Woodstock, NY: great escape from the city

We did a couple's trip to Woodstock, NY as we just wanted something cozy and fun outside of the city, but still within the two hour threshold. I had read on some blogs and travel features about the new Woodstock Way hotel in the heart of Woodstock. This was our first trip to this hipsterfied, rock and roll destination and we will definitely make this a mainstay on our escapes from New York.

Lodging

Woodstock Way was fantastic. We had a little different stay than most at the very modern, refurbished property. That's because our friends were bringing their dog, so we both opted in staying at the properties two remaining original cabins, the Lone Wolf Cabin and the Waterfall Cabin. The Lone Wolf cabin was more updated than the Waterfall, but the Waterfall had all the charm and one heck of a view. If it hadn't been so cold during our visit, I would've had more than just a coffee and everything bagel from Mud Club. The reception is gorgeous, staff is helpful, and they make a wonderful flat white. They've kept the original rock and roll vibes of Woodstock, but modernizing it. There's no restaurant/bar on premises, so we had brought bottles of wine and enjoyed them by the large fire pits with view of the waterfalls. Pure magic.

Next time: I'd try staying in one of the new, more modern rooms at Woodstock Way. Loved the Waterfall Cabin, but love their decor and finishings on the new ones and wouldn't mind a little more comfort.

Expert tip: This place has received some amazing press, no surprise from seasoned hospitality veteran owners Ryan Giuliani and Jesse Halliburton. Unfortunately that means that it's now more expensive and harder to come by reservations. Still worth it, but book in advance for weekend stays!

What to do/Eat/Drink

We treated this weekend as an indulgent, fun weekend, so although hiking is definitely something we wanted to do, going in mid-December did not permit that. We recommend the following:

Explore the town of Woodstock. Tinker Street is filled with cute shops, many with the nostalgic trinkets of the 1960's. I will say I was a little disappointed with the record shops in town as they were so expensive, but supply-demand, I get it.
We arrived to Woodstock Way after dinner time and pretty late for this town, so we pretty much only had time for hitting up a dive bar in the hopes of food. Two blocks from the hotel was the Station Bar & Curio. Definitely a locals scene, hipsters a plenty, but great music and fun. We braved getting one of the $2 hot dogs... fine if you're starving, but there's plenty other choices in town if you have another choice. And plus, there's a pool table!
Snag bagels at Mud Club, which is EXCELLENT. The catch is, they run out. I had to wait 20 minutes for the next everything bagels to come out of the woodburning stove, but they were worth every minute. Also, great spot for coffee with the biggest milk selection I've ever heard of. I almost felt odd ordering actual milk, and not some plant based version.
We spent an afternoon at Woodstock Brewing, which is out-of-town and really closer to Phoenicia. The uber wasn't cheap and took a while to snag one, but was great to taste some local beer and ciders while playing Jenga and Connect Four. A perfect winter Saturday with Friends.
Woodstock Brewing has decent food, but for an authentically cool, laidback, and nostalgic trip to the Catskills (and isn't bar food) that is just down the road from the brewery, visit the Phoenicia Diner. The diner has all different types of food and is tasty, just beware that the portions are enormous. We didn't have to wait because we went in the middle of the afternoon, but I hear the lines are long if you hit it during prime brunch time.
Tinker Taco: definitely want to come back in warmer months to sit outside, but cute cafe lighting and bar with decent craft cocktails. I had a Mezcal-rita. Fun, laidback environment. Didn't have tacos this time, but will be back to give my tough California taco review next time.
Silvia was a highlight for dinner. It was well-crafted farm to table cuisine in a beautiful environment. I made reservations a couple weeks in advance as it does get busy on a Saturday night. Would recommend for anyone staying in the Catskills or Hudson Valley looking for a great date night and/or group dinner environment.
We had breakfast at Shindig before we left back for NYC. Local, great mainstay. Nothing fancy but nice local ingredients for decent food

Next time:

Music/culture there's a reason this city is famous for it. I'd definitely check out a gig at either Bearsville, Levon Helm Studios, or the Colony. There's also a bunch of creative studios that offer classes on jewelry, tie dying, and other crafts and yoga studios dot Tinker Street.
Hiking, especially the Overlook Mountain Trail
Although I loved staying at Woodstock Way, I wouldn't mind staying in an airbnb or a VRBO up here. We thought the eating establishments were lovely, but for a long weekend, think cooking with all the local ingredients and being able to play LPs on a turntable would be fun.