For this literary road trip to Boston, we’re not only traveling from location to location in the city of Boston but also through the centuries. Phillis Wheatley, the first published African American author, represents the 18th century. The 19th century brings us Edgar Allan Poe and Edward Everett Hale. And finally, the 20th century is exemplified by David Foster Wallace. Most of our literary road trip centers on downtown Boston, with stops at the Boston Public Garden, the Boston Common, and other sites along the Freedom Trail. We’ll venture to other areas of the city, too, such as Castle Island in South Boston, Roxbury, and Jamaica Plain.
Phillis Wheatley
Wheatley was born in West Africa and sold into slavery in the Colonies. Purchased by John and Susanna Wheatley, she was named “Phillis” for the ship she sailed on. Wheatley would become the first published African American poet. Although enslaved, Whealey espoused the quest for American independence during the period leading up to the American Revolution. After the publication of her poetry book in 1773, Whealey was granted her freedom. At only 31 years of age, she contracted pneumonia and died.
Our Literary Road Trip to Boston brings us first to the Boston Women’s Memorial on the Commonwealth Avenue Mall. Walking through the Back Bay and into downtown, we arrive at the Granary Burying Ground. Although the location of Wheatley’s interment is lost to history, some scholars believe it to be Copp’s Hill Burying Ground. John and Susanna are buried at Granary. Just down the street is the Old South Meetinghouse, which was the church that Wheatley attended. Also nearby, at the corner of Kilby and State Streets, was the site of the Wheatley home, since demolished. Nearby at King’s Chapel is the newly constructed Memorial to Enslaved Persons. Although not related to Wheatley directly, this memorial commemorates the plight of the 200 enslaved persons associated with this congregation.
Edgar Allan Poe
Although more associated with cities such as Baltimore (heck, even the football team is named for his work), Philadelphia, and New York, Edgar Allan Poe, master of the macabre, was actually born in Boston. Unfortunately, for young Edgar, his father left his family a year after he was born. The family would leave Boston for Richmond, Virginia.
His tenure in Beantown was short, but there are still stops for him on our literary road trip of Boston. Starting at the Transportation Center on Charles Street South, this was the location of Poe’s Boston home. Nearby, at the corner of Charles Street and Boylston, is a life-sized statue depicting Poe walking. References to his poems in this sculpture include a gigantic raven bursting out of his briefcase and a heart on top of a pile of books. The sculptor chose the well-known poem “The Raven” and the short story “The Tell-Tale Heart” to further characterize Poe. As a soldier, Poe was stationed at Fort Independence on South Boston’s Castle Island. Today, it’s a park ripe for exploration. Popular lore surrounding the fort involved a duel and a live entombment, both of which gave inspiration for his “The Cask of the Amontillado.”
Edward Everett Hale
Historian and writer Edward Everett Hale was a Unitarian minister and an abolitionist. He wrote both fiction and nonfiction works, with his most famous being The Man Without a Country. He also wrote a history of the state of Massachusetts. Hale is memorialized by a lifelike statue in the Boston Public Garden sculpted by Norwich, CT’s own Bela Pratt, also known for statues of Nathan Hale, the Art and Science figures flanking the doors of the Boston Public Library, and the Andersonville Boy in Hartford.
For the rest of Hale’s journey, let’s hop in the car. He lived in a stately Greek Revival home on Morley Street in Roxbury Highlands. This section of the neighborhood has stunning architecture. Napoleon Jones Henderson, an artist, lived in the home for 50 years before passing away in 2025. The house is not open to the public, but can be easily seen from the road. The next stop is Hale’s gravestone. Its location in Forest Hills Cemetery is close to the rear entrance, across the street from the Forest Hills crematorium. His grave is located on Ageratum Path. It’s a modest stone compared to many ornate fixtures in this Victorian-era cemetery.
David Foster Wallace
The contemporary author of our Literary Boston Road Trip is David Foster Wallace. Although Wallace was not a local, as he grew up in Illinois, he went to Amherst College in Massachusetts, as well as the University of Arizona. He taught briefly at Emerson College, which flanks the southeastern side of Boston Common.
His opus, Infinite Jest, takes place in the fictitious town of Enfield (well, there was an Enfield, MA, that was submerged to create the Quabbin Reservoir, but that’s another story). Enfield’s location is in the Allston-Brighton neighborhood. The book has references to many locations throughout Cambridge and Boston. There are essays written about the locales of the book on the website InfiniteBoston. Since this literary road trip has taken us downtown, the draining of the lagoon in Boston Public Garden is mentioned, and during my latest visit in March 2026, it was actually devoid of water. Places in and around the Boston Common are named in Infinite Jest, including the Massachusetts State House and the Park Street subway station. Even the Robert Gould Shaw Memorial is mentioned in the book.
Four different authors from three different decades have taken us through this Literary Road Trip in Boston. Centered around downtown, this journey includes visits to the Boston Public Garden and Boston Common, with walkable sites on or near the Freedom Trail. Hop in the car to enjoy Edward Everett Hale’s home and resting place in Roxbury and Jamaica Plain, respectively, as well as to visit the inspiration for a Poe story in South Boston.
Still curious? Try this literary road trip to nearby Concord, MA. Or stroll through Boston in the footsteps of Jonathan Richman.
