A Weekend in Woodstock, NY

Having never been anywhere in upstate New York, I jumped at the chance to accompany my friend on a getaway birthday celebration. A mere two-hour bus ride at about 25 bucks each was just too good of an opportunity to pass up, so I packed a bag and headed to Woodstock.

The first thing you notice upon arriving in Woodstock is, and I mean this with the utmost respect, the cuteness. The bus dropped of us on Tinker Street–sort of the main drag–in front of darling boutiques, cafes, bookshops, and bakeries where the cuteness is met with a laid back, simple vibe that is instantly enjoyable.

Before exploring Tinker Street, we walked to the charming bed and breakfast my friend booked for the weekend. We passed Waterfall Way–appropriately titled as the serene sound of rushing water from a small waterfall surrounds you for a good portion of the walk–and arrived at the Woodstock Inn on the Millstream after about five minutes. Our room was small and cozy with two twin beds, a large closet, a flat screen tv, and a quaint 1940s-esc bathroom compete with a large shower and a few of my favorite Aveda products.

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Our next stop was Tinker Street where we explored the various shops selling everything from handmade jewelry to organic hand cream. A standout amongst the shops was The Golden Bookstore.  It was incredibly well stocked with current and classic literature, and is the kind of place you could spend hours exploring. It also has that great “book smell” which might sound odd, but it’s a smell that reminds me of the library in my elementary school and I just love it.

Here are a few more must-visit shops in Woodstock:

I was surprised to find that the majority of the food in Woodstock is organic, locally sourced, and most importantly, absolutely delicious. We happily ate A LOT during our stay. Here are a few of our new favorite spots:

Joshua’s. Skip “The Smorgasbord” appetizer of humus , falafel, and other Mediterranean dips and go for the Moussaka -hands down the best I’ve ever had–the Shamatov Chicken, Baby Kale and Arugula Salad, and the Stuffed Artichoke. All SO good.

Shindig. Fantastic cocktails. We particularly loved the Ginger Mule! We shared a lamb burger, Brussel sprouts, and onion rings with sriracha aioli. So good I can’t even.

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For something sweet, you MUST go to Peace, Love, and Cupcakes (You can’t miss it, there’s a big pink sign that says CUPCAKES!) We picked a double chocolate cupcake that was voted THE BEST CUPCAKE IN THE COUNTRY by the Food Network!!! It was divine, but even better was the extremely unassuming Vegan Chocolate Banana cupcake.

I know what you’re thinking because I was thinking the SAME THING, but for reasons I cannot fully comprehend, it was the best damn cupcake I’ve ever had in my whole life. Ever. It was everything a cupcake should be–fluffy, moist, and INCREDIBLY flavorful–but not too sweet. I’m still in awe. Go there, get the cupcake. Hell, get both. We did.

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Places we did not go but really want to check out next time include:

Later that night we went to see a Billy Joel cover band at the Bearsville Theater–a place the bar tender calls “the coolest place in town.” We thought this was bias talking but to be frank, it’s really the only place to “go out” in town.

That’s part of Woodstock’s charm. The entire community comes out and everyone hangs together. Families with kids, as well as young people, older people, couples, singles, and tourists all gathered to listen as the local school showcased some of Woodstock’s young talent before Gene Ween hit the stage.

Everyone was buzzing about the event set to happen the following night, in which the whole town would come together for a fundraiser for a local teacher who was recently diagnosed with leukemia. Everywhere we went the next day, people asked us if we were going to the benefit and it truly warmed my heart to see a community that is so connected.

Though most of the action seems to happen at the Bearsville Theater, Wok and Roll also features live music and inexpensive drinks.  Just about a mile down the road, Wok and Roll is a casual bar with cheap drinks, blue and purple lights (because, Woodstock), and some of the best local musicians Woodstock has to offer.

Fun Facts About Woodstock:

The next day, we visited Karma Triyana Dharmachakra, a beautiful monastery in the mountains. Then we walked the three or so miles back into town where we discovered a Drum Circle was about to take place. After watching for a while we ate lunch, and caught a bus back to the city.

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Overall it was a wonderful experience. Woodstock is not a glamorous place. Almost everywhere you go is casual, but that is part of its rock ‘n roll charm. People there tend to be unfussy and kind, and the community is just that, a community, where people sit on benches in the center of town, sipping coffee, and chatting. It’s a beautiful place where yoga, healthy food, relaxation, meditation, music, and FUN are valued above flashy cars, trendy fashion, and corporate coffee shops.

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I highly recommend checking it out! If you do, I would love to know what you think and where you went! Let me know in the comments or on Twitter @missvranhalen

Follow along on Instagram for more pics @nicolevranjican 

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2 thoughts on “A Weekend in Woodstock, NY

  1. HI! This is Janice from Peace, Love and Cupcakes! Thanks so much for your kind words! I’m so glad you enjoyed the cupcakes!. Hope you’ll come back and visit soon! 🙂


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