Vermont's Four-Season Destination Is A Town Bursting With Cozy New England Charm And A Cute Swimming Hole

Quaint New England towns tend to get all the attention during the fall season, when the colorful foliage is in full bloom and pumpkin spice lattes are on the menu. But if you're craving those cozy vibes at any other time of the year, look no further than the tiny town of Dorset, Vermont. Chartered in 1761 — 30 years before Vermont became the union's 14th state — Dorset is brimming with history, charm, and plenty of things to do.

Thanks to its scenic mountain views, stretching farmlands, and stunning valleys, it's a beautiful place to visit regardless of what season finds you in the southern Vermont burg. Those vacationing in the summer months, however, will have the opportunity to appreciate some of Dorset's more famous destinations and attractions, from a unique swimming hole with a fascinating history to a revered performing arts festival.

Tucked into the state's breathtaking Green Mountain and Finger Lakes region, Dorset sits about an hour east of Saratoga Springs, New York. As such, the Albany International Airport is your best bet if flying in from outside New England. The other major, albeit much smaller, option is the Rutland Southern Vermont Regional Airport, just 20 miles from the town. If you're an out-of-towner looking to tack Dorset onto a larger Boston trip, a flight from Logan International Airport to Rutland will do the trick, putting you in the air for just over an hour.

If you're planning a trip to southern Vermont, you'll definitely want to carve out some time to visit the Dorset Marble Quarry. Doubling as one of the country's best swimming holes and a fascinating historical site, the quarry is a must-see — and must-swim — if you're in Dorset during May through September. Established in 1785, the commercial quarry was the country's first, providing materials to the likes of the New York Public Library and the Montreal Museum of Fine Arts. At 120 yards long, 30 yards wide, and up to 60 feet deep, the watering hole is a paradise for swimmers, sunbathers, and those just looking for the perfect picnicking spot.

Even if you're not looking to cool off in the chilly water — which only reaches about 50 degrees Fahrenheit on a hot day — the quarry is a sightseeing destination you won't want to miss. Sporting beautiful blue-green water, breathtaking ledges and walls made of marble, and an intoxicating peek at a manmade structure reclaimed by nature, the favorite local spot is massive, majestic, and best appreciated in person. It's typically open during the summer months, from 9 a.m. till dusk, but if you're looking for the most up-to-date info, the quarry also maintains a Facebook page with hours, updates, events, and more.

After a long, lazy day at the swimming hole, visitors can take in some world-class entertainment at the Dorset Playhouse. Running for nearly 50 years, the theatre's renowned summer festival puts on both classic and original productions, many of which have gone on to become acclaimed Broadway and off-Broadway productions.

While both the Dorset Marble Quarry and Dorset Theater Festival deserve spots at the top of your itinerary, there's plenty more to keep you busy in the charming hills of southern Vermont. For starters, there's no shortage of outdoor adventures to author for fans of walking, hiking, and mountain biking. Of course, the northern East Coast is well known for its incredible ski resorts, and winter sports lovers can slide down some of that famous powder just 20 minutes from Dorset — at Bromley Mountain Ski Resort.

If shopping is more your speed, the town center has you covered and then some with a fantastic selection of designer boutiques and artisan retailers. Dorset also puts you just under an hour away from the state's oldest flea and farmer's market in Newfane. But let's talk about what really matters — food! The town's brimming with farm-to-table eateries, chill cafes, and prime spots to just sit and enjoy a craft cocktail or beer. In fact, if you want to begin your day with an oven-baked goodie and cap it with a local craft adult beverage, we suggest making the Dorset Union Store a regular stop. The town also offers a variety of lodging options, from hotels and bed and breakfasts to historic inns, including Vermont's oldest, The Dorset Inn, which began welcoming guests in 1796.