It just must be something about the name “Woodstock” that determines that this town is going to be worth checking out. From Woodstock, Vermont’s postcard-perfect New England street scenes to Woodstock, New York’s counterculture vibe, all of these Woodstocks should be on your itinerary this season.
Woodstock, Vermont
This Vermont town is often lauded as quintessential New England, with a bustling downtown with stately historic homes, plentiful dining options, and boutiques galore. Starting with the iconic FH Gillingham general store, spend an afternoon browsing. Just north of town, the Saskadena Six Ski Area is perfect for hitting the slopes. Billings Farm is where history and agriculture meet. Stop at Sugarbush Farm for homemade maple syrup and cheese. Grab a drink at the tavern in the Woodstock Inn or a burger and a Vermont beer at Worthy Burger.
Woodstock, New York
Known for the nearby festival that bears its name, this Woodstock has one foot still in 1969 and one in the present. It’s not just the fact that the town is (understandably) stuck in the classic rock era. It’s listening to Radio Woodstock while you’re driving on the Levon Helm Memorial Highway. Park the car and start exploring. Each of the many souvenir shops has memorabilia galore, from clothes to posters of all your favorite 60s and 70s era bands, but that doesn’t fully influence the vibe. It’s like streaming music doesn’t exist. It’s the real hippies who still call the town home. An afternoon in Woodstock will be a bit slower-paced than everywhere else. Enjoy lunch at Oriole 9 or cupcakes at the award-winning Peace, Love and Cupcakes.
Woodstock, Connecticut
The least well-known of the bunch, this rural Connecticut Woodstock includes an outpost of the craft beer behemoth, Tree House Brewing Company. Woodstock is an autumnal playground for all senses; pick apples at Woodstock Orchards, shop for antiques at the Scranton Shops, or grab lunch at a cafe. Route 169, which is certainly one of New England’s great roads, bisects this town. In any season, though, Woodstock has so much to offer. Visit the Roseland Cottage, meander on walking trails, or if you’re in town during Labor Day weekend, attend the Woodstock Fair.
Woodstock, New Hampshire
In the heart of New Hampshire’s White Mountains is Woodstock. With plenty to do outside, including the Lost River Gorge, it also has a cute downtown anchored by the Woodstock Inn and Brewery. This restaurant and inn provides a comfortable, family-friendly atmosphere with a range of beers. Wander in and out of general stores, stop for an ice cream or a brew at Twin Barns, and make sure to scale the rocks at Cascade Park. If cabin-dwelling is on your New Hampshire bucket list, plenty of accommodations will serve your needs in town.
In the northeast, these four Woodstocks should be on this year’s travel itinerary. Each offers something unique, such as New Hampshire’s hiking trails, Connecticut’s leaf-peeping spectacular, and New York’s far-out ethos.
