Happy Trails

By   |  David Morris Cunningham  |     |  Community Spotlight

For over 270 years, people have been coming to Pawling to seek a quieter life, join a tight-knit community, and forget about the outside world. While other Hudson Valley towns have had uptimes and downtimes throughout the years, Pawling has maintained an even keel out of the spotlight, with its early history setting the template for the village as it stands today. Founded in 1742 by Quakers, who built the historic Oblong Meeting House, Pawling was the first U.S. community to reject slavery, and refused to take sides during the Revolutionary War.

Tucked within two square miles is everything needed to feel at home. There’s an abundance of small, family-owned shops; an ample and inviting bookstore; a thriving farmer’s market with its own petting zoo; restaurants serving unpretentious food at reasonable prices; cafes where everyone seems to know each other; and lots of great swimming holes and hiking trails. But even those just passing through will feel welcomed. When hikers traveling north on the Appalachian Trail from Georgia reach the trail shelter near Pawling, they’ll find lodging, showers, and something they haven’t seen for the previous 1,445 miles: a small lending library, maintained by the Pawling Free Library, where hikers are encourage to take or leave a book. If there’s one thing the people of Pawling appreciate, it’s anyone who decides to strike out and leave the hustle and bustle behind.



There’s a generational shift happening in Pawling, with the median age creeping downwards, and houses that have been in the same family for over 50 years are finally hitting the market as their owners age. Young couples that being house-hunting in Westchester are increasingly discovering that their dollar goes much further in southern Dutchess County. Pawling’s busy civic calendar makes it ideal for families. Every weekend it seems as if there’s a concert or a fair going on.

In fact, weekends are when Pawling truly comes alive, and with good reason: Thanks to the Metro-North station at its center, Pawling is a popular location for weekenders from New York looking for the solace of small-town life. Plus, businesses are beginning to flock to Pawling. Currently, popular spots include Is a Burger hamburger restaurant; Daryl’s House Club, a restaurant offering live music; and the Blue Olive, an artisanal oil and vinegar shop. And while most weekender hot-spots cool off when the weather gets cold, second homes in Pawling tend to be used year-round since the 90-minute train ride from Grand Central makes it a quick getaway destination.


Pawling’s generational shift means that there are currently a lot of options within the village, ranging from condos and townhouses priced at around $180,000 to multimillion-dollar historic homes on prestigious Quaker Hill Road. With a median home value of $319,000, there’s something available to fit almost any budget and style; however, it should be noted that Pawling’s taxes tend to be high. A pair of spacious four-bedrooms built in 2005 recently went on the market for $499,000 and $550,000; meanwhile, another four-bedroom house built in 1800 was available for $825,000. Even those looking for bargains will come away happen: The price of a three-bedroom house from 1978 built on the shores of Sunset Lake was $242,500.

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