The Ink & Cobblestones Tour

A Walk Through Boston’s Literary Past

See the sites. Read the work. Experience literary history.

Have you ever stood somewhere and realized: “This is where an author from the past stood — someone who wrote something that’s impacted me today?”

That’s the experience of the Ink & Cobblestones tour. As we walk the streets of Boston where writers from the past lived, gathered, and wrote, you’ll see that the past and present really do carry on in parallel…

On this tour, you’ll learn about the writers who lived on Beacon Hill, 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.

Along the way, we’ll read work by the authors we encounter, including Phillis Wheatley, Louisa May Alcott, Nathaniel Hawthorne, Sylvia Plath, Robert Frost, and more.

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.

View a trailer here!

“I really enjoyed how being physically present in the moment gave me glimpses into the lives of different writers who once shared the same spaces, it felt like a thread connecting all of us. Walking the streets and seeing each corner through their eyes made the experience feel alive.” – Lena, Ink & Cobblestones

TOUR DETAILS

Duration: 90 minutes

Tickets: $40

Group Size: Limited to 10 (minimum of 5 people to run)

Location: Downtown to Beacon Hill

Your Guide: Jessica A. Kent, founder and director of Literary Boston

Stops include: Omni Parker House, Boston Athenaeum, the Old Corner Bookstore, the residences of Louisa May Alcott, Nathaniel Hawthorne, Robert Frost, and Sylvia Plath, and more!

Distance: A little over a mile

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

Weather: Tours run rain or shine. (In the case of very inclement weather, refunds or changes in booking will be offered. See FAQ below.)

Upcoming dates

  • Saturday, July 25 at 11:00am

  • Saturday, August 15 at 11:00am

  • Saturday, August 29 at 11:00am

  • Saturday, September 12 at 11:00am

  • Saturday, September 26 at 11:00am

  • Saturday, October 10 at 11:00am

Book now

Other Upcoming Tours

Saturday, July 25 at 11:00am:

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

Saturday, August 1 at 11:00am:

Revolutionary Words: A Literary Walk Through the Writings that Inspired Independence

Saturday, August 15 at 11:00am:

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

What They’re Saying…

“The walk, the information, your joyous presentation were all fun.” – Ellen, Ink & Cobblestones

“This was great for me as someone who doesn't know a lot about Boston history outside of what we're taught in US history.” – Tour attendee, Ink & Cobblestones

“Loved the short readings in front of relevant locations!” – Sarah, Ink & Cobblestones

“I loved being immersed in the sense of Boston as a literary community. And realizing that books were important to Bostonians, even in the colonial era. And that in the 19th century, when so many writers lived in Boston, they knew each other and congregated in places like the Old Corner Bookstore. It's a great sense of community that I think continues on.” – Kathleen, Ink & Cobblestones

“I really enjoyed how being physically present in the moment gave me glimpses into the lives of different writers who once shared the same spaces, it felt like a thread connecting all of us. Walking the streets and seeing each corner through their eyes made the experience feel alive. I especially loved hearing how a tombstone in the old burial ground inspired The Scarlet Letter, and learning about Fanny Goldstein and her role in creating Jewish Book Month.” – Lena, Ink & Cobblestones

“I enjoyed being able to read passages written from the authors about the locations we visited. I felt like it was a great way to keep the tour interactive. It also showed how much time and effort you put into researching for your tour. I enjoyed seeing the photos on your tablet. I also liked that you were very open to questions and excited about us being on the tour with you. All of my friends loved the tour and we talked about the tour for a couple days after.” – Tour attendee, Ink & Cobblestones

“The readings! Well-chosen spots that give a good sense of both American and Boston history.” – Marisa, Ink & Cobblestones

“Learning about the Beacon Hill connections of Robert Frost, Sylvia Plath, and a few others. The readings were a great innovation.” – Elizabeth, Ink & Cobblestones

“Liked seeing the tombstone with the engraved "A" that may have inspired Hawthorne, and really enjoyed the excerpts selected for the group to read.” – Denise, Ink & Cobblestones

“Reading various passages made the tour so much more experiential.” – Tour attendee, Ink & Cobblestones

“Walking through the neighborhoods of Boston, connecting the content to real life people and places. Knowledge of guide.” – Heather, Ink & Cobblestones

“Walking and talking, with well timed rests and breaks. Great pace. So many authors and sites included in the tour. Snow flurries in Beacon Hill...all the sites were interesting and appealing. Non-stop learning for 90 minutes. Great value for ticket price.” – Elizabeth, Ink & Cobblestones

“I liked the printed literature that everyone had a chance to read. I love walking around Boston.” – Sarah, Ink & Cobblestones

“I liked being able to learn things about places I have walked by a million times. I often forget that a lot of the older writers knew each other so it was fun to learn about how they interacted. I appreciated how women were highlighted as well.” – Amanda, Ink & Cobblestones

“Jessica is an engaging tour guide who has spent years researching local history; she's so passionate about her work that her tour is an absolute delight. I've been to Boston often, and I learned a lot from "Ink and Cobblestones"! I now have a new appreciation for the literary history surrounding the Beacon Hill area.” – Lori, Ink & Cobblestones

“Jessica's contagious enthusiasm for her subject.” – Marylisa, Ink & Cobblestones

“I loved the literary quotes mixed into the historical narrative. So fun and informative!” – Lisa, Ink & Cobblestones

“Learning about writers I hadn't heard of or knew little about, and the inclusion of so many women. We see or pass many of the stops on the tour often, but have a very different appreciation of them now!” – Tour attendee, Crimson Quills

Your Tour Guide

Hi! I’m Jessica, and I’m the founder and director 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 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.

F.A.Q.

  • The Ink & Cobblestones Tour runs approximately 90 minutes. 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 at the Old State House and ends on Beacon Hill — close to the T and plenty of cafes, shops, and even a bookstore for post-tour coffee or browsing.

  • We’ll walk about a mile, at a comfortable pace, with frequent stops. The route includes hills and uneven brick sidewalks typical of historic Boston, so comfortable shoes are a must!

  • All tours are led by Jessica A. Kent, founder and director of Literary Boston. 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 above.

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

    Please note: Tours require a minimum of five registered participants to run. In the rare case that fewer than five 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.

  • For public tours, 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! Head here to learn more.