I had always dreamed of going to Woodstock. When I’d dreamt it, I saw late nights and live music, locking eyes with a band member, falling in love with this band member, going on tour, and inevitably coming back to Woodstock open an artisanal candle shop, or something of the sort. So, when we got Woodstock Way Hotel on the One Night app, I was determined to tell its story.
To say the least it didn’t take me long to get out from between my sheets and behind my laptop to turn my Woodstock dream into a reality. The premise of the story? To take you lovely readers on a journey with me through Woodstock by foot. Using Woodstock Way as a base for my hopelessly romantic journey, I would spend my 24-hours there without a car, only able to explore my nature-filled surroundings in my fancy city shoes.
I did not embark on my journey Upstate alone, along for the ride to be my unsolicited wing-woman and walking partner was Sophie. You may remember the Dutch-American actress from our time at the Gramercy Park Hotel, but if you don’t, she’s known as an international woman of mystery— who lucky for me happened to also be single. Anyways, back to the beginning, our arrival at Woodstock Way.
Amidst a flowing waterfall, the modern wooden structures that comprise the trendy boutique seem to blend in with the surrounding forest. We frolicked around and entered through the boho-chic lobby where we were given keys to a King Waterfall Suite, and yes, the digs were as royal as they sounded. The open-plan room was adorned in work from local artists, a gorgeous king-sized bed, curated vinyl collection and turntable, and most importantly, a private outdoor balcony with water rushing beneath us.
Once we’d had a glass of rosé and did the always necessary photoshoot pre-destroying the room, we were ready to head out and take on the town. Woodstock Way is conveniently located just steps away from the town center. We wandered aimlessly, stopping to admire understated passers-by and quaint storefronts as we were pulled towards our first destination, the Garden Café. It’s the exact type of place I imagine when I say I would love to open a small restaurant somewhere. The Garden Café appears intentionally worn-down, brightened by beams of natural light, and serves insanely delicious vegan food. Let me spare you the judgment and let you know that I’m not vegan, the food was actually just that good. We’re talking mouth-watering black bean quesadillas, chickpea blinis, and our second glass of wine and bloody mary of the day.
A few sips in we decided it would be fun to download Tinder and see if there were any eligible bachelors to be found in Woodstock. Not my ideal way to meet my musician, but hey, work with what you got. We sat side-by-side and swiped left on many men with mom tattoos and tractors—nothing against either, just not my thing. We swipe right on a select few and put our phones away, our matches would have to wait until the evening because we had some shopping to do before everything closed for the day. Like an old-time movie montage, we make a stop into the town’s best-known vintage clothing store, Three Turtle Doves, and pair the most absurd of outfits together. We spend far too long and bought many an unnecessary accessory (pearls, oversized shades, a golden belt), before jaunting to Pacama, a sleek and upscale handcrafted furniture studio where we gawked at local artisans.
Back in our King Waterfall Suite, Sophie and I slip into something slightly more appropriate (only slightly) and dance to our Woodstock-inspired vinyl collection. The dancing continues through the brisk spring night as we made our way to dinner at Silvia’s. Now Silvia’s is Woodstock’s most formal restaurant, and definitely the most happening eatery in town. The crowd was filled with casually cool couples of all sexual preferences, elders, millennials, real-life foodies, and seemingly every subsection of culture. However no matter which way you slice it or what you came for, the restaurant is downright romantic. It’s dimly lit, has dark green velvet seats, is filled with sultry art, and we snagged a corner table and took ourselves on a date.
And boy, we were expensive dates. Sophie and I ordered—and finished—shishito peppers, halloumi cheese, Korean BBQ lettuce wraps (definitely the highlight), roasted duck, and duck fat potatoes. Yes, for two. Yes, the waiter was confused. Once we had licked our plates clean Sophie threw me an ‘I’m in a major food coma and if we don’t get up now I’ll have to go home’ look. So a few minutes later, we waddled our way across the street to Early Terribles, a bar we’d overheard was the trendy new spot in town.
On the outside, Early Terribles appears as a nondescript wooden shack, on the inside, it is all of my interior design fantasies come true. Cozy fireplaces, couches, wooden sculptures, and bohemian art surround a horseshoe-shaped bar tended to by a chatty mixologist from Bogota who previously spent twenty years in Queens and is now a full-time Woodstock resident. To put it simply, he was a pure delight. We get to talking about how he traded busy city life for Woodstock’s peaceful, musical way of life and booming bar and restaurant scene. And then he gives us a free round of shots. This would ultimately lead to our downfall.
As last-call came, our last shot had given us a shot of energy, and our new mixologist friend advised us to walk ten minutes across town to Station Bar & Curio. Let me remind you, we’re both already at least 8 drinks deep. We arrive at the buzzy bar housed in an old station house, apparently known for serving 100% Hudson Valley products, and immediately caused a scene. Sophie, upon opening the door, accidentally kicked a dog. The cardinal sin. Everyone in the whole place turned silent, stopped what they were doing, and darted evil eyes at us the two silly city girls who I repeat—NOT ON PURPOSE—hurt an adorable pup. After getting over their glares, the crowd could be described as young and grungy people ‘too cool’ for city life, and we were perfectly into it.
Down the hall, we find a pool room and insert ourselves into a game. Unsurprisingly in my current state, I could barely even hit the ball. The kind gentlemen who let me play found it endearing. I found it entirely embarrassing. In the corner, Sophie meets a young suitor wearing a very on-brand beanie. While he was cute on the outside, honestly, it seemed like he hadn’t talked to a girl in at least six months. Cute face, though. He could definitely be cast as the beaux on Pretty Little Liars. It had reminded me of my select right-swipes on Tinder, but just as I picked up my phone to find a potential suitor for myself, it died. I’ll never know what could’ve happened with my Tinder missed connections, but just like that, I was ready to call it a night.
The very next day we arose to birds chirping and the sound of water flowing, and for a second, I felt fresh as ever. That was, however, until I sat up. There was zero chance Sophie was getting out of bed to fetch hangover reinforcements, so I took the duty upon myself. Getting anywhere in Woodstock by foot had proved easy thus far, however, my hangover-induced sluggishness meant making it five steps into town, all the more difficult. Shades on and hoodie up, I find my way to The Mud Club, known for their Montreal-style wood-fired bagels and killer coffee. I get two everything bagels, an almond croissant, and a dark chocolate walnut cookie to help ease the pain.
After breakfast in bed and a long washing in the room’s oversized walk-in shower, we were ready for one last walk. I don’t know who we thought we were kidding, but we decided we could muster up the energy to hike up to the abandoned hotel at Overlook Mountain. It was a chilling two-hour journey to the ruins, uphill the entire time, but when we got to the top, all of our aches, pains, and worries went away. We perched ourselves on a rock 3,140 feet over Woodstock, and peered through ruins of a once luxury hotel.
24-hours later, we’d officially done it—we’d conquered Woodstock by foot. While I didn’t meet my grungy band member to whisk me away on tour, I’d hopelessly fell in love with Woodstock and my home here, Woodstock Way. My feet were tired, but my heart was full and mind was clear. We all need a recluse from the noise of New York City, and in my short time in Woodstock, with its open people, fresh air, starry skies, live music, and charming local businesses, I found an escape and inevitably, a second home.