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 Ski Areas Near Woodstock, NY
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The Best Ski Areas Near Woodstock, NY

Located in the the Catskill Mountains and a short drive from the Berkshires, Woodstock is a great place to camp out for a Northeast winter ski trip. If you’re headed to the Catskills for some skiing, here are five of the best ski areas near Woodstock, New York.

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The Best Activities For a Winter Trip to Woodstock, NY
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The Best Activities For a Winter Trip to Woodstock, NY

Winter in Woodstock is a magical time of year. With the busy seasons of the summer and fall in the rearview, the area, retires for the winter into an even quieter and more cozy escape. It provides the perfect setting for a weekend of skiing, snowshoeing, hiking, or just bundling up in a cozy country home to catch up on sleep, work and life. In this blog post, we'll explore the best things to do in winter in Woodstock, New York.

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The Best Activities For a Fall Trip to Woodstock, NY
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The Best Activities For a Fall Trip to Woodstock, NY

As the leaves change and the air turns crisp, Woodstock, New York, comes alive with a myriad of fall activities. Located in the Catskill Mountains, this picturesque town is a popular destination for leaf peepers, outdoor enthusiasts, and art lovers alike. Here are some of the best things to do in Woodstock in the fall.

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Silvia in Woodstock, NY - Review
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Silvia in Woodstock, NY - Review

One of our absolute favorite places to eat in Woodstock. This high-end restaurant serves the highest quality dishes and has an upscale feel. They have both indoor and outdoor seating with the outdoor being one of the nicest, most relaxing outdoor venues for dinner in the area.

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Cucina in Woodstock, NY - Review
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Cucina in Woodstock, NY - Review

Specializing in seasonal and local ingredients, this is a a unique food experience in the Catskills. Cucina has a perfect relaxing dining room. The outside is nice and all but the inside is perfect. Very relaxing and simple. We feel very comfortable at Cucina.

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Garden Café in Woodstock, NY - Review
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Garden Café in Woodstock, NY - Review

A genuine favorite in the heart of Woodstock. The ingredients are of the highest quality, all dishes we order are excellent and the staff is very friendly. A vegetarian and vegan friendly menu that includes soups, starters, salads, entrees, desserts and a kid menu.

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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.