Spotlight on Westchester :: Chappaqua

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We all love our own little cozy corners of Westchester. There are so many things to do and see, places to eat, and parks to visit. Who doesn’t love exploring the county and “finding” the kid-friendly gems! We are spotlighting some of those awesome places so that other moms can take advantage and get a glimpse into the awesomeness that is Westchester! Read all posts in our Spotlight on Westchester Series.

While Chappaqua is often known as “the leafy hamlet” (due to how green it is, literally and figuratively), the hamlet is shockingly down to earth. Family-oriented, educated, artsy, and social justice-minded, there are plenty of reasons Chappaqua is so desirable (did I mention the top-ranking school district?). Here is why you’ll love living in and visiting the New Castle hamlet of Chappaqua.

What to Do

Chappaqua offers tons of programming and family-friendly activities throughout the year. Here are some of the notable mentions.

Chappaqua Children’s Book Festival: The Chappaqua Children’s Book Festival is a beloved community staple. Each autumn, families descend downtown to meet authors, listen to readings, purchase books, meet characters, and celebrate children’s literature. Many families come from well out of town for the occasion.

Memorial Day Parade: If you live anywhere in the tri-state area, you probably already know about the New Castle Memorial Day Parade. This grand event normally starts near 120/King Street and 117/North Bedford Road with a memorial service. The parade then travels into town via King Street. Previous years included attendees such as the Clintons (but you probably already knew that, didn’t you?), and the occasion serves as both a joyous welcome for the summer and a time of reflection for those who have lost their lives serving our country. There is typically a celebration at the end of the parade route, near the train station.

Chappaqua Performing Arts Center: Chappaqua Performing Arts Center offers programming and theater presentations in the heart of Chappaqua. The beautiful theater is located on the revitalized Readers Digest campus (now also home to a large shopping plaza and apartment complex). While, for the time being, no performances are taking place (due to current circumstances), we look forward to welcoming shows back ASAP.

Chappaqua Farmers Market: While smaller than neighboring Pleasantville’s (and only open during warmer months), the Chappaqua Farmers’ Market is still worth visiting.

Chappaqua Library: Chappaqua Library offers traditional programming for the family and just renovated their children’s room. However, they also offer tons of exciting, kid-friendly programming. Think, opportunities for kids to explore big trucks, STEM workshops, LEGO Club, Chess Club, Teen Current Events meetups/discussion, movies, grab and go crafts, and more! We knew Chappaqua Library was an incredible community resource long before moving to the area, because the programming is so popular! Many programs do require prior registration, and fill up fast, so be sure to keep an eye out (if you live in the community, you’ll also get mailers, which are super helpful)

Shopping: As one would expect in a community like Chappaqua, there are plenty of nice boutiques downtown. And don’t forget to stop by famed Scattered Books! They have a wonderful curated selection, plus plenty of great options for kids. Don’t forget to say hi to the resident bunnies before you leave!

Halloween Downtown: Every Halloween the local businesses in the downtown district give out candy to excited, costumed kids from the community. Having lived in the city for many years, the event reminds me some of how trick or treating worked in NYC, but with a distinct and quaint small town vibe. Conjure up an image of some little New England village (Stars Hollow from Gilmore Girls, maybe?) and that is the vibe. It isn’t quite as big an affair as neighboring Byram Hills’ trick or treat event, but it is still a good stop, especially if you have very small children who can’t walk longer distances

The author’s husband and child, Halloween 2019 , in downtown Chappaqua

Get Outside

Gedney Park offers hiking, an excellent playground, and one of the best public sledding hills in the county. People also often fish in the pond. The park also periodically hosts events.

Pinecliff Sanctuary is a great stop for families with small children. The short boardwalk offers ample opportunity for exploring nature, and includes lots of information about native floral and fauna. It is also ADA compliant, and specifically, is wheelchair accessible. If you have a disability (invisible or not), I need not tell you how incredible that is. Though it absolutely shouldn’t be something that sets parks and preserves apart, it sadly still does. Parking is a bit tight as the preserve is located in a residential neighborhood, but it is always quiet, making it a perfect spot during times where social distancing is necessary. I hope including it in this guide doesn’t spoil this quiet hidden gem.

Glazier Arboretum offers a wide range of very easy and easy trails for people of all ages (and dogs!). Centered around a lovely pond and wetland off Whippoorwill Road on the southeast side of town, trails fan out and over hills through wooded terrain. It is easily one of my favorite places to take my toddler for mini hikes, but it is enjoyable for kids of all ages.

Glazier Arboretum, Chappaqua [Photo Credit Erin Kirby]
Glazier Arboretum, Chappaqua [Photo Credit Erin Kirby]
Just north of Glazier Arboretum, Whippoorwill Park offers slightly more challenging trails. Covering wooded terrain, wetlands, ponds, and streams, the park is perfect for a day out with the family. It is also very close to downtown, so it is easy to grab a coffee, juice, or a bite to eat before or after

Where to Eat

Speaking of eating, Chappaqua some excellent spots to do so! Here are some of my family’s favorites, as well as establishments our neighbors love!

  • Waka Asian Bistro: My husband and I love their sushi, lo mein, and fried rice!
  • Quaker Hill Tavern: Quaker offers solid pub favorites and their burgers are quite good!
  • Bagel Emporium: One of the best places in Westchester to grab a bagel, in case you didn’t know! After living in NYC for nearly a decade, bagels have become a necessity, so having Bagel Emporium in the community is a definite plus!
  • Pizza Station: Pizza Station offers great pizza options, but also has amazing salads!
  • Susan Lawrence Gourmet Foods: Stop in for coffee, a meal, baked goods, or order takeout! Plus, Susan Lawrence offers cooking classes, catering, and more.
  • Le Jardin Du Roi: This French bistro is frequently listed as a town favorite!

    Where is your favorite spot in Chappaqua?

    To read all posts in our Spotlight on Westchester series, click here.

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Erin is the mother of one sweet, rambunctious toddler and wife to a talented chef. Professionally, she is a former special educator and preschool teacher, and is currently a cognitive neuroscience researcher and Ph.D candidate in Cognitive Science in Education with specializations in neuroscience, cognitive development, and neurodiversity/autism. She holds masters degrees in cognitive science, and neuroscience in education, from Teachers College, Columbia University, and undergraduate degrees in special education (with an additional concentration in elementary education and a minor in English) and early childhood education. As the wife of a chef, food is a huge part of her family culture, and she enjoy both cooking and baking. Some of her other hobbies include hiking, traveling, jogging, meditation, animal rescue, playing piano and guitar, crafting, reading, and of course, writing. You can follow her parenting journey and pick up tips on great kids activities here on Westchester Moms Blog, as well as her website (, Facebook, Instagram, and Pinterest accounts.