Settled On The Connecticut River Is A Funky New England Escape With Indie Shops, Jazz, And Famed Ski Jump

While populous, big-name New England states like Massachusetts tend to get all the attention — home to nearly 7 million New Englanders out of 15 million total – verdant and quirky Vermont (population: 626,000) embodies some of the best that the region has to offer. From Manchester with its romantic cafes and road trips through the Green Mountain State's countless majestic waterfalls to multi-season hikes through the conservation-minded Marsh-Billings-Rockefeller National Historical Park, Vermont isn't only a skiing paradise, not by far. And now we can add one more village to the mix of shoulder-to-shoulder, walkable, and red-brick downtowns, one that happens to abut a babbling river and has an annual ski jump competition: Brattleboro.

With modern roots going back to 1724, Brattleboro was actually the first English settlement in what became Vermont, which was never a colony but an independent republic founded in 1777. A standout town in many ways, like being the site of one of the U.S.' first psychiatric facilities in 1834 and Vermont's first public library in 1837, Brattleboro has always had one foot firmly in the arts and one pointed forward. 

This history ripples to the present and can be felt in the fabric of the town, its independent shops, music and theatre venues, numerous art centers, including a jazz center, and its exceptionally cozy tavern, Kipling's Tavern, named after once-resident and famed author Rudyard Kipling, who wrote "The Jungle Book" while living in neighboring Dummerston. Brattleboro is located approximately one hour north of the nearest mid-sized city, Springfield, Massachusetts, and it is well worth the visit, whether for a short-term or long-term stay.

Brattleboro is just a joy to walk around and explore. Its old, red-brick downtown area near the Connecticut River — particularly the bit near the intersection of Elliot Street and Main Street — is exceptionally picturesque and worth the visit. If you can snag parking at a nearby lot, you can duck into an inordinate amount of cool, independent art shops, book shops, antique shops, thrift shops, a record store, a theater, and a museum all packed into a mere 15-minute walk, total. 

The staggeringly reviewed Book Lovers sits on this route (5.0 out of over 100 Google reviews), as does the small, charming Lost Time Books. The latter sits next to the historically-minded (not just kitsch-minded) Twice Upon a Time antique store, which sits next to Boomerang, an artsy and vintage-focused clothing store, which sits next to another antique store, Distinctive Decor, which is just across the street from Vermont Artisan Design, which focuses on glassware and even has a gallery of purchasable paintings. This round-up should give you an idea of what it's like to visit Brattleboro. And, it doesn't even take into account the gamut of cafes and bars on the same streets, the most notable of which is the aforementioned Kipling's Tavern, with its stupendously comfortable, dark wood, and point-lit interior.

And because art and music reign in Brattleboro, we have to mention the Vermont Jazz Center south of downtown. It offers jazz workshops for learners, festivals, jam sessions, and a suite of faculty who teach there either year-round or during its core summer educational programs. It doesn't have a hugely full calendar of performances, but if you time your visit right, you can still see one.

Because we're talking about Vermont, we can't get away with not talking about skiing in some way. No matter how charming, artsy, or folksy, Brattleboro's arguably biggest annual event and notable feature is its Harris Hill Ski Jump. It takes place in February every year, and just to show you that this isn't some fad, it recently celebrated its 100-year anniversary. It also recently rebuilt its staircase for spectators, which now stands 209 steps tall. 

The jump itself is exactly what you'd expect. Skiers go to the top of a slope, ski down, fly off the end, get scored for the jump, and the winner takes home a trophy as judged by five judges. But far from being a small, local event, the Harris Hill Ski Jump Competition is an international spectacle that attracts skiers from all over the U.S. and even Europe. The jump is the only 90-meter (about 300 feet) jump in New England, and meets Olympic and International Ski Federation (FIS) standards. And for those who can't attend in person, the entire event will be broadcast on the Brattleboro Community TV YouTube channel.

And while visitors to Brattleboro, and Vermont at large, may not be careening down an icy slope come February, travelers can still ski nearby if they want. Brattleboro Ski Hill is right in town, and Ski Maple Valley is a short way north. For everyone else, Vermont in the wintertime is a beautiful, snow-covered treat to visit. Take care while walking around slushy, shoveled sidewalks, and you'll be able to enjoy a whole other seasonal facet of Brattleboro.