Boston Literary History Walking Tours

Walk in the footsteps of literary history…

Boston has a such a rich literary history, from the first printing press in the Colonies to fostering authors and literary movements that changed the world. Our history continues to inspire the great literary community that thrives in Boston today. It’s the past and present continuing on in parallel.

Explore that rich history today by walking in the footsteps of writers and literary luminaries that came before.

The Ink & Cobblestones Tour: A Walk Through Boston’s Literary Past

Walk through Boston’s literary history, from 18th century bookstores, to 19th century literary movements, to 20th century poets.

On this tour, you’ll learn about the writers who lived on Beacon Hill, Boston’s literary firsts, the oldest library in Boston, the hub of 19th century publishing, the site of the first bookstore in Boston, and some literary inspiration from a graveyard.

Guided by Jessica A. Kent, writer and founder of Literary Boston, this 90-minute walk connects Boston’s past to its present — from the salons and presses that shaped the city’s literary voice, to the communities still writing its next chapter.

You’ll walk away with a greater understanding of Boston’s literary history, as well as the experience of being in the same place where some of America’s greatest authors once stood.

Tour Details

Duration: 90 minutes

Tickets: $20 pilot rate

Group Size: 10 (minimum of 4 people to run; see FAQ for more details)

Location: Beacon Hill to Downtown

Terrain and accessibility: Hilly and uneven — bring appropriate shoes and stamina!

Weather: Tours run rain or shine — come prepared for New England weather! (In the case of very inclement weather, refunds or changes in booking will be offered.)'

Dates and Booking: November pilot program is now launched! Join some of the first literary walking tours Literary Boston is offering (and give me feedback on how I’m doing!).

Available dates:

All tours for the season are sold out! THANK YOU for an amazing kick-off!

The Ink & Cobblestones Tour will return Spring 2026 with dates throughout the year! Check back soon for new bookings.

Coming in 2026…

Crimson Quills

A Walk Through the Literary History of Harvard Square

UnCommon Authors

Literary History in the Neighborhoods Around the Common

The Handmaid’s Tale Tour of Harvard Square

Walk the locations in Margaret Atwood’s classic novel

Hawthorne’s Boston

Walk in the footsteps of Nathaniel Hawthorne and his characters

Your Tour Guide

Hi! I’m Jessica, and I’m the founder of Literary Boston, which I started in 2012 as a place as a website where people could find everything there was to know about the Boston literary community. But you could say that Literary Boston may have truly started on a trip to Walden Pond in 1999. I fell in love with the literary history of Boston then and I’m still fascinated with it today, so much so that I’ve made it a pillar of my work on Literary Boston.

For the past 25 years, I’ve been studying Boston literary history, from structured study in academic programs to reading historical markers all over the city. Now, I want you to know about our rich literary past, too.

A little bit more about me:

I’m a freelance marketing writer by day and creative writer by night. I’m the founder of Literary Boston, a website that covers the local literary community, and other past literary roles include library assistant, bookseller, and book festival director. I hold a BFA in Creative Writing from Emerson and a Master’s in Literature from Harvard, where my thesis on Moby-Dick and Calvinism won the Director’s Prize. My short fiction has appeared the North American Review, the Emerson Review, and others, and has received the Leah Lovenheim Award for Short Fiction. I recently graduated from GrubStreet's Novel Incubator program, where I’m working on a novel about paramedics in 1970s Boston.

If you would like to book me for a private walking tour, contact me through the form on the “About” page.

F.A.Q.

  • The Ink & Cobblestones Tour runs approximately 90 minutes, depending on pace and discussion. We’ll cover about one mile of walking with plenty of stops to talk, learn, and take photos.

  • You’ll receive a confirmation email with the exact meeting point after booking. The route begins on Beacon Hill and ends downtown near the historic Old State House — close to the T and plenty of cafes, shops, and even a bookstore for post-tour coffee or browsing.

  • We’ll walk at a comfortable pace, with frequent stops. The route includes hills — the tour was planned so you’re mostly walking downhill! — and uneven brick sidewalks typical of historic Boston, so comfortable shoes are a must!

  • All tours are led by Jessica A. Kent, founder of Literary Boston and creator of the Boston Literary History 101 course. Jessica has spent over a decade researching, writing about, and connecting Boston’s literary past and present — and she’s excited to share those stories with you! Read a bio below.

  • Groups are capped at 10 to encourage conversation and connection.

    Please note: Tours require a minimum of four registered participants to run. In the rare case that fewer than four people sign up, you’ll be notified 24 hours in advance and offered a full refund or reschedule option.

  • Tours run rain or shine! Please dress appropriately for the weather—umbrellas and layers are encouraged. In severe weather (thunderstorms, heavy snow, etc.), you’ll be notified of cancellation and offered a full refund or reschedule.

  • Cancellations made at least 48 hours before the tour will receive a full refund. Within 48 hours, tickets are non-refundable but may be transferred to another date (if available).

  • Boston’s historic sidewalks can be uneven and narrow in places, especially in Beacon Hill, which is where half of the tour takes place. Reach out and we can talk through options. Look for accessible tours in the Spring!

  • Absolutely! Please tag @literary_boston on social media if you post, as sharing helps others discover Boston’s literary history too. I just ask that you refrain from filming large chunks or the whole thing.

  • Yes! I’m happy to arrange private tours for schools, book clubs, corporate outings, or visiting groups. Use the contact form to inquire about rates and custom scheduling.