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The Tale Wood Of Two Stocks

About three and half hours apart lie two getaway destinations that share a name— Woodstock—each with its own distinctive history and personality. Woodstock, New York, which rests among the rolling hills of the Hudson River Valley, has an unpretentious atmosphere and laidback appeal. Woodstock, Vermont, nestled among the Green Mountains, is a quintessential New England town with a scene reminiscent of simpler days.


Mention the name Woodstock and what may be the most famous rock concert ever held immediately comes to mind. In mid-August of 1969, more than 400,000 young people descended on The Woodstock Music and Arts Fair. Although the three-day event was officially held on a farm in Bethel, New York, some 50 miles from Woodstock, the namesake village remains synonymous with peace, love, and rock-and-roll.

Today, New York’s Woodstock is sprinkled with well- heeled day trippers and vacation home owners. The town center is a pleasant place to spend the day, complete with benches, shade trees, and some of the best people watching you’ll find anywhere. During warm weather months, this “colony of the arts” provides outdoor music, a drum circle in the Village Green, and other events catering to locals and tourists alike.

Driving into Woodstock, the relaxed yet lively vibe is seen and felt. Here, a modern homage to the 1960s counterculture revolution lives on. If you stay long enough, you may spy a Volkswagen bus decorated with a peace symbol. Throughout town you will find colorful wooden painted signs and an eclectic array of shops brimming with everything from tie-dyed tees, handmade jewelry, candles, and incense, to fashionable casual apparel. There’s a Tibetan Buddhist Monastery that serves as a retreat and study center, and Bearsville Theater, a popular venue with no bad seat in the house, which hosts musicians and other artists. Theatre, music, and events also abound at the Woodstock Playhouse.

The picturesque, walkable town includes an assortment of art galleries and cafés. If you’re interested in well- prepared New American cuisine, killer cocktails, and good fun, make a dinner reservation at The Red Onion Restaurant & Bar, located in an historic pre-1850 farmhouse just three miles east of town.

Woodstock, New York offers unique accommodations, such as The Enchanted Manor, an eco-friendly, spa-style B&B that focuses on health and wellness. For a luxe lodging experience in the Catskills, the historic, award- winning Mohonk Mountain House luxury spa and resort is roughly 35 minutes away. The Emerson Resort & Spa in Mt. Tremper is another nearby upscale lodging option. It lays claim to having the largest kaleidoscope in the country.


A true embodiment of a peaceful New England village, Woodstock, Vermont has been named the most beautiful town in the United States by Condé Nast Traveler. Complemented by centuries of history and featuring a covered bridge close to downtown, strolling the streets is like stepping back to a bygone era. A handwritten chalkboard in the middle of town, labeled the Town Crier, indicates upcoming events and festivities. Numerous small shops, boutiques, and restaurants fill the downtown area. Many visitors also enjoy meandering along the side streets and looking at all the old, immaculately kept houses, especially when they are decorated for the autumn season.

Take a scenic walk from the town center to Billings Farm & Museum. Regarded as one of the finest outdoor history museums in the country, it combines a fully-operating Jersey dairy farm with educational exhibits and interactive programs and events. If you want to get up close to eagles, hawks, owls, and other raptors, visit the VINS Nature Center, just 15 minutes from Woodstock. This well-maintained sanctuary rescues, treats, and rehabilitates injured birds, but the raptors that live there permanently are the main attraction. Since their past injuries make it impossible for them to survive in the wild, they remain at VINS where visitors get to meet them. Or perhaps you might fancy a short hike up Mount Tom that offers a stunning view of Woodstock from the summit? The trail begins on Mountain Avenue behind the covered bridge, and the hike takes you just 30 minutes from town.

Local artisans are plentiful in and around Woodstock, Vermont. For instance, Farmhouse Pottery has been designing and crafting pottery, housewares, and accessories for more than a decade. Bookworms will find a well-curated selection at the Yankee Bookshop. And be sure to stop by Woodstock Farmers’ Market, a haven for foodies stocked with fresh produce, staples, prepared foods, and Vermont-made cheeses, chocolates, jams, breads, and more.

B&Bs and privately-owned hotels are plentiful in and around both towns. In Vermont, The Woodstock Inn & Resort offers a classic New England resort experience that evokes a timeless elegance. Guestrooms are decorated with Vermont original artwork and include cozy hand- dyed blankets. The breakfasts are hearty, and the spa is divine. If you’re a golfer, check out their unlimited golf package. Other lodging options include the newer, family- friendly 506 On The River. The river view penthouse suite even comes with a private patio with rocking chairs.

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