The Ultimate Vermont Road Trip

Chairlift Q & A

One summer in college, Mike Leonard and two high school friends decided to join the “251 Club” and visit each of  Vermont’s 251 towns. In 2018, he did it again and this time made a movie about it.

In 1954 poet and historian Dr. Arthur W. Peach put out a challenge in  his column in Vermont Life for “the native born and those born elsewhere but with Vermont in them to discover the secret and lovely places that main roads do not reveal.” To do so, he suggested a visit to all the towns in the state. Since then, more than 6,000 have officially joined what is now called “The 251 Club.” They include former governor Jim Douglas and cartoonist Ed Koren. The rules are self-governing: some stop at a post office, others have run or biked to every town, one couple put a canoe in a pond in each town. In 2006, Woodstock native Mike Leonard spent a summer visiting all 251 towns. In 2018, he revisited many to make a documentary about the club. The film “One Town at a Time,” premieres this summer and has screenings scheduled around the state. See

Are you a Vermonter and how did you hear about the Club?

Three out of my four grandparents are native Vermonters (the Leonard name goes back nine generations in Pomfret) and my dad’s parents joined the club when they retired, driving around the state in an RV.

What inspired you to join?

When I left for college at New York University I started to grapple with my identity. I began bragging about being a Vermonter then realized I was a bit of a phony and remembered the 251 Club. I spent the summer of 2006, after my sophomore year, driving around the state in a ’91 Ford Escort beater car with the music up and the windows down and camping out. Two high school friends, Sam Avant and Julia Norcross joined me. That summer was our chance to explore our identity: At the age of 20 you’re trying to figure out your place in the world.

Where do you live now?

I’ve been studying nursing at University of New Hampshire and living in West Fairlee but my husband—he’s from Northern Ireland—and I are moving to Montpelier. It’s tough driving 20 miles to a  general store.

Hardest place to get to?

Lewis, in the far northeast corner of the state, used to be notoriously difficult to get to as the dirt roads were only open certain times a year.

What were you favorite places?

Lake Willoughby is an almost other-worldly sight, with the mountains framing the lake in a majestic way. Bennington County has one of the most remote places in the state, Glastonbury. It’s one of the five unincorporated towns in Vermont (places with populations that are not large enough for a local government) and it’s more wilderness than anything. I love hiking the Long Trail from Glastonbury up to Stratton. Somerset Reservoir is also idyllic and even more isolated than Willoughby—it takes some real commitment to get to. And I love taking my canoe out on Woodward Reservoir in  Plymouth.

Did you visit many ski areas?

I  ski raced in high school at Suicide Six and  I’ve always loved ski areas in the offseason and the trails you can hike up. There’s a different feel there in the summer that I’ve never been able to pinpoint. It feels like you have the place to yourself. It’s what attracts Vermonters to Vermont.

Favorite town?

I love any town with a general store and people sitting outside on the porch and chatting. That’s something we do well in our state.

Biggest change since 2006?

So many general stores are closing. These were places where people would gather and get to know one another and that’s special. That’s how we overcome differences, by talking to each other. In Vermont, that happens at the general store.

Lisa Lynn

Editor of VT SKI + RIDE and Vermont Sports.

One thought on “The Ultimate Vermont Road Trip

Comments are closed.