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Southern Vermont

Spotlight map of Southern Vermont region

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Tichnor Brothers postcard of Bennington's Battle Monument

There’s so much in Southern Vermont that it’s hard to know where to begin. From the busy little towns on the Connecticut River to breathtakingly bucolic hills along the New York border, and ski towns in between, the region offers everything you could want from Vermont.

The towns along the Connecticut river change in and out from sleepy countryside to bustling towns. Starting with Brattleboro in the southeast, you’ll find a small urban arts community, funky and fiercely independent. Stroll around downtown and visit the shops and galleries, then grab an espresso and people watch. 

Further north is Bellows Falls in the town of Rockingham, whose history is tied to the Connecticut River with the opening of the Bellows Falls canal in 1802 whose locks allowed shipping to bypass the Great Falls. Later, the canal provided power to mills, and even later, in the early 20th century it was widened to power turbines to generate electricity. Visit the fish ladder, a marvel of construction, check out the early Native American petroglyphs south of the Vilas Bridge, and stroll the historic downtown.

Cut inland to the west to visit the pretty town of Grafton, the beneficiary of the Windham Foundation established in 1963 by New York City financier Dean Mathey. The Foundation has done an amazing job of preserving and protecting the character of the town, and it’s hard to decide which season it looks best in. Picture perfect. Stroll around and be sure to stop in at the Grafton Village Store, 200 years old and going strong. For a real treat, both from an antique and culinary perspective, dine at the 1801 Tavern and bed overnight at the Grafton Inn.

Northward from Grafton is Chester, with its amazing Victorian homes, tiny row of shops, and the hauntingly beautiful Brookside Cemetery. Chester is also the place for antiquing, and be sure to stop in the Stone Village Historic District and stroll around to admire the snecked ashlar (I love saying that) stone buildings. 

Heading west over to Weston, you’ll find the king of Vermont’s general stores, aptly named The Vermont Country Store. It’s gotten to be quite a tourist magnet, so the crowds can be quite dense in the fall. Make sure you also give due credit to the Weston Village Store across the street, which predates the Vermont Country Store by a lot. Fudge, cheese, maple syrup, a whole room of jigsaw puzzles are just some of what it has to offer. And for icing on the cake, visit the adjacent Christmas shop. While you’re in town, check out the Old Mill Museum and catch a performance at the award-winning Weston Theater Company Playhouse.

It should be mentioned here that there are numerous general stores throughout Southern Vermont – some favorites include H.N. Williams General Store in Dorset, J. J. Hapgood General Store in Peru, and the West Townshend Country Store.

Over to the western side of the region, tucked between the Taconic and Green Mountains is the beautiful town of Dorset. Spend some time wandering around and admiring the ubiquitous white clapboard against breathtaking mountain views. Be sure to check out the marble quarry too – long since shut down, it was the first marble quarry in the nation, and its marble can be found in the New York Public Library, Montreal Museum of Fine Arts, and Brown University’s Library, just for starters. Today, the quarry is pristine, thanks to its private owners, and a very popular swimming hole – 60 feet deep!

South of Dorset is Manchester, with somewhat of a split personality. The historic Main Street is, like Dorset, a pretty clapboard community dominated by the Equinox Resort. This is an excellent place to stay, or dine or order a drink to enjoy on a porch rocker. The American Museum of Fly Fishing is just north, and the Orvis Flagship Store is across from that, complete with indoor Fish Pond. Dogs are welcome and many come to visit with their owners. Hildene, the estate of Robert Todd Lincoln, is to the south, and is very worth a visit, both for the estate’s beauty and its history. 

Manchester Center, on the other hand, is an incorporated village in the northern part of the town, but a “village” it is not. Rather it is a shopping mecca of designer outlets. If you’re in Vermont, and want to really get your shopping game on, this is the place. 

Traveling south from Manchester on through Sunderland, Arlington and Shaftsbury, the amazing views just never stop. It’s very worth detouring off on side roads to get even more visual candy, most particularly up the Mount Equinox Skyline Drive. 

Landing in historic Bennington, visit the Bennington Battle Monument, from the top of which you can view three states. The nearby Bennington Museum is an art museum that holds the world’s largest collection of Grandma Moses paintings along with historic and artistic items from the area. This is all in the picturesque Old Bennington Historic District. Heading east from there, stroll the Downtown Historic District, with its shops and eateries.

Southern Vermont has an abundance of ski resorts, including Bromley Mountain in Peru, Stratton Mountain, Magic Mountain in Londonderry, and Mount Snow in Dover. Snowshoeing, cross-country skiing and snowmobiling can be found, of course, throughout the region, along with innumerable hiking trails. Enjoy river tubing and splashing in the many local swimming holes.

Are you sold yet on Southern Vermont? I’ll see you there!

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