route 66

Route 66

Indisputably the most iconic—and historic—U.S. drive, the 2,400-mile stretch of road runs between Los Angeles and Chicago, and passes through eight states: California, Arizona, New Mexico, Texas, Oklahoma, Kansas, Missouri, and Illinois. The roadway was flooded with hopeful families in the wake of the infamous Dust Bowl, which displaced countless numbers of people that flocked to California in search of employment. Today, though not a main route, it remains a favorite drive for road trippers. It is, after all, where the concept of road tripping was born. Some highlights along the way:

  • Cadillac Ranch in Amarillo, TX: Sort of a mash-up of art and automobiles, this installation is a collection of graffiti’ed Cadillacs jutting out from the ground.
  • Blue Whale of Catoosa, OK: It’s literally just a giant blue whale on the side of the pond and has been drawing in crowds since its construction in 1972. Tourists stop by to picnic and, of course, to pose for photos with the sculpture.
  • Roy’s Motel & Café, Amboy, CA: A fixture on the route since 1938, the hotel is undergoing restoration with plans to reopen for the first time since 2005.
  • End of the Trail, Santa Monica, CA: The very end of Route 66 takes you to a classic Oceanside boardwalk. You’ll find lots of junk food, games, and, of course, stunning ocean views.

great river road

The Great River Road

Take a modern trek down the “Ol’ Mississip” on this 2,000 mile collection of roads—not a single one, despite the name—that pass through ten states: Arkansas, Illinois, Iowa, Louisiana, Mississippi, Missouri, Tennessee, and Wisconsin. Along the way you pass farms, meadows, swamps, forests, and seemingly countless numbers of casinos. (Of course, you’ll also pass a good portion of industrial eyesores. But the good outweighs the bad.) The most popular attractions are the plethora of historic plantations that you can tour, all of which are in Louisiana. There’s Magnolia Mound in Baton Rouge; Laura: A Creole Plantation in Vacherie; Rosedown Plantation in St. Francisville; and Nottoway Plantation in White Castle, among others. Also worth checking out:

  •  Alton Museum of History and Art, Alton, IL: Intended to showcase the history of the area, the museum features exhibits about the Civil War, Lincoln/Douglas Congressional Debates of 1858, and even Robert Pershing Wadlow, a former resident who, at 8’11” is the tallest person ever to live.
  • Pere Marquette State Park, Grafton, IL: The sprawling 8,050-acre park is the largest in the state and offers stunning views and an array of activities, from biking to horseback riding and even overnight camping.
  • Daniel Boone Home, Defiance, MO: The house, built by the infamous pioneer’s son in 1803, is where Boone spent his final days before dying in 1820.