Woodstock, New York, is mostly famous for being the namesake of the famous music festival of the 60s. Only a 2 hour drive from New York City, this little town still draws in crowds with it’s hippie culture and thriving arts scene.

This little mountain town is a perfect place to spend a relaxing weekend, especially in Fall when the leaf colors range all the way through bright greens, yellows, oranges, and reds. Here’s how to spend a weekend in Woodstock NY.


Woodstock, New York

Taking a walk through the township 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.

Where to stay: Morning Glory B&B Woodstock

Hiking in Woodstock, New York

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.

Woodstock, New York

Opus 40 is 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.

Where to stay: Enchanted Manor of Woodstock

Tibetan Monastery, Woodstock, New York

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.

Where to stay: Hotel Dylan

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