Chappaqua with Kids: 30 Things to Do for Westchester Families

Chappaqua is a quaint hamlet located near the center of Westchester in the town of New Castle, just about 30 miles from Midtown Manhattan. Known for its charming neighborhoods, the village maintains a peaceful New England feel, with rolling hills and historic homes and barns.

Chappaqua offers a wealth of public parks, protected wetlands and wildlife sanctuaries with hiking trails, well-maintained playing fields, courts and other facilities for tennis, soccer and skating. It also boasts a walkable village featuring family-friendly restaurants, shops and a farmer’s market. There's no shortage of events or things to do here during the year, and we've gathered our top 30 things to do in Chappaqua with kids.

1. Join the knitting club, visit drop-in Saturday story time, catch a concert, and enjoy songs, stories and sensory activities at the Chappaqua Library.

2. Bring home local, farm-fresh produce, eggs, meat and mouth-watering baked goods; enter a baking contest; and catch cooking demonstrations at the year-round Chappaqua Farmers' Market.

3. Listen to your favorite authors read excerpts from their books at the annual Chappaqua Children’s Book Festival.

4. Drop your children off at World Cup Gymnastics for Kids Night Out on select Saturdays while you enjoy a date night.

5. Satisfy your sweet tooth with ice cream and then peruse row after row of nostalgia candy, and shelves packed with toys and gifts at Hall of Scoops.

Hall of Scoops

6. Learn about local history through exhibits, lectures and publications at the New Castle Historical Society.

7. Indulge your love of nature with a visit to the 126-acre Gedney Park, where you’ll find hiking trails, a pond, and a little covered bridge over a creek and into the playground area.

8. Don a costume and make your way to the annual Ragamuffin Parade and Halloween Carnival.

9. Browse through an amazing selection of philanthropic, all-organic, animal-free or fairly traded clothing lines and accessories at hip-kid.

10. Help raise money to fight childhood hunger at The Great Chappaqua Bake Sale.

11. Enjoy one of the free Chappaqua-Millwood Chamber of Commerce Summer Concerts held at The Gazebo on Recreation Field.

12. Take a holiday window walking tour, create arts and crafts and meet Santa at the annual Winter Festival.

13. Attend a workshop at Scattered Books with your kids where they can make things like Minecraft collages, American Girl journals and holiday cards.

Scattered Books

14. Admire the wide selection of artworks, gourmet foods, jewelry and accessories at the annual Craft & Gift Fair.

15. Bring the whole gang to Quaker Hill Tavern for Kids Eat Free Night on Mondays.

16. Grab a blanket and some popcorn and enjoy an outdoor family-friendly movie at Millwood Park.

17. Hit up the annual three day Sidewalk Sale for bargains, samples and discounts.

18. Get moving at the yearly Think Fit For Kids Family Fitness and Fun Festival with 3D Archery, Mobile Archery, Carnival Games, Zumba, Basketball and more.

19. Pick out your favorite piece of art that your kids have made and have Doublevision Photographers make a T-shirt out of it.

20. Pop in to Sherry B Dessert Studio and customize your own cookie ice cream sandwich.

21. Enjoy a day of games & prizes, bounce castles, music, BBQ and, of course, the strawberry shortcake at the annual Strawberry Festival.

22. Go for a hike at Glazier Preserve. 

Chappaqua Farmers' Market

23. Camp out for the night or organize a friendly neighborhood softball game at Whippoorwill Park.

24. Take a yoga class with your teen at Breathe Pilates and Yoga.

25. Pick out a new bike at the family-owned Julio Bicycles.

26. Do some one-stop clothing shopping for the entire family at Squires Family Clothing & Footwear. 

27. Skip cooking and eat Mario's wood-fired pizza. 

28. Eat Local! 

29. Get some classic deli-sandwich staples at Lange's Little Store. 

30. Babies as young as 8 weeks old can grow a love of music at the Amadaeus Conservatory of Music. 

This originally published in 2016 and has been updated for 2017. 

All photos taken by the author.