Vermont's Most Overlooked Town: A Deep Dive into Wheelock's Spectacular Mediocrity

Picture this: you're driving through Vermont, expecting maple syrup farms and charming covered bridges, when suddenly you stumble upon Wheelock—a town so forgettable that even GPS seems surprised it exists. In 2020, the town had a population of 759 people, spread across 39.8 square miles, making it less populated than most shopping malls on Black Friday.

But here's the plot twist that would make M. Night Shyamalan jealous: this sleepy Vermont hamlet has one of the most incredible educational benefits in America—and almost nobody uses it.

The World's Most Underutilized Scholarship Program

Here's where Wheelock gets genuinely fascinating (yes, that sentence exists). For more than a century Dartmouth College has been making good on a promise to students from a hardscrabble Vermont town that helped the keep the school afloat in its early years: get in, and your tuition is free. But in that time only nine students from the town of Wheelock have taken advantage of the offer of a tuition-free Ivy League education.

Let that sink in. Dartmouth College—where this year's tuition is $48,120—offers free education to any Wheelock resident who can get admitted. The scholarship exists because in 1785, the Vermont Legislature granted Dartmouth 23,000 acres of land in a town it named Wheelock, after Dartmouth founder Eleazar Wheelock, and in its early years the college helped support itself with money from rent and goods the town produced.

It's unclear how the free tuition offer came to be, but the legend is that it happened during the 1830s when then-Dartmouth President Nathan Lord was in Wheelock collecting rent. He is believed to have quipped "Anytime anybody wants to go to Dartmouth, send him down."

So why have only nine people used this golden ticket in over a century? Simple: Fewer than 10 Wheelock children graduate from high school every spring. Your town's biggest claim to fame is also its biggest self-own.

A Town So Small, Everyone Knows Everyone (Unfortunately)

The population density was 15.7 people per square mile—which means you have better odds of running into a moose than a neighbor. With a median household income of $72,143, Wheelock residents are doing okay financially, assuming they don't mind driving 30 minutes to find a decent coffee shop.

The town's demographics tell a story of Vermont at its most Vermont-esque: 92.0% White followed by Other (6.5%) and Two or More (0.9%). The ancestries read like a European history textbook, with French (22.1%), English (21.6%), Irish (18.7%), German (9.2%), Scottish (7.4%), French Canadian (4.0%).

But here's what's really telling: Length of stay since moving in significantly above state average. Translation: once you're in Wheelock, you're apparently staying forever—whether by choice or because you forgot where you put your car keys.

Geographic "Highlights" and Tourist "Attractions"

Let's talk about Wheelock Mountain, with an elevation of 2,782 feet. In most states, this would be called a hill that someone got ambitious about naming. But in Vermont, where expectations run as low as the elevation, it's apparently worth bragging about.

Wheelock has an interesting and involved history. In 1774 it was patented by New York as part of a much larger tract named Bamf to a group of Scots who planned to divide the whole tract into two towns, Bamf and Sterling, after their old homes in Scotland. Yes, this town was almost named Bamf, which would have been infinitely cooler and probably attracted at least three more tourists annually.

The town layout reveals Vermont's commitment to making things complicated: Wheelock is located in northwestern Caledonia County and is bordered by the town of Sheffield to the north, Sutton to the northeast, Lyndon to the east, Danville to the south, Stannard to the southwest, and Greensboro to the west. That's six neighboring towns, most of which you've also never heard of.

The Modern Reality of Rural Vermont Living

Today's Wheelock operates with Millers Run School (PreK–8), located at 3249 Vermont Route 122, serving local elementary and middle school students. For grades 9–12, students are given a choice of public or approved independent high schools in surrounding communities through Vermont's school choice system.

For visitors exploring the Northeast Kingdom, Wheelock represents the kind of small, quiet town that appears on maps but offers little in the way of tourist infrastructure. Its significance lies in its unusual history rather than developed attractions, and in the landscape itself — the wooded hills, dirt roads, and scattered ponds that characterize much of rural Vermont at its least commercial.

The town's practical realities include reliance on well water and septic systems, winter maintenance of unpaved roads, limited broadband access in many areas, and the necessity of traveling to surrounding towns for most services. So basically, it's like camping, but you pay property taxes.

The Verdict: Vermont's Best-Kept Secret (For Good Reason)

Wheelock, Vermont represents something uniquely American: a place so unremarkable it becomes remarkable, so forgotten it becomes unforgettable, and so small it somehow contains one of the country's most generous educational benefits. It's a town where the biggest news is probably when someone's cow gets loose, but where getting into Dartmouth means hitting the lottery jackpot—if you can manage to stay awake through high school.

Wheelock is thus the only town in Vermont ever to have been chartered to an organization wholly outside of the state. As late as the mid-l800's the rentals paid by Wheelock tenants continued to provide a large percentage of the permanent funds for Dartmouth College.

In a world of Instagram-famous destinations and overtourism, maybe there's something refreshing about a place that doesn't try to be anything other than what it is: authentically, unapologetically, beautifully boring.

Think we were too nice to Wheelock? See the full, unfiltered roast cards and discover what locals really think about their hometown on RoastMyTown.com. Because sometimes the truth hurts—but it's also hilarious.