Travel Guide: Woodstock, New York

Woodstock has been on my travel bucket-list for awhile. Most people equate Woodstock with tie-dye, hippies and the 3-day outdoor music festival, but that festival did not actually take place there. It took place in Bethel, about 1.5 hours southwest. Still, Woodstock has become a beautiful bohemian destination in its own right. My recent trip did not disappoint and Woodstock now holds a spot on my list of favorite places in the Catskills.

We stayed in a beautiful cottage that I found on Airbnb called the Grapevine Cottage. It was perfectly situated amidst a lovely stretch of Catskill forest, but also just a few minutes drive into the heart of the village. The owner of the cottage built the space with her husband on her family’s property. She moved to the US from Sweden as a child and her parents purchased the land as a bohemian retreat where horses and donkeys roamed the grounds. Today there are no farm animals about but the place is just as gorgeous as ever and it truly felt like we had slipped into a fairy tale. Here are some photos of the beautiful property where we stayed.

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There is plenty to do in Woodstock. As always I did quite a bit of research before we set out. There were a lot of things that I would have loved to do but we didn’t have the time as we only stayed two nights. We explored the shops in the village, on and around Tinker Street. There are so many beautiful shops. You could spend an entire day exploring them all, so many gems. My favorite shop was Candlestock, a gorgeous candle store that has been around since 1969.

As for meals, there are so many food gems in Woodstock! It was difficult, but I narrowed our must-try list down to 3–Cucina, Tinker Taco Lab, and Sylvia. I highly recommend all three. On our first night in town, we ate at Cucina and the food was outstanding. We shared the “Crispy Squid” appetizer. I am somewhat of a calamari connoisseur (I try it everywhere I go) and this dish was quite possibly the best one I’ve ever had. For my meal, I ordered the risotto from the special menu and it, too, was excellent. The restaurant is cozy, nestled into a big yellow farmhouse with a wraparound porch. The ambiance inside is candle-lit, warm, and inviting.

The next day we were exploring the shops on Tinker Street and stopped into Tinker Taco Lab. There is indoor seating but we arrived at the back, on the bar side, so we ate on a picnic table beside the river. It is quite a magical spot with cafe lights strung up overhead. I had a beautiful Paloma cocktail and we tried several tacos, the barbacoa, the fish, and the fried avocado. They were all excellent, but the fried avocado was my favorite–so good! We also had the refried bean side-dish and it was a perfect addition to the tacos. Most of the food had a little kick, so as long as you’re good with some spice, you’ll love it.

On our final night in town, we had dinner at Sylvia. I was very excited about this place because it looked gorgeous in photographs–I am such a sucker for gorgeous design–and it did not disappoint. It is beautiful inside & out, very sleek & elegant, and still completely inviting. The restaurant has a lovely seasonal menu and everything is served farm-to-table style. The lighting inside is a dream and the open kitchen with the wood-fired stove are so fun. We chose the local bread plate for an appetizer, the citrus whipped butter was divine; and I had the arctic char for my meal, it was cooked perfectly.

Our last meal in Woodstock was unplanned. I had wanted to have lunch at the Phoenicia Diner, but we were out of time. So we hurriedly stopped into Catskill Mountain Pizza with zero expectations and were pleasantly surprised. The place was quaint and we enjoyed our eggplant & chicken parmigiana sandwiches, the bread was so good! It was quite a “typical pizza joint” but it was filling, the staff was delightful, and it was a nice final touch to our time in Woodstock.

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There is so much to see and do in Woodstock, but with limited time I had to narrow our activities down to just a few things. Aside from dining and exploring Tinker Street, the other two highlights of our visit were Glo Spa and the KTD Monastery. The monastery is beautifully situated near the top of the Catskill Mountains above Woodstock. It was the first Karma Kagyu monastery to be built in the United States of America back in 1863. We arrived at the monastery on Saturday afternoon right in time for an afternoon tour. It was so lovely to hear about the history of the monastery and about the Buddhist philosophies. I was really excited to get some photographs of the prayer flags that surround the grounds, but it was so foggy outside that I couldn’t even get a clear shot of them. Even so, the place is stunning and it absolutely worth the visit. There is also a book store and gift shop where I purchased a set of Buddhist prayer beads that I absolutely cherish.

Glo Spa was a heavenly treat. We had a deep tissue couple’s massage. Our masseuses were named Michael and David and they were incredible angels (pun-intended). It was definitely one of the best massages I’ve ever had and the spa itself is the epitome of relaxation. You get full use of the spa, saunas, showers, and relaxation rooms with your service. So I recommend giving yourself time to lounge around in the seriously comfortable robes that they provide and to enjoy the complimentary teas and detox waters.

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We had such an amazing time in Woodstock. I loved every moment of the weekend and it was extra special because it was my 35th birthday, too. I could not have asked for a better birthday weekend celebration. I love Woodstock. There are so many other places that I want to see and explore but I do hope that I will find my way back to that beautiful little slice of heaven sometime in the future. Many thanks to all of the locals who made our visit so special and warm. And thanks to the gorgeous blossoming trees & cloudy skies that made the entire trip feel like a gorgeous Monet painting. ♥