9. Highway 41 from Miami to Lake Superior
Once early highway addicts did Miami to Maine, Miami to Michigan became the next north-south challenge to conquer. Crossing Florida’s Everglades, Highway 41 veered north and careened between rural solitude -- think Gibsonton, a small Florida town founded by carnival workers -- and big cities like Tampa, Atlanta, and Nashville. The construction of Highway 41 spurred a border war between Kentucky and Indiana where the road crosses the Ohio River into Evansville, although no fights have been documented since 1926 over the following 282 miles of Hoosier State emptiness. That abruptly ended, however, for early drivers entering bustling Chicago, where Highway 41 (or Lake Shore Drive) was a main thoroughfare through the city’s most scenic sections -- and home to the vaunted Soldier Field.
North of the metropolis, Highway 41 was the earliest “vacationer’s route,” with legions of American families riding the newfound freedom of the automobile north to Lake Michigan, Lake Winnebago, and Michigan’s idyllic Upper Peninsula, most of which has maintained the rustic charm it had in the mid-20th century.
10. The CanAm Highway (US Route 85)
While the 19,000-mile PanAm Highway took nearly a century to come to fruition, the CanAm Highway was completed in 1926, Year Zero for America’s best cross-country roads. US Route 85 took early drivers north from the Mexican border outside El Paso, ascending slowly (good for those early, not-so-reliable cars) through New Mexico cities Las Cruces, Albuquerque, and Santa Fe before skirting the regal Rocky Mountain range through Pueblo, Colorado Springs, and Denver. North of Cheyenne, the CanAm got progressively more tough to navigate, though, as early adventurers got a look at South Dakota’s Black Hills, with an eastward jog through once-rough-and-tumble Wild West ghost towns like Deadwood and Spearfish. After that, nothing but beautiful scenery stood in the way of the Canadian border, including a pass-by of North Dakota’s highest points, White Butte and Black Butte, and a drive through the spectacular Badlands. Surely the extraterrestrial terrain there was something no early 20th-century traveler had ever seen before the advent of the automobile.