Millennial Takes Downtown-Wooster Helm

Thomas Breen photoWhen Caroline Smith first moved to New Haven from Lexington, Kentucky, she would never have defined herself by her relationship to a city.

Seven years later, Smith has become nearly synonymous with the city she proudly calls home. The energy, enthusiasm, ambition, and kindness that she brings to each of her community-building endeavors have made her a familiar face to residents throughout New Haven.

“I never thought about cities as an entity that you could form identity around until New Haven,” Smith told the Independent during a recent interview at Whole G Cafe on Orange Street. Smith, 24, first moved to New Haven to attend Yale as an undergraduate, and is now the the co-director of marketing at the local tech start-up SeeClickFix.

“But when I came here, I fell in love with the people, with this city, and, for lack of a better phrase, I built stakes.”

Smith’s local “stakes” have dug that much deeper now that she has been elected chair of the executive board of the Downtown-Wooster Square Community Management Team (DWSCMT). Her neighbors elected her to the position last week during their monthly meeting on the second floor of City Hall.

Replacing outgoing chair Peter Webster, Smith, who has served as the DWSCMT’s treasurer for the past 12 months, will be responsible for shaping the agenda and priorities of one of the more active and efficient community management teams in town.

This new position is just the latest community investment for a woman who is representative of a young generation of local activists and entrepreneurs who straddle the town-gown divide. They are actively trying to dissolve that sense of difference so that people on both sides can recognize shared obstacles, interests, and networks of support as neighbors and fellow citizens of New Haven. 

From Kentucky to Yale to SeeClickFix

Lucy Gellman photoSmith grew up in Lexington, the daughter of two psychology professors. As she notes in Our City: A Little Book about New Haven, a collection of 12 blog posts about contemporary life in the Elm City that she recently published, Smith comes from a family of immigrants: her mother is Korean, her father the child of British immigrants.

She gravitated towards psychology at Yale, studying what influences and motivates people towards action, and threw herself into extracurriculars, getting her first exposure to New Haven outside of Yale through student government and frequent jogs throughout the city.

Smith first met SeeClickFix founder Ben Berkowitz her sophomore year of college as the two volunteered during a snowstorm to help shovel clear paths for snowed-in locals. By the time she graduated from Yale in 2014, she was eager to work at a company founded and based out of New Haven, and quickly got a job at the Chapel Street start up.

“I think the biggest myth about New Haven is that brilliance can’t come from neighborhoods outside Yale,” she said. “That’s the biggest myth that I see, and that’s a perception that I want to see change.”

As the co-director of marketing for SeeClickFix, Smith travels throughout the city and the country, highlighting stories of citizens and governments working in big and small ways to improve their communities, from fixing potholes to addressing major public health issues.

One of her next presentations will be for the Newhallville Youth Ambassadors program, where she’ll be teaching local teens how to use SeeClickFix, and then will be walking around the neighborhood with them and reporting on everything from toppled street signs to overflowing trash cans.

“The most exciting thing in the world is to be able to build things everyday with the people that you love,” she said. “That’s amazing that New Haven gives you the capacity to do that.”

Bike Equity and Bike Justice

Thomas Breen photoIn 2015, Smith co-founded New Haven Bike Month, an annual celebration of biking culture in New Haven that focuses on equitable access to biking resources for all neighborhoods.

“What started as something that built off of the wave of biking culture in this city has really narrowed in on bicycle equity and bicycle justice,” Smith said. “How can we ensure that residents of every single neighborhood feel safe and inspired to ride on bikes? How can we promote bicycle justice through neighborhood empowerment?”

In addition to a handful of group rides and biking info sessions, this year’s New Haven Bike Month saw “Open Streets” events in Newhallville, Fair Haven, the Hill, and Downtown. Bike mechanics from the Devil’s Gear Bike Shop and the Bradley Street Bicycle Co-op offered free tune ups and repairs; Bike Month volunteers painted pop-up bike lanes and gave out dozens of free helmets; and locals revelled in bike-centric performances like a wheelie competition at Criscuolo Park and gravity-defying tricks by professional stunt rider and Westville resident Mike Steidley. 

For Smith, “bicycle justice” comes down to celebrating the different ways that biking happens in different neighborhoods in this city, while also providing resources and support for as many people as possible to feel like they too can ride their bikes in New Haven. The key to all of Bike Month’s programming is bringing people from different neighborhoods together to share their interests, skills, experience, and expertise so that the community as a whole can benefit from the experience.


Lucy Gellman photoAbout a year and a half ago, Smith co-founded another New Haven organization bent on building community through shared difference: Collaboratory.

An event series that brought together Yale and New Haven-affiliated organizations into the same room to discuss their missions and three challenges that were preventing them from realizing those missions, Collaboratory provided a space for town and gown participants to talk openly about what problems faced the city today and how they as students, neighbors, and entrepreneurs might go about trying to solve them.

The first two organizations that participated were the Yale College Council and the Whalley-Edgewood-Beaver Hills community management team and, eight sessions in, Smith is now looking to turn Collaboratory into a support group for local residents looking to start small businesses.

“There were a lot of brilliant individuals in the room for Collaboratory, but maybe the word ‘entrepreneur’ did not seem accessible to them,” Smith said. “We’re now looking to turn Collaboratory into a small business start up incubator for New Haven residents, so that, when a New Haven resident wants to start a business, they have a place to go. We want to build a structure so that entrepreneurship is accessible to people throughout this city.”

As one of the New Haven organizations that will receive funding through CTNext’s Innovation Places 2017 grant, Collaboratory is looking to kick off its next phase as a local start up incubator this upcoming Fall. 

Building Stakes

Thomas Breen photoOn Tuesday night last week at the DWSCMT meeting at City Hall, Smith’s first order of business upon being elected chair of the team’s executive board was to ask the members present about how they could best reach out to people not already involved.

How could the team’s composition best reflect the diverse populations of downtown and Wooster Square? How could the team best empower all residents to feel that they too have stakes in supporting their neighbors and their community?

Xia Feng from the New Haven Free Public Library suggested that members each bring a friend to the next meeting. City Hall staffer Michael Harris proposed setting up a welcome table at the Wooster Square Farmer’s Market. Smith wrote down each suggestion, adding doorknocking, posters, and meetings with local business owners to the list.

“I do know that people fight for what they love,” Smith said a day later, reflecting on what it takes to turn residents into community activists. “The question is, how do you get people to fall in love with a city? How do you make them fall in love with its people? How do you create spaces where people can become friends and build stake in each other, and be able to connect in a variety of ways?”

For Smith, that love for her city and her neighbors is visible in every ventures she undertakes, and her brief time in New Haven to date offers a model for how passionate, determined individuals can bring people together by first laying down their own stakes.

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posted by: Timothy G. ORourke Jr. on June 29, 2017  1:05pm

A very nice story and needed respite from the most recent news.  To try to answer her questions, just think of the moral of It’s a Wonderful Life and think what the city would be like without people like her.  Just keep going on…

posted by: Kevin McCarthy on June 29, 2017  1:11pm

Given the number of places I see her, I firmly believe that Caroline has an identical twin sister in town.

posted by: BetweenTwoRocks on June 29, 2017  2:28pm

Congratulations to the set of Caroline Smith clones that are slowly marching towards inevitable Mayordom. I’ll be happy to say I knew one of her clones way back when.

posted by: Jonathan Hopkins on June 30, 2017  9:59am

Woohoo! Congrats to a much deserved appointment. Great shirt!

posted by: Anonymous Bosh on July 5, 2017  12:43pm

She’s got *my* vote!