Discover Westchester: Exploring Chappaqua

Jun 26, 2024

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

With its hundreds of acres of green space, vibrant downtown, homes on spacious lots, and a calendar of annual events like the Strawberry Festival, this sought-after community 30 miles north of Manhattan is a must-see. Here are five of our clients’ favorite things about about life in Chappaqua:

#1. Family Friendly

If you dream of a small-town upbringing for your kids, Chappaqua delivers. Chappaqua is home to three neighborhood elementary schools, two middle schools, and Horace Greeley High School—named one of the best high schools in the country, with a 12:1 student/teacher ratio. Story times, concerts, and kids’ movies are always on the calendar at the Children’s Room at the Chappaqua Public Library, and every fall, the town hosts an annual children’s book festival where kids can meet the authors behind their favorite stories.  

#2. Close to Nature

You don’t have to go far to explore the great outdoors in Chappaqua. Whippoorwill Park is a 167-acre escape with a beautiful  pond and well-marked trails for hiking and running, while 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 town to spy green herons, ospreys, ruby-throated hummingbirds, woodpeckers, owls, and other winged creatures.  For a little less nature but plenty of outdoor fun, Recreation Field hosts car shows and a free summer concert series. While there’s no town pool, there are several private swim and tennis clubs, like Chappaqua Swim & Tennis Club and Birchwood Swim & Tennis.

#3. Strong Sense of Community

The total population, hovering around just 3,000 people, may be small, but Chappaqua makes up for its small size with an outsized spirit of community. Residents get a taste of the sweet life—literally!—every June during the annual Strawberry Festival, when residents gather 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, with a year-round schedule that heavies up on kid-friendly shows, live music, and comedy acts.

#4. Foodie Paradise

Foodies find plenty to feast on at Chappaqua’s restaurants, including popular French-American Le Jardin Du Roi, the historic Crabtree’s Kittle House Restaurant serving inventive New American fare, and the beloved Bobo’s Cafe at the Metro-North station, where commuters and locals sit down for fresh brewed coffee and tasty breakfast and lunch options. On Saturday from May-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

While Chappaqua may feel like it’s a world away from the hustle and bustle of Manhattan, it’s just a 50-minute train ride to Grand Central on Metro-North. Parking is available at the Chappaqua train station, but a parking permit is required. 

Looking for your forever hometown? Connect with a Suburban Jungle Strategist today to get started on your search. 

Photo Credit: Ajay Suresh

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