to decide.
Highway Heads road trips
Trips
Every trip
The Great River Road
The road that follows the Mississippi from the headwaters in northern Minnesota down to the Gulf, through ten states and, as the Federal Highway Administration puts it, hundreds of river towns.
9 guides
The Historic National Road
The first road the federal government ever paid to build, running west from Maryland to Vandalia, Illinois. The Federal Highway Administration calls what survives along it a physical timeline: inns, tollhouses, diners and motels.
4 guides
Historic Route 66
The Mother Road. The Federal Highway Administration’s designated byway runs 1,409 miles across six states; our guides on it run from Chicago as far west as Flagstaff.
8 guides
Journey Through Hallowed Ground
One hundred and eighty federally designated miles from Gettysburg down to Monticello, through ground the Revolutionary War, the Underground Railroad and the Civil War each crossed.
4 guides
The Lincoln Highway Across Nebraska
Four hundred and fifty designated miles of the Lincoln Highway, running west across Nebraska along the Platte.
3 guides
The Natchez Trace Parkway
A 444-mile federal parkway running from Natchez up to Nashville, built along the historic overland route between the two.
4 guides