Population 811: When Your Main Street Is Actually Just a Trail

There's something deliciously Vermont about Greensboro—a town so small that its "downtown" consists of basically one general store and a post office, yet somehow manages to attract beer pilgrims from around the globe. Highland Lodge, a historic Northeast Kingdom B&B overlooking Caspian Lake, offers 136 acres to explore in Vermont's culture-rich and unspoiled landscape, which is basically Vermont-speak for "we have more land than people, and we're proud of it."

With just 811 residents spread across 38 square miles, Greensboro has achieved the remarkable feat of being less dense than a small parking lot while maintaining the audacity to subdivide itself into eight different "places"—including glamorous locales like Campbell's Corners and East Greensboro. It's the geographic equivalent of naming every closet in your house a different neighborhood.

A Founding Father Who Literally Ghosted His Own Town

The town's origin story reads like a 18th-century version of someone buying a timeshare they never visit. Named after Timothy Green, who received the original charter in 1781, Greensboro was essentially founded by a guy who took one look at the deed, promptly let his land get sold for unpaid taxes, and never bothered showing up. Talk about commitment issues.

Of the original proprietors, only three actually decided to live there—apparently even in colonial times, people took one look at the remote Vermont wilderness and said, "Thanks, but I'll pass." Timothy Green basically invented the art of ghosting two centuries before the term existed.

The Highland Lodge: Where Rich Summer People Rough It

Near the shore of Caspian Lake in Vermont's Northeast Kingdom, the Highland Lodge originated as a family farmhouse in the 1860s. Developers, planning to build more than 70 cabins on the grounds, bought the abode in 1926. Today, this "rustic" retreat features no A/C, just mountain breeze to preserve the simple, laid-back charm of Vermont lodge life, though our elevated location and cool mountain climate make for breezy nights and comfortable days.

The lodge has perfected the art of convincing wealthy visitors that paying premium prices to sleep without air conditioning constitutes "authentic Vermont living." My husband's family has been staying at the Lodge for 30+ years, proving that some people will return annually to the same place for decades just to feel like they're roughing it—when the biggest hardship is deciding between the French toast or berry crumble at breakfast.

Hill Farmstead: The Brewery That Made Isolation Fashionable

But Greensboro's true claim to fame is Hill Farmstead Brewery, the revival and continuation of 220 years of Hill heritage and handcrafted history in North Greensboro, Vermont, where Shaun returned from Denmark in 2009 and founded Hill Farmstead Brewery in 2010 on his family's ancestral land. In 2011, Hill Farmstead was awarded the title of 'Best New Brewery in the World' by consumer review website RateBeer.com.

This remote brewery has achieved the impossible: convincing craft beer enthusiasts that a 70-mile drive through actual cow pastures to wait in line for $25 beer is a spiritual experience. The history of the Hill family includes the founding of Greensboro and North Greensboro, the building of its first roads, mills, and its first tavern in 1809—meaning they've literally been getting people drunk in this exact spot for over 200 years.

The brewery operates on a simple principle: make outstanding beer in the middle of nowhere, and people will come. And come they do, turning this tiny Vermont hamlet into a mecca for beer nerds who use words like "terroir" with a straight face while standing in what is essentially a fancy barn.

Caspian Lake: Not Actually the Caspian Sea

Let's talk about Caspian Lake—the body of water that Greensboro residents discuss as if it's the Mediterranean. Named after the world's largest lake (because apparently Vermont has never met a grandiose comparison it didn't like), this "pristine" lake serves as the backdrop for Highland Lodge's longest private beach on pristine Lake Caspian.

The lake offers all the charm of a New England summer retreat: cold water, occasional loons, and the persistent feeling that you're paying resort prices for what is essentially a very expensive camping experience. But hey, at least you can tell people back home that you vacationed on the shores of "Caspian"—just don't mention which one.

Greensboro, Vermont, is the perfect encapsulation of rural New England: a place where 811 people live spread across enough land to house a small city, where the biggest attraction requires a pilgrimage through dirt roads, and where a pond gets named after the world's largest lake because why settle for accurate when you can aim for aspirational?

Think we were too nice to Greensboro? Head over to RoastMyTown.com to see the full roast and discover what other small towns are getting the treatment they deserve.