Woodstock
This page may contain affiliate links, which means we may receive a commission if you click a link and purchase something that we have recommended. Please check our disclosure policy for more details.
Woodstock, a sleepy little town nestled within the Catskill Mountains in New York’s beautiful Hudson River Valley. Known as a mecca for artists, musicians, and writers before the famous 1969 music festival, the creative spirit continues to flow and can be felt throughout. It’s the perfect place for a short, peaceful escape surrounded by good vibes, great music, and natural spaces.
Places of Interest
Ashokan Reservoir: The Ashokan Reservoir is located at the eastern end of the Catskill Park, just outside of Woodstock. Cycle or walk along the 2.8 mile-long Ashokan Promenade along the reservoir’s southern shore to soak in the breathtaking views of the Catskill Mountains.
Comeau Property: A lovely space for a leisurely walk through the trees in solitude, with friends, or even a furry friend. Comeau Property managed by the Wooodstock Land Conservancy, which actively maintains the current uses of the property, protects its natural features, and limits its future development.
Overlook Mountain: Hiking the Overlook Mountain Trail for sunrise or sunset is a must when in Woodstock. The steep trail is easy to navigate–a bit boring–yet offers magnificent views once you reach the top. Explore the hotel ruins, climb the fire tower, and soak up the views. Budget one to one and a half hours for the ascent. Heads up, this hike has the highest population of Timber Rattlesnakes in the Catskills.
Karma Triyana Dharmachakra: This Tibetan-Buddhist monastery sits atop Overlook Mountain. This site is the North American seat of the 17th Gyalwang Karmapa, Ogyen Trinley Dorje, who is head of the 900-year-old Karma Kagyu lineage of Tibetan Buddhism. It’s generally open quite early in the morning until dusk.
Opus 40: Created by pioneering artist and professor Harvey Fite, Opus 40 is a world-famous nonprofit sculpture park and museum. There’s more than 60 acres of meadows, forested paths, and bluestone quarries. Technically in Saugerties, not Woodstock, but a stone’s throw away.
Tinker Street: Tinker Street is a great shopping area and one of the town’s main streets. Stroll up and down while popping in and out of the various art studios, cafes, and galleries. This is the place to find postcards, shirts, hats, and other souvenirs, plus unique finds from local shop owners.
Candlestock: The coolest candle shop with an awesome Candle Mountain inside (the mountain started in 1969 with a single drip candle and is now over 6 feet tall!). The shop sells a variety of unique candles, mostly locally sourced and handmade. I love coming here for gifts as well as for basic daily-use candles.
The Golden Notebook: Loved this little book nook. It had some great titles and authors, as well as advocates for social justice + change through writing/ reading. Fun to browse and even better to buy, as supporting a local small business is always where it’s at.
Rock City Vintage: My favorite vintage shop off of Tinker Street! The owner is a true delight and even makes some of her own unique clothing designs, which are sold in this shop. A true gem to hit up for beautiful, ’70s-inspired pieces.
The Colony: This restored 1929 theater is the place to go for music, arts, and comedy events. Be sure to check-out their website for all upcoming events. Book ahead of time if you’re planning on visiting in the summer, as it fills up quickly!
Travel Tip#1: Woodstock, the famous three-day music festival, was actually centered in Bethel, the town next door. Be sure to visit Bethel to check out the Bethel Woods Center for the Arts, as well as immerse yourself in the awesome music scene in both Woodstock and Bethel while visiting to get a true taste of the area’s culture.
Food
Bluestone Roasting Company: This little place is actually in neighboring Saugerties, but it is a great place to stop for coffee on a sunny day. I loved sitting on the outdoor patio/balcony area whilst enjoying my morning coffee.
ImmuneSchein Tea Haus: Full of wonderful teas, unique ceramics, and other worldly specialities, this shop is owned by the sweetest and most talented couple. They make you feel at home: helping pick out your tea, answering any questions, and just having a lovely conversation. Tea Haus carries tons of organic loose leaf tea and their popular handcrafted ginger elixirs.
The Mud Club: My absolute favorite place to grab a bagel and coffee, no matter what time of year! The cabin- and woodsy-themed eatery serves up phenomenal wood-fired bagels, which can be ordered with cream cheese, different toppings, and alongside cafe beverages. Their hours have been in-flux since the pandemic, so check online beforehand.
Harana Market: This place is to die for! A little Filipino and Asian Oasis off the beaten path, Harana Market combines the best aspects of an Asian market and Filipino Deli. Their lutong bahay (homestyle) Filipino food menu rotates, but is always consistent in quality and flavor. Due to their small size, ordering ahead is recommended as they do sell-out due to popularity.
Bread Alone: Bread Alone is a family-owned, values-driven bakery. They bake with organic grains and serve “honest food, create prosperity for our people, and minimize further harm to the planet.” In addition to having several bakeries scattered around the Hudson Valley area, you can find their goods stocked at smaller stores throughout the region.
Mountain Gate Indian Restaurant: An unassuming Indian restaurant off the main road, I was recommended this place by my Airbnb Hostess. It did not disappoint! They can take a bit longer to prepare the food than other places and their take-out wait can also be longer during evenings and weekends.
Garden Cafe: A community-focused in the heart of Woodstock. Garden Cafe is well-known for its fresh, organic, vegan food. Eat inside or during the warmer months, enjoy their outdoor garden seating.
Rip Van Winkle Brewing Company: Not in Woodstock, but nearby. This brewery-restaurant has lots of tasty beer on tap, including their own in-house selections. It can get fairly busy here, so either arrive early or make a reservation. I recommend eating in town and then heading here afterward.
Travel tip #2: Many placesin Woodstock are closed during the middle of the week, so plan accordingly and check restaurant hours ahead of time.
Transportation and Accommodation
Woodstock is best enjoyed via car and by using your own two feet. Getting into the area is a bit tricky without a vehicle, as public transportation is not common in the Hudson River Valley. Once in town, find a parking spot and explore the area on foot. Parking on weekends is fairly challenging, as that’s when the town is busiest. If you arrive around 10 or 11 am, you’ll beat most of the weekend rush.
Accommodation varies throughout the year, with summer and concert/event times being the most expensive. There are lots of little bed and breakfasts to choose from, but I recommend Airbnb. The Hudson River Valley has gorgeous homes to rent for a couple of days, as well as simple rooms. If you’re on a tighter budget and have access to a car, staying in neighboring Saugerties or a little further from town will help with that.
Travel tip #3: Staying outside of Woodstock in neighboring towns such as Saugerties or Kingston can make your stay more affordable, especially during peak season and when concerts and events are happening.
Climate
Similar to the rest of Upstate New York, Woodstock experiences all four seasons in varying degrees. Summer is one of the best times to visit Woodstock to truly soak in the area’s laidback vibe, enjoy the amazing season farm-to-table cuisine of the Hudson River Valley, and be able to explore the breathtaking natural spaces. Spring can be a bit muddy and winter on the colder side. In addition, the snow and ice during winter months can make it challenging to drive in the area due to the windy roads and hills. September and October offer cooler temperatures compared to the summer months, which is more ideal for comfortable days walking around.