Viewers gathered in Windsor last summer to watch “One Town at a Time,” a documentary about the 251 club of Vermont. Photo courtesy of Mike Leonard

The new executive director of the 251 Club of Vermont wants to attract more families and young people to one of the state’s quirkier organizations.

“I just fell in love with it,” said Stephanie Young of the club, whose goal is for members to visit all 251 towns, cities and gores in the state. “I would talk about it all the time.”

Young, who lives with her husband and two young sons in Burlington and joined last summer, learned of the opening for a new director through the club’s newsletter. 

She knows she has some big shoes to fill.

Sandy Levesque of Bethel had been at the helm for 10 years, and as only the fifth executive director in the club’s 65-year history, she is credited with professionalizing the organization and growing membership.

Just last year, the club gained several hundred more members. In all, Levesque estimates there are more than 6,000, although membership is by household so that number is not exact. 

During her tenure, Levesque helped bring the club online and sought partnerships with Cabot Creamery and other businesses to promote membership. She also started a newsletter, which highlights members and their stories.

Levesque says the club incorporates a good mix of freedom and structure for people interested in exploring the state. 

“I call it a lawless organization,” Levesque said. “We have no rules, so you can take on this goal and do it in a couple of weeks or you can do it in a lifetime. You don’t have to report to anyone when you finish, it’s all on the honor system.”

The club’s president, George Hooker of Rutland, said this has allowed members to put different spins on the challenge.

“Some people will make sure they bicycle in every town, some people will make sure they put their canoe in a waterway in every town,” he said. “One woman wants to visit every cemetery, so she’s taking the cemetery approach. Some people want to have a cup of coffee in every town.”

Hooker, who joined the club six years ago, has completed about 60% of the challenge. He said he appreciates the club for bringing attention to — and celebrating — every corner of Vermont. 

“Some of the things that you find when you get to these places, it’s just amazing,” he said. “Fabulous coffee shop, fabulous bakeries, unique histories, famous people, famous events that occured, unique architecture. There’s something about every place.”

Young began in her new role on Jan. 1 and plans to expand outreach efforts onto social media in the hopes of attracting more young people and those who might be new to the state. She also wants to provide resources and suggested itineraries for different demographics, including busy parents. 

“I have a lot of friends with kids the same age as my kids, and a lot of times they feel like they don’t have time to join the 251 Club,” she said.

Mike Leonard holds up his 251 Club membership card. Photo courtesy of Mike Leonard

However, Young said her family has used the 251 Club as a way to see new things and spend time together, and she believes other families could do the same. 

She also wants to update the website and give people the ability to pay for membership and merchandise online with a credit card — currently the only way to purchase anything from the club is by mailing in a check. 

“What we’re really looking forward to is expanding our demographics to include more younger people, to make it more of a family friendly thing,” Hooker said. “We’re hopeful that will take us in a slightly different direction and expand our horizons.”

The 251 Club board also recently welcomed two new members, each of whom has a unique relationship to the organization and ideas about how to promote it. One new board member, Jessamyn West of Randolph, first learned about the club when she moved to Vermont in the 1990s. West is currently completing her 251 quest for the second time, now with the added goal of visiting each of the state’s 183 public libraries. A librarian by training, West said that she loves libraries and towns for similar reasons. 

“One of the reasons I love libraries is because they belong to the public, and one of the reasons I love towns is because they are occupied by the public,” she said. “Just that idea of the spaces that belong to everyone, it just kind of makes me happy. I like that you can just walk around a town.” 

While making the “One Town at a Time” documentary last year, Mike Leonard revisited many of the places he first traveled to in 2006 and caught up with some of the same people 12 years later. Photo courtesy of Mike Leonard

West’s fellow new board member, Mike Leonard, grew up in Woodstock and completed his 251 challenge with two friends in the summer of 2006 between semesters at college. 

“Joining the club and taking on this challenge was really a reaction to being in New York and feeling conflicted about my identity,” he said. “That summer was our opportunity to reckon with that feeling and learn more about where we call home.”

This past summer, Leonard released a documentary about the club, and his youthful experiences traveling around the state, called “One Town at a Time.” In the film, he combined old camcorder footage from his original journey with new footage he captured 12 years later when he revisited many of the same places. 

In both completing the challenge and making the movie, Leonard said his big takeaway was that the strong community values he grew up with exist across the state. 

“Honestly, I don’t think that’s something that exists everywhere in the country,” said Leonard, who lives in Vermont while enrolled in a graduate program in New Hampshire. “I think ultimately that’s why the 251 Club has been able to exist for so long, and so successfully, and why there’s such a draw to it.” 

He also acknowledged that being from Vermont gave him the ability to engage with locals — both in 2006 and 2018. 

“I think the fact that I’m a Vermonter gives me a certain key to access conversations with other Vermonters,” he said, “The whole joke is that you have to be a ninth generation Vermonter to actually be considered a Vermonter, that kind of thing. And I think the fact that I am that automatically gives me some unwarranted credibility to have these sorts of conversations with people, and they’re more willing to open up.”

After premiering the movie in Woodstock, Leonard has held more than 30 screenings last year. As a new board member for the organization, Leonard hopes that “Vermonters and Vermontophiles,” as he put it, take the time to see new parts of the state. Although he did not complete the challenge a second time when finishing filming for the movie, he said he was once again left with the feeling that each town in Vermont has something unique to offer. 

“There are a lot of swathes of the United States that are the same sort of suburban ‘sameness’ that you might have outside of Tampa or outside of Cleveland or outside of Austin,” he said. “I really think that Vermont is different. You could argue that about everywhere, of course, but I really think that the community minded values of Vermonters is one thing that really makes us special, and makes the 251 Club worth doing.”

Viewers gathered on Church Street in Burlington last summer to watch “One Town at a Time,” a documentary about the 251 Club. Photo courtesy of Mike Leonard

Sarah Asch is an intern for VTDigger covering Burlington and Chittenden County. She recently graduated from Middlebury College where she studied English literature. Previously, she has worked at the Addison...