Chappaqua is a small suburban town. Most people living here are living here because of its elite school system. The town is filled with relaxing things to do and historical things to see but if you are looking for night life this is not the place.
Westchester County Airport, 240 Airport Road, White Plains, +1 914 995-4860 (airlines), . The closest airport, about 10 minutes drive. Rental cars are available.
Stewart International Airport, 1180 First St, New Windsor, +1 845 564-2100, . Another alternative to the congestion of the 3 major airports, but at present offers few direct flights.
Newark Liberty International Airport, Newark, New Jersey, , John F. Kennedy International Airport, and LaGuardia Airport: The three major international airports in the New York City area offer service to just about anywhere. Westchester-based taxi and livery cars offer regular service to and from the three internationals from most areas of the county. New York City yellow cabs will take to you Westchester in a pinch, but the fares can be exorbitant. If staying in Westchester, ask if your hotel offers shuttle service.
New Castle Historical Society, 100 King St, +1 914 238-4666, . The society is located in the former home of Horace Greeley, publisher of the New York Tribune. See the desk at which Greeley wrote editorials for the Tribune. T, W and Th 1PM-4PM and Sa 1PM-4PM. Museum is also open by appointment. Closed Saturdays during the month of August.
Quaker House/Chappaqua Friends Meeting House, 400 Quaker St. Established in 1753 by the Quakers that founded Chappaqua the Quaker meeting house used to be used as a religious center for the community to meet and discuss issues. Today the house still holds meetings and hosts a preschool program. Tours are available but you can just walk around if you please. One of the older cemeteries in Westchester is also located here.edit
Bill Clinton's house, 15 Old House Lane. This is private property so mind your distance but you can drive down the street and take a look at where the ex-president is living.edit
Gedney Park. Containing 126 acres of park ground Gedney park has a wide range of activities for all ages. There is a large playground for kids and benches next to the duck pond for eating and relaxing. The park has three hiking trails, the terrain ranges from flat to hilly and rocky. Towards the back of the park there are two baseball fields and a soccer field usually being used by a rec league. There is also a 9/11 memorial at the park which consists of two fountains, benches, and two pieces of metal from the towers. Located on route 120/133 ½ mile from Millwood. Website (trail maps located here) .
Glazier Arboretum, Off Whiporwhill Rd. A 47.6 acre arboretum consisting of meadow lands, wooded areas, a pond, and swamp lands made walk able due to a wooden walkway. Easy hike, little to no hills, great scenery, easy enough for kids.
Skate Park, (in the commuter lot at the Chappaqua train station), . Skate park for skateboarders and roller bladders. Helmet, knee pads, and elbow pads must be worn. Street skating (no mini ramp or half pipe) the park has a roll in, Three quarter pipes, and a large box in the middle with rails. Children under eighteen must have a waiver signed by their parents. Pads and board must be supplied by yourself. Lessons available. Day pass for residents $5, non residents $7.
Whippoorwhill Park Large wooded area filled with hiking trails. After a couple minutes of walking you really feel like you are in the middle of nature. Information signs posted about native trees and animals. Tree's marked so you don't get lost. For experinced Hikers.
Jacob Burns film center, 39 Washington Ave, Pleasantville (at the centre of the town over from Chappaqua), +1 914-747-5555, . Non profit movie center and education center. Films shown are generally independent, artsy, films. A change of pace from the films normally seen in theatres.
Mt. Kisco movie theatre, 144 W Main St, Mt Kisco (town over from Chappaqua), +1 914-660-7400, . Showing movies simultaneously with the movie theatres elsewhere, Mt. Kisco movie theatre consists of 8 screening rooms. General admission $11, Children $8.25.
Grand Prix Racing, 333 North Bedford Road, ☎ 914-241-3131, . Looking for an extreme thrill? Check this out—indoor Go Kart track activities for all ages as they have an Arcade and a resaurant. edit
Mt. Kisco Golf Club, 10 Taylor Road, ☎ 914-666-2116. Country club but call ahead and get a tee time. Quick greens, great landscaping, 18 hole course. Caddies and carts available. Located in Mt. Kisco (town over).edit
Langes Deli, 382 King St, +1 914-238-3553. Bill Clinton’s favorite and a local institution Lange’s deli in Chappaqua has a wide selection of food and offers something for everyone. Very good subs and high quality food subs are generally between seven to ten dollars. Eating area with tables and television in deli.
Pizza Station, 88 South Greeley (downtown), +1 914-238-1400. Italian cuisine from Pizza to pasta to salads. Casual atmosphere, great for kids as them making noise is not an issue, area to sit and eat within the restaurant. Delivery available.
Mario’s Pizza., 13 King St, +1 914-238-3858. Italian Cuisine. Casual atmosphere with area to sit down and eat.
Waka Asian Bistro, 95 King St, +1 914-861-2727. Japanese Cuisine. Formal setting with wait staff. Great Japanese food, well known locally for the sushi (the spicy tuna is some of the best in Westchester).
Villarina’s, 27 South Greeley Ave, +1 914-756-9512. Custom wraps and Italian market. Wide variety of wraps and sandwiches which are very good. Deli meat also available along with homemade pasta.
Rocky’s Deli, 235 Saw Mill River Rd, Millwood, +1 914-941-2165, . In Millwood since 1967 Rocky’s is a local favorite due to the wide variety and good quality of food, friendly staff, and the fact that it is open 24 hours a day. No sit in area to eat though, local’s usally eaten on the curb outside of the deli or in their cars. You can also just bring the food back home. If you’re starving at three A.M this is the only place that will be available. They do not accept credit cards but an ATM is located inside.
Quaker Hill Tavern, 61 North Bedford Road, . Restaurant and Bar, crowd usually consists of people in their 30's to 50's. Family setting in the afternoon but not later at night. Tables inside and outside.edit
Kittle House, 11 Kittle Road, +1 914 666-8044, . Originally an 18th-century barn, the Kittle House was converted into a mansion some 100 years later. It now has 12 rooms with king- or queen-sized beds, private baths, and cable television, and price includes breakfast.