Neighborhood Guide: Chappaqua

Tucked into the east bank of the Hudson River just 30 miles north of New York City, Chappaqua is a quaint town nestled in northern Westchester county. Combining the best of rural and city living, this bucolic town has a train station with express access to Manhattan—but also has all of the necessities you’d ever need. Chappaqua has a beautiful blend of the best of all worlds. It boasts the natural beauty of lush surroundings, the convenience of proximity to all Manhattan and an endearing sense of community.

Discover the best the town has to offer through the eyes of a few experts: Douglas Elliman agents and Chappaqua residents Nancy Shafiroff, Gladys DiSisto and Gita Kinney.

What to Do 

Though it may seem the lure of bustling Manhattan would draw residents away and into the city, Chappaqua itself has everything you could ever need. Downtown Chappaqua features a wide variety of local merchants including the fashionable clothing stores as well as a restaurants, galleries, salons and other businesses. According to locals, these are the best of the best when it comes to activities in this picturesque town.

Farmer’s Market

Bringing locally grown food to the Chappaqua community, the Farmers’ Market takes place every Saturday at the Chappaqua train station from 8:30 am until 1 pm. With everything on offer from jams to biscuits and pickles and produce, the market works to raise awareness of sustainability of the importance of eating local.

 Chappaqua Performing Arts Center

Recently renovated, the 425-seat Chappaqua Performing Arts Center has a mix of local, regional and national showcases to provide a diverse offering. With guest speakers, theater and concerts all on their upcoming calendar, it is a cultural institution in the Westchester area.

Gedney Park

Pretty spot. #roadslikethese #exploreny #optoutside #ridewithgps #fallfoliage

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Gedney Park is a beloved community gethering spot consisting of 126 acres, with hiking trails, ballfields, a dock pond and a new state of the art playground. It’s the perfect place for a hike, to relax on the beach or meet up with your neighbors. Just down the road from Gedney Park you can also access the North County Trailway, a multi-use scenic paved path, once a part of the New York Centrail Railroad track, where residents can walk, jog, bike ride and roller blade.

Where to Eat

Chappaqua isn’t lacking when it comes to restaurants. With every cuisine imaginable on offer from Mexican to Japanese to French, you can’t go wrong. These top-tier restaurants are a few favorites from locals in the know.

Crabtree’s Kittle House

Winner of the 2018 Best of Westchester award for Best Private Dining, this charming space has a storied history spanning over 200 years. Beginning as a farm before becoming a school and now an award-winning restaurant and wine cellar, Crabtree Kittle House is serving up some of the best farm-to-table, sustainable cuisine in the area.

Jardin Du Roi

OYSTERS are $1.00 each – tonight at #lejardinduroiinchappaqua !!! #bluepoints #buckashuck

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Situated in downtown Chappaqua, this bistro is serving up French classics alongside award-winning barbecue. Escargots, moules frites and fromages et fruits can be found on the traditional menu that is rounded out with rotating daily barbecue specials from Q Haven BBQ. Enjoy brunch or dinner on their beautiful back patio for picturesque al fresco dining during the warmer months.

Aesops Fable

This restaurant boasts an eclectic seasonal menu selection to suit every taste and craving. Their wood-fired pizza is a crowd favorite, with classics like Margherita or house special pies like the Zucca with homemade ricotta, garlic, summer squared, parmesan, chive and rosemary. Also a popular brunch spot, Aesop’s Fable has a wine garden seating and food sourced from local farmers for a restaurant that is both delicious and locally-inspired.

Where to Live

31 Aldridge Road

Price: $949,000

4 Bedrooms | 2.5 Bathrooms

117 Random Farms Drive

Price: $1,290,000

5 Bedrooms | 4.5 Bathrooms

5 Woodbridge Court

Price: $1,740,000

4 Bedrooms | 5.5 Bathrooms

Discover more stunning homes in Chappaqua.

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