Welcome to Chappaqua
Westchester County’s smallest town with the biggest draw
Although Chappaqua is one of the smallest towns in New York’s Westchester County, there is no shortage of love and community pride here.
The hamlet traces its name to the Native American tribes of the Mohegan Confederation who farmed the land in New Castle. The area now known as Chappaqua was called Shepequa, which referred to the plentiful local water sources, according to the
New Castle Historical Society. Horace Greeley, the renowned journalist and a founder of the Liberal Republican Party during the 1800s, owned a home in Chappaqua that is still there today.
Chappaqua, despite the influx of well-to-do Upper West Siders and Brooklynites in the last two decades, has retained a small-town rural feeling. Even though public figures like Bill and Hillary Rodham Clinton and Ben Stiller live in Chappaqua, it has retained its down-to-earth, family-oriented feel.
What to Love
- Well-known small town for Manhattan’s elite
- Quaint country living with a luxurious note
- Friendly, hospitable neighbors and a welcoming charm
- Strong parent community that is very involved in the PTA
People and Lifestyle
With just under 1,500 residents, most neighbors in this close-knit community know each other by name. The main drag in the heart of the hamlet, South Greeley, is lined with mom-and-pop shops that close their doors in time for everyone to get home for dinner.
While celebrities and notable people live in town, “Chappy” residents are down-to-earth and always hospitable to one another. They care deeply for their town, their children, and the many local businesses and organizations.
Dining, Entertainment, and Shopping
Chappaqua is truly a foodie’s paradise with fantastic offerings and locally owned businesses. Any local will tell you that the town’s most famous eatery is Le Jardin Du Roi, which serves up an authentic French cafe menu alongside a full bar and barista counter. Crabtree Kittle House was built in 1790 by local farmer John Kittle and has continued to serve farm-to-table fare since then. Pizza Station and Old Stone are great family spots for wood-fired pizza, while Ibiza is a buzzy Mediterranean restaurant in the center of town. For great grab-and-go meals, Bobo’s Cafe and Rocky’s Deli are local favorites. Try Lange’s Little Store and Delicatessen for a taste of old-school small-town charm.
Chappaqua’s amazing farmers market, where you’ll find everything from local beer to hot sauce to dumplings, draws hardcore foodies from all over Westchester. Even the local commuter train station cafe boasts a seasonal menu.
Things To Do
Residents often meet up at Gedney Park for a pickup game of soccer, and kids congregate here to play their own soccer games on the weekends. The Chappaqua Swim and Tennis Club is a popular place to become a member for the summer seasons, while the Chappaqua Library is a well-appointed town gathering space to spend an afternoon with kids.Schools
The Chappaqua Central School District is perhaps the best in Westchester. In 2020, U.S. News & World Report ranked Chappaqua’s three elementary schools in the state’s top 75 and its two middle schools in the top 20. It’s home to the prestigious Horace Greeley High School, which consistently ranks as one of the best public high schools in the country. It topped Best College’s national ranking in 2015 and finished in the top percentile of U.S. News & World Report’s 2020 rankings. “Chappy” parents are renowned for having a strong PTA and are active in the school’s offerings.
