Discover Westchester: Living in Chappaqua, NY

Feb 7, 2025

When you close your eyes and picture the suburbs, Chappaqua, NY might just be the town that comes to mind.

With hundreds of acres of green space, a vibrant downtown filled with unique, mom-and-pop shops, and spacious homes built on large lots and newly constructed, high-end townhomes, this sought-after community in Westchester County is a must-see. Plus, the hamlet is just 30 miles north of Manhattan if you’re looking for reasons to move to Chappaqua.

Here are five of our favorite things about living in Chappaqua, N.Y.:

1. Chappaqua is Family-Friendly

If you dream of raising your children in a small town, you may want to consider living in Chappaqua in Westchester County. The hamlet is home to three neighborhood elementary schools, two middle schools, and Horace Greeley High School. The high school, with a 10:1 student-teacher ratio, was named one of the best high schools in the country by U.S. News & World Report.

Story times, concerts, and kids’ movies are always on the calendar at the Children’s Room at the Chappaqua Public Library. Every fall, the hamlet hosts the annual Chappaqua Children’s Book Festival where kids can meet the authors of their favorite stories. The whole family can also browse the shelves at Scattered Books, an independent bookstore in the hamlet’s commercial district. 

2. Chappaqua is a Nature Lover’s Paradise

You don’t have to go far to explore the great outdoors in Chappaqua. Whippoorwill Park is a 167-acre escape with a pond and well-marked trails for hiking and running. Gedney Park has a series of interconnected, dog-friendly trails that loop around a playground, ball fields, a fishing pond, a sledding hill, and a 9/11 memorial. 

Bird lovers flock to the glorious Pinecliff Audubon Sanctuary at the north end of the hamlet to spy green herons, ospreys, ruby-throated hummingbirds, woodpeckers, owls, and other winged creatures.  

For plenty of outdoor fun, Recreation Field hosts car shows and a free summer concert series. There are several private swim and tennis clubs, like Chappaqua Swim & Tennis Club and Birchwood Swim & Tennis.

3. Chappaqua Offers a Strong Sense of Community

The hamlet encompasses less than one square mile, while the total population hovers around 3,000 residents. But what Chappaqua lacks in size, it more than makes up for in community spirit. 

Residents get a taste of the sweet life every June during the annual Strawberry Festival. You can run into your neighbors for live music, kids’ games, a petting zoo, and, of course, strawberry shortcake. Since opening in 2017, the Chappaqua Performing Arts Center has cemented its spot as a community hub. The year-round schedule features kid-friendly shows, live music, cultural performances, and comedy acts.

4. Chappaqua is a Foodie Paradise

Foodies will find plenty to feast on at Chappaqua’s restaurants. Choices include the popular French-American Le Jardin Du Roi, the historic Crabtree’s Kittle House Restaurant and Inn, serving inventive New American fare on its bucolic property, and the beloved Bobo’s Cafe at the train station, where commuters and locals sit down for freshly brewed coffee and tasty breakfast and lunch options. 

On Saturdays from May to December, the train station also hosts a farmers market that sells locally sourced fruits and vegetables, prepared foods, baked goods, fish and meats, spirits, and more.

5. All this—Plus an Easy Commute to New York City

Westchester’s top suburbs also offer convenient commuting options. While Chappaqua may feel like it’s a world away from the hustle and bustle of Manhattan, the hamlet is just a 50-minute train ride to Grand Central Terminal on the Metro-North Railroad. Parking is available at the Chappaqua train station, but a parking permit is required. 

More Westchester Towns We Love

Curious about what other towns Westchester has to offer? Take a peek a few of our favorites: 

For more insights, visit SJ’s New York City suburbs section and the New York City blog page on our website.

Ready to start your suburban search? Schedule a free initial strategy call.

Photo Credit: Ajay Suresh

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