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Hiking in Woodstock, New York

Activities for a weekend in Woodstock NY

Only a 2 hour drive from New York City, Woodstock is a mountain town that really packs a punch.

Famous for being the namesake of the famous music festival of the 60s, this little township is the perfect place to escape the city for a relaxing weekend. It draws plenty of tourists with its hippie culture and thriving arts scene, especially in the Fall when the surrounding forests develop a colour spectrum that ranges from bright greens and yellows, to oranges and reds.

I recently spent a weekend in Woodstock, exploring the area with my parents when they came to visit Rob and I in New York. Here’s some activities for a weekend in Woodstock NY!


Airbnb house in Woodstock, New York

Where we stayed:

We booked an Airbnb vacation home just outside of the township. It was wonderful to stay so deep in the quiet woods, especially after the craziness that is NYC! Our host said that there are a local family of bears that can sometimes be seen out there, though unfortunately we didn’t spot them (I really wanted to!).


Things to do in Woodstock:

Vintage shops in Woodstock, New York

Wander through the township

Taking a walk through the town centre of Woodstock is an essential part of any visit. Start at the Village Green, then walk in either direction along Mill Hill Road. Here you’ll find countless antique stores, arts and crafts shops, boutique clothing, flea markets, and giftwares.

The town has a surprising number of great food options. My favorite hangout was Garden Cafe with its hearty vegan meals, but some others you can check out are Bread Alone Bakery, Catskill Mountain Joshua’s Cafe, and Peace, Love & Cupcakes.

Snow boots - Woodstock, New York

Do a hike

You absolutely can’t visit the Catskills without doing a hike, and luckily there are options around Woodstock for all fitness levels.

An easy one to start with is the Kaaterskill Falls, which is a 1.3 mile trail popular with both tourists and locals. For something a little longer, you can walk around the picturesque Cooper Lake on the flat and easy road that circles it. For a more challenging hike, try Overlook Mountain which is a 4.6 mile trail providing a spectacular view of the Catskills. Make sure you arrive early, as parking is limited.

Opus 40 in Woodstock, New York

Check out Opus 40

Opus 40 is just a 10 minute drive from Woodstock. Built in an old quarry, this bluestone sculpture garden took 37 years to create and is spread over 6.5 acres. It has ledges to climb on, tunnels to explore, and a gorgeous garden to admire. Entry is $10 per adult, $7 students and seniors, $3 children (ages 6-12), and children under 6 free.

Karma Triyana Dharmachakra Tibetan Monastery in Woodstock, New York

Visit a Tibetan Monastery

Karma Triyana Dharmachakra is a Tibetan Monastery hidden in the mountains of New York. It seems an unusual building to find in this area, but somehow it fits nicely into the leafy surroundings. The exterior of the monastery has brightly colored orange and red linings, and the interior of the prayer room has a soft golden glow and intricate decorations.

The opening hours of the monastery are sporadic as you can only enter the prayer room between teachings, so be sure to check the website for visiting times before you arrive.

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