Woodstock, located in the picturesque region of the Catskills in New York, offers a variety of enjoyable activities and attractions. One of the most popular activities is exploring the Woodstock Artists Association & Museum, where visitors can appreciate works from contemporary and historical artists. The town is also known for its connection to the famous 1969 music festival, even though the festival itself was held in Bethel. Nonetheless, the town embraces its musical legacy, and visiting the Woodstock Music Shop or attending a live performance at local venues can offer a taste of its vibrant music culture.

For nature enthusiasts, Hiking in the Catskill Mountains provides breathtaking views and a chance to connect with the area's beautiful natural landscape. Trails such as Overlook Mountain offer both adventure and scenic beauty. A visit to Opus 40, a large environmental sculpture park created by artist Harvey Fite, can be both a meditative and inspiring experience.

Shopping and dining in the town center is also a favored pastime, with an array of eclectic shops, galleries, and restaurants. The local cuisine ranges from casual cafes to fine dining, often featuring locally sourced ingredients. Lastly, exploring spiritual and wellness retreats can be a unique way to experience Woodstock's tranquil atmosphere, with various centers offering workshops, yoga, and meditation sessions. These activities collectively make Woodstock a destination rich in art, culture, and natural beauty.