A Literary Road Trip Through the Eastern USA: From Poe to Plath
There’s something magical about walking in the footsteps of the great American writers—seeing the streets they walked, the homes they lived in, and the landscapes that stirred their imaginations. If books have shaped your soul, a literary road trip through the eastern United States is your kind of pilgrimage. This curated journey takes you from the cobblestones of Boston to the swamps of the South, weaving through the words and worlds of America’s most celebrated literary figures.
Buckle up, set your GPS to “Bookish Dreamscape,” and get ready to explore the eastern USA one author at a time—with perfect soundtrack recommendations for the miles between.
Literary Road Trip Playlist – Music to Travel With
To set the tone between destinations, add these songs to your road trip playlist:
“America” – Simon & Garfunkel
“Moonlight Mile” – The Rolling Stones
“Bookends” – Simon & Garfunkel
“Night Moves” – Bob Seger
“River” – Joni Mitchell
“Road to Nowhere” – Talking Heads
“Going to California” – Led Zeppelin (even if you're staying East!)
“The Weight” – The Band
Stop 1: Boston, Massachusetts – The Cradle of American Literature
Begin your journey in Boston, where colonial history and literary greatness go hand in hand.
Must-See Spots:
The Old Corner Bookstore: Once the publishing hub for Thoreau, Emerson, and Hawthorne.
Boston Athenæum: A historic library frequented by Longfellow and Alcott.
Beacon Hill: Stroll through one of the city’s oldest neighborhoods, filled with gaslit streets and literary landmarks.
Just across the Charles River in Cambridge, you'll find Harvard University, where poets like T.S. Eliot and E.E. Cummings studied.
Wanderwood Tip: Grab a cup of coffee at Tatte Bakery and read a chapter of Walden before heading west.
Stop 2: Concord, Massachusetts – Transcendental Territory
A short drive brings you to Concord, the beating heart of the Transcendentalist movement.
Must-See Spots:
Walden Pond: Walk the trail around the pond where Henry David Thoreau lived in solitude.
The Old Manse: Home to Ralph Waldo Emerson and later Nathaniel Hawthorne.
Sleepy Hollow Cemetery: Visit "Author’s Ridge," where Emerson, Thoreau, Alcott, and Hawthorne are buried.
Wanderwood Tip: Stay at the charming Colonial Inn, where literary legends once dined and debated.
Stop 3: Amherst, Massachusetts – Emily Dickinson’s Quiet Revolution
Drive west into the Pioneer Valley to reach Amherst, home of the reclusive and revolutionary poet Emily Dickinson.
Must-See Spots:
Emily Dickinson Museum: Tour her home and learn how she wrote nearly 1,800 poems in private.
Amherst College Archives: Where many of her original manuscripts are stored.
West Cemetery: Dickinson’s final resting place, often decorated with notes from fans.
Literary Insight: Dickinson rarely left her home—your visit bridges that distance for her and brings her words into your world.
Stop 4: Hartford, Connecticut – Mark Twain’s Grand Imagination
Next, head to Hartford, where two greats once lived side by side: Mark Twain and Harriet Beecher Stowe.
Must-See Spots:
Mark Twain House & Museum: A stunning Victorian Gothic mansion where Twain wrote The Adventures of Tom Sawyer and Huckleberry Finn.
Harriet Beecher Stowe Center: Just next door, explore the life of the woman who wrote Uncle Tom’s Cabin.
Wanderwood Tip: Book a night at the Goodwin Hotel, a boutique stay with vintage flair in downtown Hartford.
Stop 5: New York City – Literary Legends and Beat Generation
No literary road trip is complete without a detour to the cultural capital of the country: New York City.
Must-See Spots:
The New York Public Library (Main Branch): Home to the original Winnie-the-Pooh and a stunning reading room.
Greenwich Village: Once the epicenter of the Beat Generation. Grab a drink at White Horse Tavern, where Dylan Thomas famously drank his last.
Hotel Chelsea: A haven for creatives, including Arthur Miller, Tennessee Williams, and Jack Kerouac.
Strand Bookstore: "18 miles of books" and an icon in its own right.
Wanderwood Tip: Explore the Literary Walk in Central Park and bring along Leaves of Grass by Walt Whitman.
Stop 6: Baltimore, Maryland – The Shadow of Poe
Head south to Baltimore, where the macabre meets the poetic in the city of Edgar Allan Poe.
Must-See Spots:
Edgar Allan Poe House and Museum: A humble row house where he once lived and wrote.
Westminster Hall and Burying Ground: Visit Poe’s grave and leave a rose like the mysterious “Poe Toaster.”
The Horse You Came In On Saloon: The last bar Poe was seen in before his mysterious death.
Playlist Pairing: Listen to “The Raven” narrated by Christopher Lee or play something haunting like Radiohead’s “Exit Music (For a Film)”.
Stop 7: Richmond, Virginia – Poe’s Southern Roots
While Poe is often associated with Baltimore, his formative years were spent in Richmond.
Must-See Spots:
The Poe Museum: Located in the oldest building in the city, it features letters, rare editions, and artifacts.
Monumental Church and Shockoe Hill Cemetery: Tied to Poe’s family and early life.
Wanderwood Tip: Richmond’s food and brewery scene makes it an ideal spot to unwind between heavy literary stops.
Stop 8: Asheville, North Carolina – Thomas Wolfe’s Mountain Melancholy
Drive into the Blue Ridge Mountains to reach Asheville, home of novelist Thomas Wolfe, known for Look Homeward, Angel.
Must-See Spots:
Thomas Wolfe Memorial: Visit his boyhood home and learn how Asheville shaped his complex characters.
Downtown Asheville: Full of indie bookstores, poetry slams, and cozy cafés with mountain views.
Literary Insight: Wolfe once wrote, “You can't go home again”—but here, you can visit where it all began.
Stop 9: Savannah, Georgia – Gothic Charm and Midnight Lore
Savannah is as rich in Southern Gothic atmosphere as it is in storytelling.
Must-See Spots:
Flannery O’Connor Childhood Home: Dive into the life of the queen of Southern Gothic.
Bonaventure Cemetery: Eerily beautiful, this cemetery features prominently in Midnight in the Garden of Good and Evil.
E. Shaver Booksellers: One of the best indie bookstores in the South.
Wanderwood Tip: Take a literary ghost tour to experience Savannah’s haunted history through its books.
Optional Final Stop: Key West, Florida – Hemingway’s Island Getaway
For those who want to go the distance, head south to Key West—Ernest Hemingway’s tropical paradise.
Must-See Spots:
Ernest Hemingway Home & Museum: Wander among six-toed cats and see the typewriter where Hemingway worked.
Sloppy Joe’s Bar: His favorite watering hole.
Key West Literary Seminar: If you're planning ahead, this annual January event draws writers and readers from around the globe.
Playlist Pairing: Add some island classics like Jimmy Buffett’s “Changes in Latitudes, Changes in Attitudes.”
A literary road trip through the eastern USA is more than a getaway—it’s a deep dive into the heart of American storytelling. From Poe’s haunted houses to Thoreau’s tranquil pond, this journey brings words to life and landscapes to meaning. Whether you're reading as you go or writing your own story along the way, you’ll come back richer, wiser, and maybe even a little haunted—in the best possible way.
Start your journey with Wanderwood Escapes—and let your next chapter begin.
