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.)

October Special: Ink & Cobblestones AFTER DARK

Experience Boston’s literary history after dark! This October, join a special evening edition of Ink & Cobblestones, exploring the streets of Downtown and Beacon Hill by night — with a few special additions and surprises along the way.

Upcoming dates

  • Saturday, September 12 at 11:00am

  • Saturday, September 26 at 11:00am

  • Saturday, October 2 at 6:30pm *Ink & Cobblestones AFTER DARK

  • Saturday, October 10 at 11:00am

  • Saturday, October 10 at 6:30pm *Ink & Cobblestones AFTER DARK

  • Saturday, October 24 at 6:30pm *Ink & Cobblestones AFTER DARK

  • Saturday, October 31 at 11:00am

  • Saturday, November 14 at 11:00am

  • Friday, November 27 at 2:00pm *Special Black Friday tour!

  • Saturday, November 28 at 11:00am

  • Saturday, December 12 at 11:00am

Book now

Other Upcoming Tours

Saturday, September 12 at 11:00am:

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

Saturday, September 19 at 11:00am:

The Crimson Quills Tour: The Literary History of Harvard Square

Saturday, September 26 at 11:00am:

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

Saturday, October 3 at 11:00am:

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

Interested in a group tour booking? Head here.

What They’re Saying…

“Highly recommend taking a tour with Jessica! It felt like exploring Boston with a brilliant, down-to-earth local friend. It was super fun to take a step back in time and walk in the footsteps of Boston's literary figures. Jessica is an engaging storyteller who shares fascinating, lesser-known facts. Don't miss out!” - Siham, Ink & Cobblestones

“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

“Boston’s literary history comes alive! What a lovely way to spend a morning—walking the streets of Beacon Hill and State House area and learning of all the esteemed writers that lived and created here in our city. Jessica was extremely knowledgeable and told many stories as she pointed out lodgings and meeting places.” - Donna, Ink & Cobblestones

“Exceptionally thoughtful planning and execution. I learned a ton and enjoyed the tour immensely.” - Jeff, Ink & Cobblestones

“I learned so much and discovered corners of Boston I didn’t even know about. The tour was entertaining, informative, and the readings of literature and poetry along the way were wonderful.” - Tour attendee, Ink & Cobblestones

“I loved that the tour was not only about the canonical authors we know and love, but also covered abolitionist and black writers we should all know better! Great choice of excerpts and poetry, the perfect complement to the tour. We had so much fun!” - Annelise, Ink & Cobblestones

“You are an amazing tour guide! The details you shared about each site and each essay/speech/poem were clear, compelling, and memorable. I love thinking about how words and rhetoric influence history, so this was right up my alley. The tour was just the right length, and reading the snippets of the revolutionary words out loud felt strangely emotional, in a good way. I love that you encouraged us to do that, rather than just have the entire tour consist of you reading everything.” - Allison, Revolutionary Words

“I loved the intimate small group. I learned quite a few things that I didn’t know before. The readings added something very special. I would 100% take this tour again or one of the others offered.” - Delcie, Revolutionary Words

“This tour was fun and informative! Jessica was very organized and an engaging speaker. I learned new facts about buildings that I have passed every day for years, and it was a unique touch to read texts out loud together in association with the places we visited. I highly recommend this tour!” - Pamela, Revolutionary Words

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).

  • This is a 90-minute walking tour covering approximately 1 miles over city sidewalks, including uneven surfaces, curbs, stairs, and occasional sidewalk construction. Some stops include visual materials/readings. If you have accessibility needs or would benefit from accommodations to participate comfortably and safely, please contact me before your tour so I can discuss the route and available options.

  • 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.