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America's Best Literary Road Trips

Follow the routes of the classic road-trip writers

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21 September 2021 by Rachel Mostyn

Wexas USA specialist Rachel Mostyn picks out her favourite reads to accompany the USA’s most iconic road trips. 

Pacific Coast Highway – Big Sur, Jack Kerouac

“The more ups and downs, the more joy I feel,” opines Jack Kerouac in his fictionalised biography, Big Sur. It’s a statement that applies as much to the author himself as it does the novel’s eponymous road – a spectacular route that maps the Californian coast where the Santa Lucia Mountains rise abruptly from Pacific cliffs. It’s a rollercoaster of bridge hops, long lefts and sweeping rights. But, it forms just a 71-mile segment of the Pacific Coast Highway, a 665-mile epic that links San Francisco and Los Angeles, offering stops at pretty vineyards, Monterey’s dolphins and a fantastic choice of white-sand beaches.

Take a look at our Pacific Coast self-drive

Florida – Ernest Hemingway

While Hemingway’s oeuvre spans from Africa to war-torn Europe, the great author himself chose to take up residency in the Florida Keys. And, with good reason. A paradise archipelago of palm-fringed islands, it divides the Atlantic and Gulf of Mexico, forming a postcard-perfect spread of idyllic beaches. It’s all knitted together by a network of scenic bridge crossings, making for a truly epic drive that concludes with a chance visit to Hemingway’s home itself, found in idyllic Key West. Then, back on the Florida mainland, you’ll be treated to Spanish-colonial heritage, Miami’s glitz and glam, and Naples, a bohemian beach retreat.

Take a look at our Florida self-drive

Route 66 – The Grapes of Wrath, John Steinbeck

Connecting Chicago to Los Angeles, the Mother Road maps the route taken by the migrants who headed west to escape the Great Depression of the 1930s. It’s a journey shared by thousands and immortalised in one of Steinbeck’s greatest works, The Grapes of Wrath. And today it remains the ultimate road trip for those who want to get a taste of the famous American optimism. Indeed, from the ghost towns of the Mojave Desert to the open cornfields of Illinois, there’s a pervading sense of a romantic past to it all. You’ll also have the chance of happy detours to Las Vegas and the Grand Canyon before ending with some well-deserved relaxation on the beaches of Santa Monica. It’s a far cry from the hardship faced by Steinbeck’s characters.

Take a look at our Route 66 self-drive

New England – The Crucible, Arthur Miller

Given that much of America’s early history is tied up in this six-state huddle, it’s no surprise that New England is rich with literary tradition. I could have picked any of the great Romantic writers, from Thoreau to Dickinson, but few capture the region’s puritanical intensity as well as Arthur Miller’s The Crucible, a dramatisation of the Salem witch trials. Indeed, a road trip to New England is a step into the past; highlights include the Civil War battlefields, the colonial-era charm of Newport, and Boston, where cobbled laneways lead between some of the country’s most important sites. Of course, there’s plenty of scenery to enjoy on your road trip as well, including the Green Mountains and the quaint seaside villages of Cape Cod.

Take a look at our New England self-drive

Canyon Country – Fear and Loathing in Las Vegas, Hunter S. Thompson

No other author captures the decadence and pure eccentricity of Las Vegas quite like Hunter S. Thompson, who brings out all of its contradictions in a whirlwind of manic prose. But, just as his best-selling novel heads out for a drive in the desert, so should you. Sublime routes bring you between the flat-topped mesas of Monument Valley, the spindling arches of Moab and that great national wonder – the Grand Canyon. Together, they constitute a selection of some of America’s finest national parks, with further highlights including the Bryce Canyon’s hoodoo spires and Zion, where dirt-red rock formations contrast with valleys of bright verdure – perfect for ranging hikes.

Take a look at our Canyon Country self-drive

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