In my young adult years, a few friends and I often ventured upstate to Woodstock, a historic rustic landscape surrounded by the Utopian vistas of the Catskill Mountains. Located little more than two hours by Adirondack Trailways outside of New York City, this hamlet has a reputation for being a hippie, artsy, spiritually-minded place populated by many a Manhattan transplant. Curious to see what new things had sprung up and what treasures remained, I decided to revisit my grizzled, groovy roots over a long weekend.
I pre-booked a small room at The Woodstock Inn by the Millstream (48 Tannery Brook Rd, 800.420.4707, woodstock-inn-ny.com), and found it centrally located right off the main strip. The room itself was tidy and quaint, with two twin beds that ran me $106 per night. The next morning, I awoke to wafting buttermilk aromas that could only come from a freshly made country breakfast.
After some small talk with the owner, I was handed a map of the town and pointed in the direction of the Byrdcliffe Arts and Crafts Colony, 34 Tinker St, 845.679.2079, woodstockguild.org) founded in 1903. At Byrdcliffe, one will find a theater, aikido dojo, pottery studio and countless quirky cabins. The scenery is studded with sculptures, rock formations, bright colored birds, gardens, and artists milling about. Walking tours are conducted regularly during the summer, and a map is available online for those who want to explore on their own. After dabbling with arts and crafts, I made my way back to the Byrdcliffe Theater where the Fringe Festival was underway, complete with paid and free performances.
Back through the center of town, I passed Barack Obama signs and a massive flea market, the Mower’s Saturday Market (Maple Lane, 845.679.6744), which is open every Saturday and Sunday through November. Farther down Tinker Street, I saw life in perennial motion: innumerable yard sales and boutiques like Pondicherry (12 Tinker St, 845.679.2926, pondi.biz) full of crocheted wall hangings and hand-loomed hammocks, rare books, tie-dye shirts and well-preserved antiques from a hippie heritage. Yoga mat-strapped women filed into the eco-friendly Bliss Yoga Center (6 Deming St, 845.679.8700, blissyogacenter.com) while a few families paid their respects at the Woodstock Cemetery, which is divided between “regular folk” and “artists.”
I sat at the Garden Cafe on the Green (6 Old Forge Rd, 845.679.3600), a gourmet vegetarian restaurant in the town’s central park, and watched a 20-person drum circle begin chanting “Bar-ack-Oba-ma! Bar-ack-Oba-ma!” a mantra to match the political sentiments of Woodstock. My next stop was the Karma Triyana Dharmachakra (335 Meads Mountain Rd, 845.679.5906, kagyu.org/ktd), a Tibetan Buddhist Monastery where the Dalai Lama has occasionally visited. So it goes, the holy place is in the middle of a huge expansion, which when complete, will offer hostel-style lodging for travelers interested in learning about Tibetan Buddhism. The rates around completion are expected to be about $30 per day. Free guided tours are available Saturdays and Sundays, as well as periodically scheduled free meditation instruction.
Located directly across from the monastery is the entrance to the trail for Overlook Mountain. If you’re not a hiking enthusiast—and even if you are—don’t underestimate the difficulty of this 2.5 mile steep hill climb. I made it to the top about 30 minutes before sunset, and was rewarded by the beautiful, haunting ruins of the former Overlook Mountain House and the majestic Catskill mountain range.
I returned down the trail as night crept into the sky, and without a flashlight (not advised) returned to my room to get ready for dinner. I decided to explore a restaurant about three miles from the town center. A hip neighborhood spot, The Red Onion (1654 Route 212, Saugerties, NY, 845.679.1223, redonionrestaurant.com) is known for its delectable daily specials, fresh squeezed juices, succulent bites of seafood and house-made pasta dishes that pair well with their extensive wine list.
The beet salad and basil ravioli with lamb sausage were superb, and the lemon poppyseed cake gave just the right punch of lemon and moist sweetness. In the aftermath of slightly hitting on the bartender who’s birthday it was (and whose boyfriend I eventually discovered was nearby) I was invited to her birthday party, which would be full of some of the most amiable, attractive, and hippy people I had ever met. Although the place was not devoid of small-town attitude, the majority of folk there, as in town and throughout Woodstock, was welcoming to the foreigner.
The next and final day, I experimented with yoga, swam in the stream by the Inn, and indulged in a raved-about massage at River Rock Health Spa (Has since closed). I continued my boutique, gallery, and occasional bar hopping in town, and caught a movie on the origins of LSD during the Woodstock Film Festival. If you are willing to exercise a bit of patience, everything is in walking distance. Native New Yorkers who often feel trapped by the experience of having to drive once outside the city will find this trip immensely refreshing.
If you have chosen to bring a bicycle or rent a hybrid car, I recommend venturing out of town to savor steak frites at New World Home Cooking (1411 Route 212, Saugerties, NY, 845.246.0900, ricorlando.com) or to meet the three legged goat at the Woodstock Farm Animal Sanctuary (35 Van Wagner Road, Willow, NY, 845.679.5955, woodstockfas.org).
A few of the last real remaining hippies in Woodstock are, of course, old now, with long flowing gray hair that drapes over their tie-dyed ensemble. I talked with them about the ’60s and how much of Woodstock had changed with the new set of status-seeking and material-minded residents. Gone are the days of free love and easy money. Compassion has been exchanged for self-promotion and although the “tune-in and drop-out” philosophy remains, it is more escapist than transcendental. If you want to get in touch with your inner-hippie, and live amongst a fading breed, try entering your comfort zone in a place time nor the Grateful Dead would want you to forget.
How to get there:
Take Adirondack Trailways from Port Authority, which will drop you off at the village green. To get to the Woodstock Inn, take the first left after the village green onto Tannery Brook Lane (Joshua’s Restaurant is on the left corner), head over a small bridge and before the T, you will see The Woodstock Inn on the right side. Bicycles are allowed on Adirondack Trailways and will make exploring and getting around much easier, but there are some baggage rules to take note of. Other alternatives include taking an Amtrak train to the Rhinecliff Station, which is about a 15 mile cab ride to Woodstock. Finally, refer to our hybrid car rental guide for eco-friendly car options.
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Sarah Knapp is a Brooklyn based entrepreneur whose love for the outdoors and community building led her to the October 2013 creation of OutdoorFest. She has a BA in History, is a Wilderness First Responder and a NY state hiking, camp and boating guide. Her proudest achievement to date is reading the Aeneid in Latin. 
Allison was one of our first top writers and Chief Editor but is no longer working with offMetro. Allison is a native New Yorker, who has lived in Rome, Tuscany, Melbourne, Toronto and Los Angeles. She frequently contributed travel pieces to Family Travel Forum, using her own children as guinea pigs as they travel the globe. She never missed a chance to sample local delicacies, as her love for travel goes hand-in-hand with her love for food and wine. 
Josh Laskin is a freelance travel writer and photographer based in the White Mountains of New Hampshire. When he is not at work or on the road, you can find him in the mountains snowboarding, climbing, hiking, fly fishing, mountain biking, and eating bagel bites.
Annie is a travel writer, environmentalist, and surfer based in Venice, CA. She heads up our West Coast team, keeps our grammatical errors in check, and makes sure our California writers always have a plan for their next adventure. Follow Annie’s travels @annelisemcb.
Carly Pifer is a freelance writer who has been known to follow whims inspired by romantic movie scenes or colorful street style shots to India, Japan, Tunisia and Argentina. After stints living in Seoul, Boston, Paris and Los Angeles, writing and searching for something intangible, she landed somewhat steadily in Brooklyn and has begun to find inspiration in her more immediate surroundings. 
Kate E. O’Hara is a New York based freelance writer and photographer who loves all things food—especially the people who make it and market it. Her writing aims to capture the essence of the food experience; the stories that go well beyond a plate of ingredients. In addition to her love of food, Kate is also known to have a hankering for red wine and craft beer. You can also find Kate on Instagram