Travel guide | Woodstock, New York

Woodstock is a great weekend NYC getaway. It’s about a two hour drive up the Hudson. I highly recommend getting there by car, but there are some good bus options, like LINE and Greyhound. For accommodation, there are plenty of cute and reasonably priced Airbnb’s for various size groups. If you’re on the hunt for a beautiful (even dog friendly) hotel, I’d recommend Woodstock Way.

OK, I’ll get the buzzkill fact out of the way upfront: did you know the 1969 Woodstock music festival actually took place about an hour and a half drive from Woodstock in Bethel, NY? I just thought you should know before you make the drive all the way up to this little town hoping to see Janis Joplin reincarnate or something…

I’m sharing the highlights of a long weekend here, which you can squeeze into a one night, two day visit:


Day 1


Start your day off with a wood-fired bagel at Mud Club. Yeah that’s right, ya heard me. Like a “watch your bagel go right into the flames” type of wood-fire. Mud Club is a cozy little breakfast joint serving coffee, bagels and sandwiches. It has an eco-friendly mission and is more than happy if you come in with your reusable coffee mug.



Get some of that good country air in just a 7-8 minute drive from the town square of Woodstock. Head up Meads Mountain Road to the trailhead of Overlook Mountain. We didn’t hike to the top, as there was so much snow, but I hear the views are incredible! I can’t wait to visit in summer (or with the right winter hiking gear).

Don’t miss a quick tour of the Buddhist temple across from Overlook Mountain’s trailhead on your way back. Behind the temple, there’s even a tiny wooden church dating back to the late 1800’s! It’s open all day for anyone to use as a place to pray. It was quite breathtaking standing before this church in silence with the snow coming down, imagining how many people have come here over the past century.

I won’t pretend I have a full grasp of the religious movements and events that have been injected into Woodstock over the decades to make it what it is today, but it is apparent that for many, Woodstock is a place of deep spirituality.



Head back down to Mill Hill Road to Garden Cafe - it’s the sweetest little plant-based restaurant. Don’t worry, it’s not just salads and smoothies. We had lasagna and a burger that really filled us up after a cold day. The staff are so warm and you can tell their customers have become more like a community.

To cap off the evening, you’ll meander behind a few buildings off of Tinker Street to find Tinker Taco Lab. I hear it’s a delicious and relaxed taco place by day, but the bar in its attached cabin is what we came for. With picnic tables and string lights outside, I imagine it’s hopping in the summer. We took our drinks outside with Mowgli so as not to disturb the crowded little cabin bar…and it worked out just fine! Another option is R&R Taproom, which is a lively little bar hosting live music and events.

Day 2


Shindig is probably one of the more well known restaurants in Woodstock, and I’d recommend trying it for breakfast. It’s a funky sit-down spot, so you can enjoy a slow morning there. After breakfast, walk along Mill Hill Road and Tinker Street (the main drag of downtown Woodstock) to peruse all of their cute (albeit very hippy), shops and galleries.



On your last stop before heading out of town, I recommend Woodstock Brewing for some drinks, food and board games. Take note that it’s not actually in the downtown of Woodstock, but in the nearby town of Phoenicia. The drive there is beautiful - with a full view of the mountains while you meander through some small towns. So it’s a great last drive before heading back to that #concretejunglelife.

Our trip to Woodstock was quick. But sometimes all you need is a little reset from the craziness of the city to feel like you can breathe again. I think there’s so much more to do. So I’m looking forward to returning to Woodstock in another season.

Where are some of your favorite upstate escapes out of the city? I’m always on the hunt for a new little town to visit.

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