To explore the Alaskan wilderness yourself, make the scenic drive from Fairbanks to Denali, then hop a bus to Wonder Lake.
(Courtesy BillC/Wikimedia Commons)
McCandless's adventure has sparked interest in the Stampede Trail, where visitors seek out Bus 142, the abandoned bus where he took refuge and later died.
(Courtesy Erikhalfacre/Wikimedia Commons)
The South and Southwest come alive as Wyatt (Peter Fonda) and Billy (Dennis Hopper) discover themselves and America in the 1960s counterculture classic Easy Rider.
(Courtesy Environs/Wikimedia Commons)
Taos, N.M., is the site of several Easy Rider scenes. As you pass through, carve out an afternoon to tour the UNESCO World Heritage Site of the Taos Pueblo.
End your Easy Rider tour in New Orleans and visit St. Louis Cemetery No. 1, where the guys' infamous bad trip went down.
Much of Easy Rider takes place along Route 66, which is overlapped today by parts of I-40. If you begin where the twosome hit the open road, in Death Valley, Calif., then, like the boys, you'll be ready to refuel by Flagstaff, Ariz.
Sideways is a tour through one of the less-trafficked areas of California wine country, the Santa Ynez Valley.
(Courtesy Jester7777/Wikimedia Commons)
In Buellton, you can dig into Miles's (Paul Giamatti's) favorite smoked-then-grilled duck breast with apricot-ginger sauce, at the Hitching Post II restaurant.
(Kirk Irwin Photography)
One stop on the duo's ramble through the region is Foxen Winery & Vineyard in Santa Maria, where Miles and Jack (Thomas Haden Church) refill their glasses to the brim when the pourer's not looking.
(Courtesy Foxen Winery)
Wrap up your Sideways trip in Santa Ynez, a gateway village for Los Padres National Forest, where you can preempt a Giamatti-style wine belly by hiking the famous trails.
National Lampoon's Vacation traces the classic cross-country route of the Griswold family, from their home in Chicago to St. Louis, Kans., the Grand Canyon, and Los Angeles.
(Courtesy Daniel Schwen/Wikimedia Commons)
From your starting point in Chicago, drive down to St. Louis for a look at the Gateway Arch and its Museum of Westward Expansion.
(Courtesy Bev Sykes/Wikimedia Commons)
End in Anaheim, so that the kids can experience that real-life inspiration for Walley World that's never "closed for repairs"—Disneyland.
(Courtesy Tom Arthur/Wikimedia Commons)
Thelma & Louise director Ridley Scott actually shot all of the desert scenes in Utah. Plan your trip from Bryce Canyon (shown here) to Dead Horse Point.
(Courtesy Chmehl/Wikimedia Commons)
Dead Horse Point is where Thelma and Louise's final flight into movie history was filmed. Canyonlands and Dead Horse Point offer opposing views of one gorgeous chasm.
(Courtesy Jean-Christophe BENOIST/Wikimedia Commons)
In southwest Utah, Bryce Canyon is home to otherworldly orange rock formations that seem to morph in color and shape throughout the day.
(Courtesy Lucag/Wikimedia Commons)