Welcome to Woodstock: A Tranquil Oasis In Upstate New York
Photo Credit: Photo Credit: Tim Kitchen

Photo Credit: Photo Credit: Tim Kitchen

Welcome to Woodstock: A Tranquil Oasis In Upstate New York

New York , wide open spaces
Spencer Jones
Spencer Jones May 11, 2023

New York City rejects sleep like a toddler, while Woodstock can barely keep its eyes open.

This bucolic town is just two hours or so from the city, but they’re a world apart. If you’re looking to escape the honking horns and frantic energy, Woodstock is the perfect oasis. From the moment you arrive, you’ll want to inhale as much fresh air as possible. As the foliage sheds its fall colors for summer’s arrival, how can you not feel at peace?

Hop in your Subaru 2024 Crosstrek, blast your favorite playlist, and set aside a few days for another, quieter side of New York. Don’t drive? No problem. Book an Amtrak ticket, and get off at the Rhinecliff station.

In Some Ways, Woodstock Never Left The 1960s

Photo Credit: Ralph Ackerman

Older generations recall the Woodstock Festival of 1969, where sex, drugs and rock and roll were up front and center. But the festival actually took place in Bethel – about an hour and a half from Woodstock. Organizers decided that “Bethel Festival,” didn’t have the same zing, and the rest is history.

As a town, Woodstock happily honors that 1960s nostalgia. Tie-dye shirts and kitschy items are displayed in shop windows. There are nods to Dylan, Hendrix, and other music titans. In the spirit of “Free Love” and respect, locals are mannerly. Drivers yield, and they won’t honk if you need extra time to cross the street. This may seem inconsequential, but it’s nice to know that courtesy isn’t totally out of style.

Where Should You Stay In Woodstock?

Photo Credit: Spencer Jones

Sure, the major hotel chains are convenient, but they lack warmth. A standout example of a boutique accommodation is Woodstock Way Hotel. Check in at The Tannery, which functions as a lobby and communal space. Sit by the waterfall with a good book. The fire pits are a romantic touch, especially when the temperature dips at night. You aren’t supposed to swim in the brook, but it’s tempting on a scorching day.

Take your pick from a variety of standard rooms, suites and residences. They’re characterized by bohemian-chic accents and wood facades. The genius of the design is how the buildings harmonize with nature. At night, the sound of rushing water lulls you to sleep, and birdsong greets you in the morning.

Rest, Go On An Adventure, or Both – It’s Your Choice

Photo Credit: Spencer Jones

Woodstock Way is in the middle of town, so can access quite a few shops and restaurants on foot. Close to it is Café Espresso. This was a magnet for popular performers over the years. Upstairs is The White Room, where a young Bob Dylan retreated to write his music. Sometimes, Johnny Cash, Joan Baez and his other contemporaries joined him. You’ll see Dylan’s white typewriter, along with boxes of old matches and half-smoked cigarettes. Even if you aren’t a fan, you get to engage with a piece of music history.

Once you’ve had a chance to freshen up, head to Silvia for top-tier American cuisine. That isn’t an exaggeration. The wood smoked pork chop, chicken schnitzel, and mushroom lentil pâté are impressive, not to mention the decadent desserts. Good luck choosing what to eat, unless you have the good fortune to sample the whole menu.

Set aside an evening for Early Terrible. As with Woodstock Way, this bar incorporates nature in its design. It looks like it’s built into the trees, and the interiors feature antique windows, plank ceilings, and Chesterfield leather sofas with just the right amount of wear. The music enhances the moody vibe; think deep house and dark pop. You can opt for beer or wine, but the craft cocktails are works of art. For a spicy kick, try the jalapeño margarita. If you’d rather play it safe, go with the classics, like a Manhattan or an Old Fashioned.

You might hesitate leaving Woodstock, because who wants to return to stress? Add on another day or two if you can- you owe it to yourself.

Harold & Belle's

Travel Noire, Food, Cooking, Savor