How Leading Literary Walking Tours Humanizes Writers of the Past

by Jessica A. Kent | July 6, 2026

It started with a selfie video back in October. As the founder and director of Literary Boston, I was toying with the idea of giving literary history tours, so I offered one to some friends. After I toured them around Beacon Hill, the Athenaeum, and downtown, to the places where authors of the past lived, gathered, and wrote, I made a video outlining our path through the city and what we saw.

And then I started getting comments, mostly from strangers: “When are these tours?” “This tour sounds amazing!” “Are you giving this tour this weekend?” “I checked your website and I don’t see a way to book?”

Ok, I guess I was launching a literary history walking tour! I created the Ink & Cobblestones Tour: A Walk Through Boston’s Literary Past, and launched a pilot beginning in November. All seven dates sold out within a week, and I’ve started up tours again for this year.

But all of this didn’t really start with a video last October. Instead, it started with a trip to Walden Pond in 1999. Nothing in my literature classes really resonated with me until 11th grade English, which was the American literature year. There was something about reading Dickinson and Whitman and Hawthorne and Emerson that struck something in me, and reading Walden was the first time I read something that made me think differently about the world. We took a field trip over to Walden Pond and I remember standing at the edge of the water thinking, “Henry David Thoreau stood here. This was the view he saw. And he wrote something 150 years ago that’s impacted me today. And I’m in the same spot in the earth as he was.”

So you could say I’ve always been interested in how people of the past are connected to place. Who’s stood here. Who was in the room. Who saw this same view looking through this same window? Who came before me in this place?

And how do I create a literary tour that captures that same feeling?

I’ve never necessarily been interested in author biographies. I know much of the gang lived in Concord, gathered at the Omni Parker House, published at the Old Corner Bookstore, and wrote at the Boston Athenaeum. Many of them lived in Beacon Hill.

But as I started putting together the tour, the broadness of biography needed to get very specific. I had to reduce the legacy of the greats (and lesser knowns, and unknowns) of literature down to moments lived in locations over finite periods of time. Instead of the story of their lives, what’s the story at this apartment building, at this corner, in this location, at this specific time in history? Who were they then? What were they writing? Was their life actually like mine?

Louisa May Alcott, the great author of Little Women, became 20-year-old Louy living at 20 Pinckney St., getting her first publications, trying to make it as a working writer, having visions of her future career. Her diaries at that time describe moments with her family that would turn into scenes in Little Women.

Nathaniel Hawthorne, the great author of The Scarlet Letter, became a guy with a day job at the Custom House, trudging up the hill at the end of a long day to 54 Pinckney to write in the hours he had left — something any working writer can relate to. Those walks around the city also likely inspired scenes from The Scarlet Letter: the graveyard next to King’s Chapel, the scaffolding where the Old State House is today, Hester’s hut on the edge of the Charles.

Sylvia Plath, the great author of The Bell Jar and Ariel, became a poetry student while living at 9 Willow, attending classes with Robert Lowell and catching a drink after with Anne Sexton, going to her day job at MGH, probably taking the T around town. She wrote from an apartment overlooking the famous (not then, likely) Acorn St. and penned a poem about Boston at the holiday season for her first publication in The New Yorker.

Phillis Wheatley, the first published African-American poet, became a teenager walking downtown Boston, watching the Revolution unfold outside her master’s home on State St. while Classical literature floated around her head, translating to words on a page dared to be written.

While creating the tour and now every time I deliver it, these authors of the past come down to Earth. They weren’t greats from the start. Humanizing writers of the past is encouraging as a writer. There wasn’t necessarily anything special about them. They had day jobs and took classes and trudged up Boston’s hills like we do today, with whole words in their heads yearning to get out on paper — like we do today.

Ultimately, they’re just the past iteration of the Boston literary community that continues on so strongly today. We’re really no different. We writers fit in writing between the day jobs, like Alcott and Hawthorne did. We meet for drinks and connect, like the Saturday Club did. I have friends who are booksellers, like Hezekiah Usher and Henry Knox were. I have friends who started a publishing company, trying to make a mark like Ticknor & Fields once did.

And that’s part of the reason why I’m running literary history tours: so that we remember this past and can hopefully be inspired by it today. Boston has such a rich literary past yet strangely lacks the storytelling around it to remind us of the creativity that once existed and thrived here. Freedom Trail-comparable literary trail initiatives have come and gone. The Literary District is defunct. The Old Corner Bookstore is a burrito shop. Plaques are lacking from many literary locations. And I’m sure if you asked Bostonians who the Longfellow Bridge is named after, they probably wouldn’t know it was the Fireside Poet.

We need that knowledge of the past. Boston wasn’t just the birthplace of the American Revolution. It was the birthplace of American Literature.

My literary history tour started with a video on social media. But it continues as an initiative to uncover literary history and have attendees experience that history by seeing the sites and reading the words. It’s the least I can do for the Boston literary community of the past.