After 15 years in Brooklyn and weekends escaping to the Catskills, I eventually took the plunge and bought a home in Woodstock, New York. What started as a weekend escape became home, and it’s been one of the best decisions I’ve ever made.

As a lifelong New Yorker, I grew up in Western New York and spent much of my adult life between New York City and Upstate New York. I’ve experienced firsthand the transition from city life to country living, an...