How To Spend A Weekend in Woodstock

How To Spend A Weekend in Woodstock

While I credit my parents with a lot of my distinctive qualities, I don't credit them for my love of the outdoors. For that, I give credit to my younger brother Eric. He's the extreme one of the two of us. The one who hiked half-dome, who went camping at Olympic National Park on his own. The one who knows his way around without google maps, who skis double-black diamond after a few lessons. Eric adores hiking, while my feelings about it are lovely but lukewarm. I enjoy it in small bursts. I see nothing wrong with glamping, and kind of hate pitching a tent. My fiancé Brandon though- he's on Eric's team. He has an REI credit card. He lived in Colorado for a year. He owns all the camping gear we could ever need. For Brandon's birthday this year, I decided to spend money on an experience rather than a thing. I booked us a weekend in Woodstock on a huge farm, through Tentrr. It was a happy medium for both of us. Brandon got to sleep in a tent, and cook over a fire; I got a real mattress and a town with adorable shops.

The weekend was simply marvelous, and I left in awe of the high quality food, shops, and sights in Woodstock. I highly recommend you grab onto one of these last summer weekends and make your way out there. If not because I told you so, then at least for the burger at Shindig's. More on that below. 

Friday: Arrive in Woodstock and enjoy the evening. If you're camping like we are, come packed with ingredients that would make for a delicious dinner over the fire. We came with a pre-packed salad, a chilled bottle of wine, and made a hot + delicious chicken dish. We layered the bottom of a cast iron pan with onion, fennel, and tomato. Then we drizzled it with olive oil and salt, and placed boneless, skinless chicken thighs atop the veggies. We covered the whole pan with foil and put it over the fire. After 20 minutes, I pushed the veggies to the sides of the pan, and used tongs to turn the chicken and place it onto the pan to get crispy! Drink wine, eat dinner, look at the stars, and enjoy your first night out in the wilderness. 

Saturday: If you're going for a hike in the summer, I recommend you wake up early as it gets very hot by 10AM. There are some great views, such as Overlook Mountain (tiring, but incredible) and Kaaterskill Falls. Cook up a protein-heavy breakfast or stop by Bread Alone Bakery on your way out; they open at 7am.  Another tip: bring snacks and energy bars with you on Friday so that you don't have to make an extra stop at a convenience store. 

Once you're done with the hike, either head home to clean up, or go straight into town like we did! Here are some of my favorite gems from the strip of stores on Tinker Street:

Woodstock Library: Check if they are having a book sale. I believe they happen every two weeks and are really superb. Brandon and I each found 10+ books and bought them for $1.50 each. There were some great new books, as well as classics and just a great assortment overall. I highly recommend! 

Shindig: OMG the food at this place! We got the burger which was out of this world good. I mean squishy bread, juicy burger, perfectly melty cheese, the works. I had a lobster roll which was on the specials and divine too! P.S the side orders are very large! We had a lot of extras to take home and nosh on in our tent. 

Garden Cafe: delightful vegan food right in the heart of the town! We didn't eat here but heard great things 

Timbuktu: You'll be able to pop into so many shops on Tinker street, but this one was my favorite. It had an incredible mix of handmade, artisan items as well as cheeky, playful things like spoons that say "cereal killer" :) I bought a piece of woven wall art for our apartment

After your dining & shopping, head over to the flea market which is about a 5-minute walk away. There you'll find a guy giving massages, another dude selling vintage cast-iron pans, and just about any crystal your heart could desire. In the back, there's a lady selling luscious goat milk lotion, and a farmer whose blueberries were perfect for snacking on as we walked. 

At this point, you'll need to decide what you're going to do for dinner. While you can definitely go home, rest up, and head out on the town, here is what I recommend: Order enough at lunch so that there are leftovers, and then buy supplements in town (a few shops including Sunflower Cafe & Market) for a light dinner al fresco. Especially if you're going on a hike, you'll probably eat a later lunch, and be okay with a smaller dinner. We went home around 7, read in our tent, then cracked open a new bottle of wine and ate, drank, and talked loudly to scare away the bears. City kids, ya know? It truly was perfect. 

Sunday: My whole life, my parents would stay somewhere until 10PM on Sunday and only then head home. This method ensured we got to squeeze every last drop out of a weekend way AND avoid all traffic. Brandon and I have recently learned that is not our style. We prefer to pack up in the morning, do something fun, and be out on the road shortly thereafter. We like to stop on the way for groceries, and get home in time for dinner + a show; probably Game of thrones! 

So, with that being said, we woke up Sunday and did yoga outside. It was so refreshing and calming. We drank coffee, sat and read for a bit, then began to pack. By noon we were on the road, heading to one of the best diners ever. 

If you're in Woodstock, you must make the drive up on Sunday morning to Phoenicia diner, which is a 20-minutes drive away! Be prepared for a wait, but it goes faster than you think. Pro-tip: order the "catskills muddy water" from the truck outside while you wait to get your caffeine boost. You can also order food + cocktails straight from there if you prefer, but it's a limited menu, We ordered a skillet with eggs, greens, and cheese (yes please), and "shrooms on a shingle"; both were delicious. Near Phoenicia diner is the Emerson Resort & Spa, where you can go for a lovely massage or treatment if you've got extra time on your hands. 


I hope you enjoyed reading about our weekend in Woodstock, and that these tips will help you plan your own little getaway! Please feel free to post questions or comments below :)

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the weekend cast

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