The Huck Finn
Kick off the journey at Lake Itasca and wash up at the Gulf of Mexico, figuring on 36 hours of driving time. If a long weekend sounds less intimidating, just follow the Great River Road to the end of the Little Dixie Highway in Clarksville, Mo. The byway is blissfully well-marked: Look for signs bearing the green pilot’s wheel to guide you down the river.
Where to stop
Prairie du Chien, Wis.
Harpers Ferry, Iowa
Ste. Genevieve, Mo.
Trail of Tears State Park, Mo.
“Old Man River,” Paul Robeson
“Big River,” Johnny Cash
“Mississippi River,” Muddy Waters
“Proud Mary,” Ike & Tina Turner
“Walking to New Orleans,” Fats Domino
“Crescent City,” Lucinda Williams
From Chicago’s Lakeshore Drive to the Santa Monica pier, figure on eight or nine days. If you want to cheat, hop on Interstate 35 to Kansas City and join up with Route 66 in Baxter Springs, Kan.
Where to sleep
Best Western Rail Haven, Springfield, Mo.
Campbell Hotel, Tulsa, Okla.
The Big Texan, Amarillo, Texas
Blue Swallow Motel, Tucumcari, N.M.
El Rey Inn, Santa Fe, N.M.
Hotel Andaluz, Albuquerque, N.M.
La Posada, Winslow, Ariz.
Hotel Monte Vista, Flagstaff, Ariz.
Wigwam Motel, San Bernardino, Calif.
“(Get Your Kicks On) Route 66,” Chuck Berry
“Going to California,” Led Zeppelin
“California Love,” 2Pac
“California Dreaming,” The Mamas & the Papas
“West Coast,” Lana Del Rey
“Paradise City,” Guns N’ Roses
Dakota or Bust
It’s perfect for a long weekend, but you can easily stretch this trip into a whole week if you linger at historic sites and recreation areas. The most remote point of the drive, Devil’s Tower, is a 12- or 13-hour drive from Minneapolis. Heading west on Interstate 90 from Sioux Falls, S.D., don’t miss Exit 131 for the Badlands Scenic Byway, a stunning highlight of the drive west.
Where to sleep
The Jasper Stone Bed and Breakfast, Sioux Falls, S.D.
Cedar Pass Lodge, Badlands National Park
The Hotel Alex Johnson, Rapid City, S.D.
Celebrity Hotel, Deadwood, S.D.
Red Rock River Resort, Hot Springs, S.D.
“The Ballad of Sally Rose,” Emmylou Harris
“I Got a Gal I Love (In North and South Dakota),” Frank Sinatra
“Deadwood,” Nancy Griffith
“Rocky Raccoon,” The Beatles
“Rapid City, South Dakota,” Dwight Yoakam