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While New York and Vermont are not exactly similar, a town in both states bears a similar name. The name of these two towns is Woodstock. When the name “Woodstock” is mentioned, many travelers scratch their heads, wondering which of the two is exactly meant. And while other travelers know for a fact that there are two towns that go by the same name, they can be hard-pressed to pinpoint the difference between the twin towns with respect to how they look or any distinctive character they exude.


In this article, we pull the curtain aside—to reveal the differing looks of these two towns. We’re going to see whether they are two sides of the same coin or two sides of different coins. Let’s dive in.

Here’s What To Know About Woodstock, Vermont

Woodstock, Vermont, has long been noted for its extraordinary elegance, bucolic look, and princely ambiance. That’s the reason many of the state’s wealthiest call it home. When properly examined, Woodstock, Vermont, is a resort village with an upscale look—exuding class, grace, and finesse.

The village scenes are time-frozen as if revealing glimpses of halcyon days. When we come to it, it’s no exaggeration that only a few New England villages come close to Woodstock for its idyllic look. If these descriptions seem peppered or a little hyped up, the words of Senator Jacob Collamer, a one-time confidant of President Lincoln—should dispel any lingering doubts. Here’s what he said of Woodstock, Vermont: "The good people of Woodstock have less incentive than others to yearn for heaven." Well, the reason should be obvious. They were already in heaven.

Yet Woodstock Vermont isn’t just about its heavenly look. It’s rich in history and boasts several historical sites and museums. The town itself is aged. It was chartered in 1761, more than a decade before Jefferson’s Declaration of Independence. For history buffs, Woodstock, Vermont, is home to the very first ski tow in the United States that went into operation in 1934. In January of that memorable year on the pasture hill of a farm owned by a man called Clinton Gilbert, an endless-rope tow, powered by a Model “T” Ford engine, hauled skiers uphill for the very first time. This occurrence would eventually usher in a new dawn in winter sports.

For other historical sites, a drive on the town’s peaceful backroads will reveal a quiet, historic piece of Woodstock culture dotted with such consequential edifices as the Calvin Coolidge Memorial Homestead and the Old Constitution House. And while Woodstock, Vermont has many museums, according to Tripadvisor, the award-winning Billings Farm & Museum is ranked first by travelers.

Related: Why You Should Opt For A Small Town Getaway Right Now, Over Anywhere Else.

Here’s What To Know About Woodstock, New York

Many relate Woodstock, New York, to the 1969 world-famous music festival that also bore the same name. However, the truth is that the music festival was actually held in a different town in another county, even if such legends as Bob Dyland did the planning work in Woodstock, New York. Still, that alone doesn’t rob Woodstock New York of its shine or sheen. For starters, Woodstock, New York, is one of eight unique hidden gems to see in upstate New York. And again, the fact that Woodstock, New York is set in the stunning backdrop of the Catskills tells something about its breathtaking beauty. Just like its Vermont counterpart, there’s no denying that this New York town is elegant, charming, and picturesque.

However, even if Woodstock New York is charming and elegant, it’s charm and elegance are of a slightly different tone and texture. While we would not deny that it’s quaint and laid-back, this town has a hippie vibe that’s more pronounced than its Vermont counterpart. Maybe the roots of this hippie vibe can be traced to the 1969 music festival. But that can’t be true since the area’s music actually predates 1969. Whatever the cause, this charming small town has a vibe and rhythm that’s discernibly hippie—even if not that loud.

Related: 10 Small Towns In America That Should Be On Your Travel Bucket List.

Today, this charming town showcases its art personality through the presence of several art galleries (especially on Tinker Street), the Woodstock Artists Association and Museum, and the Woodstock Byrdcliffe Guild—where visitors can take art classes as well. And while both these towns are small, Woodstock, Vermont, has less than half the population of Woodstock, New York. Also, while New York’s Woodstock still looks classy, it doesn’t come close to the upscale look of her Vermont namesake.

Here's the parting shot. While both these two towns are charming and scenic through and through—their charm, rhythm, and vibe—are discernibly different.