The Huck Finn
Sure, this is best done on a wooden raft. But Mark Twain won't object if you jump in the Subaru to follow the Great River Road along the legendary path of the Mississippi, the world's fourth-longest river. Just make sure you get along as famously with your fellow road trippers as Huck got along with Jim. Don't miss the Mark Twain Boyhood Home and Mark Twain Museum in Hannibal, Mo.
The route
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
Galena, Ill.
Hannibal, Mo.
Ste. Genevieve, Mo.
Trail of Tears State Park, Mo.
Memphis
Helena, Ark.
Indianola, Miss.
Vicksburg, Miss.
Natchez, Miss.
New Orleans
Playlist essentials
"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
Route 66
Epic and enchanting. Retro, rundown and revitalized. There are as many adjectives to describe Route 66 as there are ways to drive it. Do you want to hit the big towns on the way, where you'll find diverse dining options and city amenities, or sleep in vintage motels in the not-quite-middle-of-nowhere? Will you choose a section, or brag that you conquered every mile of what John Steinbeck famously called "the Mother Road?"
The route
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.
Playlist essentials
"(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
For Minnesotans, South Dakota often gets short shrift in favor of journeys east. This road trip includes an enchanting trinity of sights — the Badlands, the Black Hills and eastern Wyoming's Devil's Tower. Consider stopping for a photo and a postcard at kitschy favorites like Wall Drug and Deadwood, S.D. Contemplate U.S. history at majestic Mount Rushmore and the sobering Crazy Horse Memorial. Just over the Wyoming border, Devil's Tower lies in the serene prairie outside of the Black Hills: sacred to the Lakota, it's also practically holy to rock climbers. While you pack, watch Terrence Malick's 1973 film "Badlands," the original road-trip-gone-wrong movie.
The route
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.
Playlist essentials
"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
