The Relax in Woodstock Blog

This is a collection of our favorite things to do and places to eat in and around Woodstock, New York. We bought our first house ever in Woodstock in 2017 and spent a good majority of our free time in the area between 2017 and 2019. Since we started renting the house to guests in 2019, we continue to stay at the house regularly when we want to relax with our family and friends or enjoy some of our favorite annual activities in Woodstock.

The collection below is presented in chronological order with our most recent posts at the top. If you’re looking specifically for food recommendations, check out our Places to Eat page or or use the search box below.

The Best Live Music Venues Near Woodstock, NY
Things To Do Rick Bashkoff Things To Do Rick Bashkoff

The Best Live Music Venues Near Woodstock, NY

Long before and ever since 1969, this town has served as a sanctuary for iconic musicians, world-class songwriters, and vibrant local talent. Today, it remains one of the best places in the Hudson Valley to experience performance art up close. Whether you're looking for an intimate barn session or an outdoor summer concert, here are five of the best live music venues in and around Woodstock, New York.

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The Best Activities for a Summer Trip to Woodstock, NY
Things To Do Rick Bashkoff Things To Do Rick Bashkoff

The Best Activities for a Summer Trip to Woodstock, NY

Summer is prime time in Woodstock, New York. Long sunny days, lush green mountain foliage, and a bustling town square make the Catskills the ultimate summer destination. Whether you’re cooling off in a swimming hole, spending an evening listening to live outdoor music, or exploring local farm stands, summer in Woodstock offers an unforgettable mountain escape.

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The Woodstock Pub in Woodstock, NY - Review
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The Woodstock Pub in Woodstock, NY - Review

A good old fashioned pub in the heart of Woodstock. This restaurant and bar has a great local, small town vibe while serving high quality food and drink options. One of the best parts of this restaurant is eating in the patio dining room that is situated right on the edge of the sidewalk.

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We promote the local businesses that make Woodstock so attractive to weekend and seasonal visitors because we buy, shop and experience them ourselves since we became a part of the Woodstock community in 2017. We currently to do not have any commercial relationships with any entity we mention here.