Pleasantville is a village in Westchester County, New York. Pleasantville is the longtime mailing address for Reader's Digest, even though their headquarters is actually in nearby Chappaqua.

Get in

By plane

• Westchester County Airport, 240 Airport Road, White Plains (New York), +1 914 995-4860 (airlines). The closest airport, about 15 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. Allegiant Air, American Eagle, and JetBlue operate flights from Florida and Philadelphia (Mar 2021).
• 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.

By car

• Pleasantville is easily accessible from the Saw Mill River Parkway, which runs along the village's western flank, connecting with the Taconic State Parkway to the north (to Albany and the I90 east-west portion of the Thruway system) and the Henry Hudson Parkway into New York City.

By train

• Metro-North Railroad - Harlem line, . Express service between Pleasantville station and New York City's Grand Central Terminal is about 35 minutes. Local service is available between other Metro-North commuter stations. On-board train fares are subject to a stiff surcharge, so buy your tickets at the station or at the vending machines located on the platform.

See

• 1 Jacob Burns Film Center, 364 Manville Rd, ☏ +1 914-747-5555. The nonprofit center shows independent films, documentaries, and classics. 

Do

• 1 Graham Hills Park, Bedford Rd (Route 117), ☏ +1 914 864-7275. Mountain biking. Parking fee, helmet required, trail map is available online. Five miles of trails through 431 acre county park, geared toward riders with some experience. Park is in the middle of the county at the junction of the Saw Mill River, Taconic, and Sprain Brook Parkways. 
• 2 Prospero Winery, 123 Castleton St, ☏ +1 914-769-6252, info@prosperowinery.com. M–F 8AM–5PM, Sa 9AM–2PM, closed Su. Produces wine from grapes sourced across the country. (updated Apr 2021)
• 3 Farmers' Market, 10 Memorial Plaza (off Manville Rd, Metro-North parking lot). Sa, 8:30AM-2PM, June to mid December. 

Eat

Mid-range

• wood and fire, 59 Marble Ave, ☏ +1 914 747-2611. noon to 10pm. Pizzeria. (updated Apr 2023)

Go next

Pleasantville is in central Westchester County, and surrounded by Chappaqua to the north and west and Briarcliff Manor to the west. Pleasantville is also close to New York City, and is less than 30 miles north of Manhattan.

Routes through Pleasantville

Katonah ← Chappaqua ←	N  S	→ Elmsford → New York City
Amenia ← Chappaqua ←	N  S	→ White Plains → New York City