From the Boston Book Festival: ‘Boston in 100 Words’ Writing Contest Makes Authors of Us All


Capturing a slice of Bostonian life in only one hundred words is a difficult task, but “Boston in 100 Words” contestants boldly embrace the challenge. On Saturday, Oct. 29, past winners of the contest, current judges, and the contest’s lead organizer Jane De León Griffin joined local Boston residents at the Boston Book Festival to present a panel discussing topics ranging from the creative process of tackling 100 word-vignettes to building community through storytelling. Winners of the contest will have their stories transformed into illustrations by local artists that will be displayed on digital screens throughout downtown Boston and on over a thousand posters throughout the MBTA system.

Among the panelists was Louis Frank, an ESL and music teacher as well as the first place winning author in 2020. With his 100 words, titled “Freedom Trail,” Frank tells the story of a friend visiting Boston who thought she had walked the Freedom Trail, but in reality defined her own path, passing stores with Spanish names, camped cop cars, and Fenway Park.

“As a teacher, I had taken students on field trips to the official Freedom Trail,” said Frank. “I thought the irony of [my friend] Julie mistaking the Freedom Trail for the actual path [that she took] to be really sweet.”

“The reason I was so happy to see [this] story win first place in our first ever contest was because we're hoping that these stories are, in a way, like an inside joke that only people who know the city really well would understand,” said De León Griffin. “If you don't know that Julie didn't really walk the Freedom Trail, then Louis's story doesn't have the same impact. But for those of us that hear all those places, we know that that's not the real trail. That's what makes the story beautiful; the Freedom Trail doesn't have to just be that red brick line that all the tourists follow, it can be whatever you make it.”


Past successful stories also took on more retrospective tones. Tristen Grannum, the 2021 honorable mention winning author, wrote a story inspired by his childhood experience. His 100 words capture how a game of cricket in Franklin Park reminds him of his parents’ upbringing.

“My parents immigrated to the United States in the 1970s, and they basically built a life in Boston,” said Grannum. “One of the things that helped connect them to home was cricket; my father played cricket and a lot of people that we got to know in the Boston community played. It was that and [reggae played on the radio] that really kept them grounded in the culture and identity of the Caribbean.”

Later, Shirley Jones Luke, an English teacher at Boston Public Schools and one of this year’s judges, shared what she tells her students when teaching storytelling: Everything is worth writing about, and no story is too insignificant.

“How your family navigated Covid, how the pandemic affected you, your schooling, and how we're trying to recover: Those are stories in the now that you can write about that are fresh,” said Jones Luke. “You want to capture those memories.”

She also discussed how this advice relates to how she will go about judging this year’s submissions: “You'd be surprised at, when you put something in the world, who it might connect with, who might resonate with your work. As a judge for ‘Boston in 100 Words,’ I'm looking for that connection from the person who, in their 100 words or less, makes an immediate impact.”

Theresa Okokon, another judge for this year’s contest, shared similar sentiments on the nature of what constitutes a story. As someone who teaches nonfiction, essay, and op-ed writing, she finds herself constantly telling her students that “what is happening to you matters and is interesting.”

In reference to the details included in past winners’ stories, from street names to radio stations, Okokon said, “those tiny little mentions are so small, but so sticky and important; you can create a whole 100 word world around this little thing that sticks with you.”

Although the panel only featured winners of the general category (i.e. contestants over the age of 17), “Boston in 100 Words” accepts stories from writers of all ages. In fact, the contest seeks to amplify the voices of people who might not consider themselves artistically or authorially-inclined. Afterall, as Okokon said, “storytelling is the art of performing about your own life.” Indeed, each contestant’s 100 words of Boston come uniquely from their own eyes and lived experiences.

This year will be the third annual contest. The deadline to submit to ‘Boston in 100 Word’s’ third annual contest is Dec. 17th. The submission page can be found here.

—Staff writer Karen Z. Song can be reached at