The Origin of the Ink & Cobblestones Tour
How a Selfie Video Uncovered the Demand for Boston Literary History Tours
by Jessica A. Kent
May 21, 2026
Even though I put the Ink & Cobblestones Tour pilot together in a week in October 2025, I like to say that I had been writing the tour in my head for 15 years.
Boston’s literary past has always been an interest area of mine, ever since I stood at the shores of Walden Pond on an eleventh grade field trip 25 years ago, realizing that Thoreau had stood in the same place as me once and stared out at the same view. The fact that I could stand in the same spot as someone who wrote a book 150 years earlier that impacted me today felt to me like I found a way to time travel, to collapse the past and present together.
American Literature was where I was drawn to, where I read widely, and what I studied in both undergrad and in my master’s program, as many American Lit courses as I could take (which wasn’t many in a general literature/English program). I wrote my master’s thesis on Moby-Dick. For the month or so that I looked at doing a PhD, I knew it would be in American Studies or American Literature, with a focus on 19th c. New England or Boston-area writers.
But I didn’t do a PhD. I wanted to connect to people in the community about literature, do (what I now know is) public history, not keep all of that interest and conversation in academia. My master’s thesis advisor even said that I was more of a “pop lit” person, bringing literature to the people.
When I started Literary Boston in 2012, it was only natural that literary history would be part of the website and part of the content I shared: covering the literary community present AND past. It’s been a section on my website since then, a section in my weekly newsletter, literary history tidbits on social media, and a collection of articles.
Launching a walking tour was never on my mind — or, rather, it was something I thought I could test out someday. Yet when I’m with friends or just on my own walking through the city, I point out literary history sites: this author lived here, this group met here, this was published here, this gravestone inspired this. I know the route, and the stops, and the stories.
And I’ve found that people are generally interested in the literary history I share. But I didn’t realize how interested.
The First Test Tour and the Viral Video
In October 2025, I researched, wrote, recorded, and compiled “Boston Literary History 101,” a 70-minute on-demand video course that traces Boston’s literary history from the first printing press to what’s going on in today’s community over eleven lessons. I was set to launch that on October 24. The day before, a friend invited me to lunch in Beacon Hill to meet some of her writer friends from out of town. Since the history was fresh in my mind, and since we were meeting in Beacon Hill, I offered to show the group around to some of the literary history sites there, if they were interested. The answer was “Yes!”
I put together some notes, mostly from my own knowledge but also from some research, and gathered some poems, journal entries, and excerpts we could read aloud at these locations. That’s what felt natural to me: show the stop, give the story, read some work aloud together.
This informal walk started where Robert Frost lived on Mt. Vernon, where we read aloud “Nothing Gold Can Stay,” then continued on to Sylvia Plath (9 Willow), Nathaniel Hawthorne (54 Pinckney), Louisa May Alcott (20 Pinckney), Henry David Thoreau (4 Pinckney), and Elizabeth Palmer Peabody (15 Pinckney). We then walked down the hill to the Boston Athenaeum, where I, as a member, took my guests upstairs and showed them around. Then we continued on to the Omni Parker House, where the Saturday Club met and to show them the Dickens Door, then to King’s Chapel Burying Ground to show them The Scarlet Letter gravestone. (At this point, my friend leaned towards me and asked, “How do you know all this??” “Doesn’t everyone kind of know all this?” “No, Jess!”) We finished up outside the Old Corner Bookstore, once the hub of publishing in America, now a burrito shop.
They all loved it, gave me lots of great tips for a future tour if I ever want to launch this formally, and we parted ways. I got a coffee and went to my bench on the waterfront to take a rest. But since I had been starting to increase my visibility on Literary Boston through selfie videos, I thought, “Let me recap the tour. It’ll be a great teaser for my digital course!” (Spoiler: The digital course launched to little fanfare and was left in the dust of literary tours.)
I recorded a one-minute selfie video recapping my “first literary history tour” and the stops we visited, and then I posted it to my Literary Boston Instagram. I also found that I had 900 followers on a dormant Literary Boston TikTok account, so I posted there, too. Why not?
The likes started coming in. The “This is so cool!” comments started coming in.
And then the questions started coming in, from strangers:
“Where can I book this?”
“When are you running these?”
“Where can I sign up?”
“Are you running them next weekend?”
“I checked your website and I don’t see anything.”
“My daughter’s coming to town and we’d love to book!”
Hundreds of likes. Thousands of views. Dozens of comments.
I guess I was launching a literary history tour!
The Pilot Goes Live
I had enough data and interest to realize this could be a real thing. So the next step was to test it. I planned a four-Saturday pilot program for a 90-minute tour through Beacon Hill and downtown, and I called it The Ink & Cobblestones Tour: A Walk Through Boston’s Literary Past. I planned to announce it in my newsletter on Friday, October 31, one week later, with tours launching on November 8.
On that Monday, October 27, I launched a new tour page on Literary Boston, with graphics, copy, and ways to book through the site. By Tuesday, Google had already indexed the page and it was coming up first in search for “Boston literary history tours.” On Wednesday — two days before I even publicly launched anything! — I received an email from a school group out of state wanting to book a private Ink & Cobblestones tour the following Spring. (I had no private tour copy or system yet, but I figured it out.)
The other thing I needed to figure out was if I could actually just start leading tours in the streets of Boston. Boston does not require a tour guide license, but were there insurance issues? Fees? Other licenses? I reached out to one of my tour guide friends to check before I launched, and it was all a go.
Then, on Friday, October 31, I publicly announced the Ink & Cobblestones four-date pilot on my newsletter and on socials. And a booking came in. Then two. Then three. My phone was pinging all night. Three of the four dates sold out over that weekend, so I added three more dates. All of them sold out within a week. Some bookings were from friends. The rest were from people I didn’t know.
I had demand. I had sales. I just needed a tour to deliver.
Constructing the Tour and How to Be a Tour Guide
I was already coming into the Ink & Cobblestones Tour with a lot of previous knowledge about the spots I would bring people and what the route would look like, but what I really had to ask was, “What is the story at this particular location?” I can talk a lot about Lousia May Alcott’s life, but what was she up to here at Pinckney St. in her early 20s? Same with Hawthorne, same with Plath, same with Wheatley.
One of the distinctions about this tour is that we read work aloud along the tour route. It never occurred to me not to have readings be an integral part of the experience. So I went digging for work that was written at or inspired by the location, not necessarily a piece of work the author wrote at another time. I found great pieces about what it was like to visit Ticknor & Fields, Emerson’s son’s commentary about the Saturday Club, and a poem Plath wrote about Boston at the holiday season when she resided in Beacon Hill. Those readings went into a packet I would hand out to attendees.
I wanted to show photos or illustrations as well along the way, so people can see or visualize who I’m talking about. I really dislike the printed docs tour guides show in a binder in those plastic slips, so I dug out my old, unable-to-be-updated-anymore iPad mini from, like, 2013, that can’t do anything anymore except…show photos. That has been my trusty little tour companion.
There was also the danger that a classic tour mostly focused on the 19th c. would skew heavily white male writers. Where possible, I included women, minorities, and people of color to highlight — and attendees noticed that in the feedback.
I had the map, the notes, the readings, the iPad…but could I actually do this? Could I present, engage, do public speaking, hold attention for 90 minutes? I’ve never had issues with public speaking, thankfully, though I’m terrible at memorizing, so would be on book for the pilot. And it’s no problem for me to talk about literary history for hours! Thankfully, as I began to think through the experience of tour hosting, it felt more and more like my bookseller days, and providing customer service by greeting, leading, helping, and hosting.
I could do as much practice as I wanted, but nothing can prepare you for the first live tour. It just has to happen. You just have to do it and go from there.
As I walked to the meeting spot in Louisburg Square for the very first tour and waited for attendees — four friends, but the rest strangers — I kept thinking, “Am I doing this? What am I doing! Am I really going to do this?” And I was nervous as hell.
Run One, Iterate, Run Again, Keep Going
That first tour was clunky, but amazing. I looked at my notes a lot, I forgot to show some pics on the iPad, and we went 20 minutes over. But attendees enjoyed the experience, gave great feedback, and posted about it on social. I looked to see what I could cut down on to make the next tour go faster, and I was a little bit more off book for Tour 2.
But I realized that while starting in Beacon Hill and going to downtown let us go downhill, the tour was going in reverse chronological order. I was getting feedback that attendees were missing the connections, plus didn’t like ending in noisy downtown. So for Tour 3, I flipped the route, having us start at the first bookstore in the Colonies in downtown, and winding uphill into the 18th, 19th, and eventually 20th century. I found the natural path of the tour then.
I tested running a tour on Black Friday afternoon, which also sold out, and was the coldest one of the stretch, tour attendees huddling in puffy jackets yet staying with me right to the end. On the December 6 tour, we were surrounded by holiday decorations on Beacon Hill, light snow coming down as I read Plath’s poem about Boston at the holidays — a perfect ending. On December 13, the last tour, I offered attendees a few extra stops, and we finished reading a Longfellow poem about the Charles River on the Longfellow Bridge.
Over the seven tour dates, I saw which stops, readings, and jokes resonated, and which didn’t. During the pilot, I gathered feedback from attendees, finding that for over half of them, half or most of the tour content was entirely new. Many loved the added elements of the readings in place. Most said they would look at the city or an author differently now with what they had learned.
Overall, the tour pilot — and now well into a 2026 tour season, with a handful of private tours already booked — showed me a few things:
People are interested in literary history — not in a passive video course or lecture way, but in a way that lets them be part of the story and walk through history.
There’s a gap in literary history tour offerings in the city (I know of only one or two other companies that offer literary tours). Like I say, if I found a gap in the Boston tourism market, I’m going to take advantage of it!
I really like doing this. Creating, planning, researching, and running a tour is work. But it’s very fun to share my literary history knowledge with folks who are interested in it, connect with new people every week, show them around, and see their “aha!” moments (I LOVE the “aha” moments, when I can see history coming out of the textbook and into their world!).
Ink & Cobblestones quickly became my flagship and is still filling every weekend. But it wasn’t going to be my only tour, and the idea for a Harvard Square literary history tour soon came to mind…
