The Oregon Trail by Francis Parkman (Dover, $11). Parkman was one of the 19th century's finest historians. His evocation of the old American West, which he glimpsed on an 1846 journey on horseback, is without parallel. Though occasionally marred by the racial prejudices of Parkman's day, his portraits of prairie Indian tribes are largely good-hearted and quite often droll.
Life on the Mississippi by Mark Twain (Signet, $5). Twain's wit is as sharp today as it was 130 years ago. The book's first part, depicting his apprenticeship on a steamboat, vividly portrays the romance of life on the river. The latter half, written several years later, has a more elegiac tone. By then the river, no longer the main way to travel the country, has lost much of its allure.
On the Road by Jack Kerouac (Penguin, $17). Exuberant, raunchy, and wild, this book spoke to the Beat Generation much like Hemingway's The Sun Also Rises did to the post–World War I Lost Generation. Read the unexpurgated "scroll" version, which Kerouac wrote on a continuous roll of paper in an amphetamine-fueled rush.
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Travels With Charley by John Steinbeck (Penguin, $11). Steinbeck's chronicle of an epic 1960 road trip with his poodle is a traveler's tale, a self-portrait, and a portrait of America at the advent of a tumultuous decade. The chapter portraying "the Cheerleaders" — a band of racist white women protesting a New Orleans school's integration — is devastating in its understatement.
Blue Highways by William Least Heat-Moon (Back Bay, $16). Faced with the loss of his job and his wife in 1978, Heat-Moon (the pen name for William Trogdon) embarked on a 13,000-mile journey across the U. S. His account of it is a marvelous classic of American literature.
The Adventures of Augie March by Saul Bellow (Penguin, $17). Bellow's 1953 coming-of-age novel melds street-smart swagger with literary elegance, and affected me deeply when I first read it, in a sweltering tent in Vietnam in 1965. Augie's journey through Chicago and into Mexico, meeting hustlers, geniuses, and eccentrics of every stripe, becomes our own. I swear it helped me get through the war.
— Philip Caputo traveled 16,000 miles, from Key West, Fla., to Alaska's North Slope, to create a fresh portrait of America for his new book, The Longest Road.
