Woodstock, NY Vacation Rentals

Woodstock, New York Travel Guide

Before you get excited, the world-famous 1969 Woodstock music festival actually took place in Bethel, a town 60 miles away from Woodstock. That being said, the town itself is a leafy haven for culture junkies with an incredibly rich arts scene. It’s a romantic town settled in the Catskill Mountain range and has been the source of inspiration for tons of musicians over the decades. Woodstock has an iconic small-town feel as it’s resisted development from hotel chains and even cell towers -- so don’t expect your phone signal to be impeccable. But if you’re looking for a little bucolic getaway, Woodstock is one of New York’s finest gems.

Things to Do in Woodstock, New York

One of the best things to do in Woodstock is go shopping along Tinker Street and Mill Hill road. The colorful street is filled with quirky mom-and-pop shops that make up the town’s vibe. Browse vintage bookstores, boutique chocolate stores, and arts and craft shops. Listening to live music is another great thing to do here, as the town still carries much of the novelty and pride of the festival that happened almost 50 years ago. When you don’t have anything to do, go people watching in the town center, Village Green, or hike up to Overlook Mountain for some great views. And, for a peaceful retreat from everything, visit the Karma Triyana Dharmachakra, a monastery that looks like it’s been plucked from the Himalayan countryside.

Best Time to Visit Woodstock, New York

Summertime in Woodstock is definitely the best time to visit. The weather is nice, the shops are open, and the town's energy really comes alive. Don't be afraid to visit during the shoulder months of spring or fall for a chillier break.