A Weekend in…Woodstock
Our favorite businesses in our favorite towns.
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First things first: the Village of Woodstock is not where Woodstock, the music festival, took place. If you’re looking to see the grounds where it all went down, you need to go to Bethel Woods, which is about 60 miles away. If you’re looking to experience peace, love, and good vibes, the Village of Woodstock offers that and more. Woodstock has been a thriving mecca for artists, musicians, spiritual seekers, nature lovers, and tourists for years. On Sundays the village green fills with bongos and djembes and tie dye. Lava lamps, granola, and utopian ideals live on. It’s lovingling referred to as “the most famous small town in the world.” A bit of an exaggeration perhaps, but it is iconcic. One of the defining moments in its history is when it was “discovered” by artists. In the early 1900s the Byrdcliffe Colony, Maverick Colony and the Arts Students League put down roots at the base of Overlook Mountain. From then on it has attracted artists of all kinds and people from all walks of life looking for something a little different.
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Stay at the Woodstock Way. Accommodations are perfect: upscale, modern, and convenient. Enjoy waking to the sounds of the Tannery Brook Waterfall that cuts through town and borders the hotel. We recommend a pastry and coffee from one of our favorites, Bread Alone. But if bagels are more your thing check out The Mud Club. The important thing to note here is that you can’t go wrong. For lunch we like Tinker Taco, Sharkie’s, or a sandwich from Woodstock Meats. For an afternoon pastry, try Caffe. Sylvia is a favorite for food and atmosphere. Another great option is Good Night, which offers delicious South East Asian cuisine in a lively setting. We recommend finishing things up at Early Terrible.
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Stay at The Herwood Inn, which pays homage to stars like Aretha Franklin and Stevie Nicks. And what’s more rocking than being able to bring along your pooch (w/out extra fees! woohoo!)? Fun, colorful and bound to inspire, you probably don’t need to do much else but bring your harmonica and chill on the porch. After a disco nap, you have several options for live music: Bearsville Theater is alive and well after a major renovation and restoration in 2022. You can’t truly understand the history of Woodstock and the role music and the arts have played in the community without a trip to the Bearsville Theater. Colony is another venue that offers a range of live music and events. If you’re brave and there on a Monday, you can even be part of the show & open mic it. Your trip is not complete without stopping by The Woodstock Music Shop and if you can, visit on April 22nd for Record Store Day. Did we mention drum circles are Sunday? Not to be missed & wear your dancing shoes.
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Stay at Graham & Co. Though not technically in Woodstock, it’s close enough. Phoenicia is about a 20 minute drive to the heart of the village. You can lounge by the pool, mingle with neighbors and enjoy the grounds of this very cool, affordable, fun hotel. You’ll be even closer to these trails, tubing in the Esopus, or Rail Explorers. For a more low-key nature walk, check out the Comeau. A moderate hike, try Overlook Mountain. You may want to see Opus 40 or The Big Deep. For some nature-inspired souvenirs and momentos, check out Lovewild, Maverick Road, and Mirabai.
