Weekender 0

Woodstock, NY

For many, the word Woodstock conjures up images of tie dye, hippies, and free love at the 3-day outdoor music festival… that did not actually take place here. (It actually took place in Bethel, which is about an hour and a half southwest, close to Narrowsburg.) That didn’t stop Woodstock from becoming a bohemian destination though; for many years, the streets were lined in touristy gift stores and head shops. Presumably, like many others before us, we had stopped through on occasion–but didn’t ever spend much time here. There just wasn’t much to do. But during the past couple years, Woodstock has taken a major turn for the better. With great new shops, restaurants, and lodging available, it’s a definite contender for the coolest destination in the Catskills. (Plus, it’s home to one of the best hikes in the region!)

To get here by public transit, you can take the Trailways Bus directly into town; it drops off in the center of Woodstock. That said, we’re big fans of renting cars to enable so you’re able to explore the area a little more or go on the nearby hike.

Where to Stay in Woodstock: Cabin on a Stream, or Groovy Boutique Hotel

We recently spent three days and nights at Woodstock Way, a rustic-chic cabin retreat in the heart of Woodstock. Our cabin, The Lone Wolf, was the perfect place to cozy up and disappear for the weekend. The cabin featured a woodburning stove, a king-size bed, a patio, and a kitchenette with a little sunroom for dining, which overlooks the creek. Speaking of the creek: just a bit further downstream, there’s a waterfall with a small swimming hole on the Woodstock Way property. The last and possibly biggest selling point for Woodstock Way is the absolute lack of needing a car–it’s within walking distance from Trailways Bus, which leaves many times from Port Authority daily. And though it’s super close to the heart of town where the bus drops off, you’re not sacrificing privacy as the cabins are tucked far behind Main Street in the woods. If you don’t need a whole cabin, which sleep four, rent one of their private rooms and save a little dough.

We also stayed at, and are big fans of, the Hotel Dylan. We’d passed it’s “Peace Love Stay” signs many times–it’s right on Route 28, the highway of the Catskills–but for some reason, never googled it. After it’s appearance in the New York Times, though, we were inspired by the photos and booked a trip right away. The roadside motel-style lodging is much more modern and chic than you might expect from it’s exterior. The rooms have the best wallpaper ever (seriously) and are decorated with music-themed decor like Crosley turntables (complete with a small selection of records) and oversized concert posters and photos. Our room also had a mini-fridge, a huge cozy chair, two beds, and a pretty sizable T.V.; bathrooms were stocked with C.O. Bigelow products. Our favorite part of Dylan, though, was their nightly bonfires that served as a gathering space for guests and travelers. We met some really cool people around the campfire, telling stories, sharing backgrounds and comparing itineraries. The only possible drawback is that it’s about a ten minute drive to Woodstock proper–but that also puts you ten minutes closer to the nearby towns of Mt. Temper and Phoenicia. We also can’t wait for next summer, when the construction of their spa and pool will be complete.

What to do in Woodstock: Explore Main Street, Drive Scenic Route 28, Hike To An Old Mountaintop Hotel

 Once spattered with hippie head shops, Tinker Street has gotten a fresh batch of new boutiques that puts it on #1 on our list for shopping in the Catskills. First up, Pacama Handmade is a showroom and retail space for the work of Cedric Martin and other like-minded artisans working in wood, ceramics and textiles. When we popped in, Cedric’s wife Rebecca was simultaneously manning the store and spinning wool into felt. A bit further down Tinker Street is Shop Little House which is well-stocked with gifts and things for the home, both vintage and new. Woodstock General Supply and Eco-System are both beautiful stores where outdoor lifestyle meets fashion, both with a great selection of apparel, accessories and gifts. We could go on and on with the shopping–some other staples include Anatolia Rugs, Fruition Chocolate, and Ardnaglass. For bookworms, don’t miss The Golden Notebook. Also worth noting: there’s a flea market on weekends in the heart of town behind the public parking lot. (Psst, buy something from the produce guy–he’s got great stuff!)

If you have a car for the weekend, there’s even more shopping! Just down the road, Scandinavian Grace is a must-stop, where antiques seemlessly meet design thanks to owner Fredick’s curation. We also love Migliorelli Farm stand on Route 28. Most of all, we also love driving aimlessly up and down major roads and backroads, looking for yard sales and barn sales. Even if you don’t find any, driving is a lovely way to take in the Catskills.

For people seeking outdoor adventure, our favorite way to spend time in Woodstock isn’t in town–it’s right outside it at a hike called Overlook Mountain. About a ten minute drive from the heart of Woodstock takes you it’s trailhead. The hike is about three hours round trip, which includes some time at the top for sight-seeing. It features multiple overlooks at the top as well as hotel ruins from the early 1930’s; a gravel path makes the hike considerably easier to do year-round than others in the area.

Last, it would be a shame to visit Woodstock and not experience the art and music culture here. One of our favorite destinations is the lovely outdoor landscape and sculpture park and museum called  Opus 40. Imagined and built by sculpture artist Harvey Fite, the project took him almost 40 years to construct in it’s current form; sadly, he passed away in a fall during it’s construction. For indoor art appreciation, stop into Center for Photography and check out their (free!) galleries. Besides being a non-profit exhibition space, it also serves as a facility housing a darkroom, a digital library, and offers an artist in residency program. Stop in, maybe donate a couple bucks, and spread love. Aside from these very specific recommendations, Woodstock is literally brimming with great galleries and shops. It’d be impossible to name them all, so carve out a chunk of a day and discover them yourself.

Where to Eat and Drink in Woodstock


Woodstock has a good variety of places to eat, with some new options along with the staples that have been around for some time. For breakfast, Shindig is the newest option in town serving fresh, local, seasonal fare. It’s hands down our favorite place to eat in Woodstock–be it breakfast, lunch or dinner. Say hi to Allison, the manager for us! For lunch, Woodstock Provisions is new in town as well, serving up mouth-watering paninis and sandwiches. Menus change often and are posted on their Facebook page. Garden Cafe is also wonderful, offering up lots of vegetarian and vegan options. During warm weather, their outdoor seating in the garden can’t be topped.

For dinner, the Italian cuisine at Cucina absolutely cannot be topped. The restaurant is housed in a restored farmhouse with a cozy bar to hang out in (if you didn’t bother making reservations–which you should!) The main courses are a little on the pricier side, but they’re 100% worth the splurge. For something more casual, check out the beautiful Tinker Taco Lab, with it’s simple menu of five types of tacos and two types of tamales. We’re into that–there’s beauty in simplicity. It’s tucked behind some other buildings on Tinker Street, so it’s a little tricky to find, but worth the effort.  Last, we enjoyed cocktails and the food at the Commune Saloon. It’s right next to music venue Bearsville Theater, so check out their schedule when you’re planning a trip here!

If you’re visiting the region with a car and willing to drive for your meals, we always send people to Peekamoose and the Phoenicia Diner. Peekamoose is described as “the Gramercy of the Catskills” and for good reason; every meal here is more mind-blowing than the next. Don’t fill up on the bread and leave room for dessert. Similarly, the Phoenicia Diner is serving the breakfast and lunch of your dreams; if it’s too long a wait, and you just want to check it out, try your luck at the bar, which is open on weekend nights.

You Might Also Like