Pleasantville, NY Road Trips

Before being incorporated in 1897, the land creating the village of Pleasantville was settled by communities of Lenape Native Americans. After being incorporated as a stop on the New York and Harlem Railroad in 1846, the soon-to-be village flourished due to being close to New York City. Pleasantville is a charming town centered around its train station in the center of downtown. While offering all the amenities of a bigger city, the village has been able to keep its small-town feel, making it a popular option in the Lower Hudson Valley for families looking to raise their children. Pleasantville is also home to a secondary campus for Pace University, which allowed the village to be youthful in spirit. Pleasantville is the longtime mailing address for Reader's Digest magazine, even though its headquarters is in nearby Chappaqua. Much like the rest of the lower Hudson Valley, the village experiences hot, humid summers with highs upwards of 80 °F (high 20s Celsius), and cold winters with daytime highs around 40 °F (low single digits Celsius). While snow is common, there is usually no snowpack in the winter due to the freeze-thaw cycle.

1 Jacob Burns Film Center, 364 Manville Rd, ☏ +1 914-747-5555. The nonprofit center five-screen cinema housed in a Spanish mission-style theater shows over 400 curated series, international films, and documentaries every year, and is one of the leading suburban art houses in the United States. They also offer over 100 special events every year, including talk series with filmmakers, actors, authors, and activists, and live music performances. $16 for a general admission ticket with a $1.75 online surcharge. (updated Nov 2024) 2 St John's Episcopal Church, 8 Sunnyside Ave. Gothic Revival church designed by architect Charles A. Hoag and constructed in the early 20th century using rough-hewn granite blocks, with a limestone-like cast stone trim. On the National Register of Historic Places since 2017. (updated Nov 2024) 3 Marmaduke Forster House, 415 Bedford Road. A historic house that was built in 1785 as a farmhouse. Over its lifetime, it has been remodeled in a Gothic Revival style and Queen Anne style, keeping some of its past characteristics during renovations. Now on the National Register for Historic Places, the house functions as office space. (updated Nov 2024)

As one might expect with its many beautiful tree-lined streets and rolling hills, Pleasantville is home to a wide variety of outdoor activities within a ten minutes drive from downtown. The town is home to numerous small ponds and lakes, many of which are frequented by local middle and high school boys catching fish in the summer and playing ice hockey in the winter, but also great for a quiet picnic in the spring or fall. 1 Rockefeller State Park Preserve, 125 Phelps Way. Dawn-dusk. The park is the former property of the Rockefeller family, who since 1983, have been slowly donating the land to New York State to be preserved and safeguarded. The preserve offers 45 miles of scenic carriage roads that were originally used for carriage driving, but are now are designated as multipurpose trails, although horses are still common sights along the trail. Just make sure to be on the lookout for horse poop while walking. $6 per car, $15 for a horse. (updated Nov 2024) 2 Graham Hills Park, Bedford Rd (Route 117) (A mile southwest of downtown, across from Pace University), ☏ +1 914-231-4500. 8am-dusk. Situated on 400 acres of wooded terrain in between the Saw Mill River and Taconic Parkways, the park has five miles of single-track mountain biking trails geared towards experienced mountain bike riders. The trails are rocky and challenging, helmet is required, and additional protection is recommended. There is a parking charge. (updated Nov 2024) 3 Opperman's Pond Park, 3 Lake Dr (Half a mile southwest of downtown on Bedford Rd). Dawn-dusk.

If there is one thing that Pleasantville has down pat, it's the food. Although a small village, Pleasantville is home to many restaurants, many among the most popular in central Westchester County. Within downtown, the independent food culture becomes apparent; there is no fast-food chains (other then the Dunkin' and the Starbucks across from the train station). During the summer, many of the eateries on Wheeler Ave and Washington Ave set up streetside dining. Something that the village seems to do just right is delis; every corner of the village there seems to be one, and you cannot go wrong with any of them. Some common classics in the Pleasantville delis include the homemade chicken noodle soup, the Italian sandwich, and a classic bacon, egg and cheese sandwich on a roll. The village is also home to many different New York style pizzeria institutions that have been open for decades; every local has their favorite shop, but they are all great slices. Although dollar slices no longer exist, the value you get at the pizzerias make up for the price, with even the hungriest customers sometimes struggling to eat two slices. 1 On's Chinese Kitchen, 475 Bedford Rd, ☏ +1 914-741-6277. Small, no frills American-Chinese restaurant. Small indoor seating area. Fast service, no cards accepted. Minimum order for delivery is $28. Parking in front of the store is metered, but around the corner on Cooley St. is free. $10 for a lunch special, $10-15 for dinner. (updated Nov 2024) 2 Lucio's Pizzeria, 76 Washington Ave, ☏ +1 914-741-9200. M-Sa 10AM-10PM, Su 10AM-9PM.

There are additional bars in the county seat, White Plains, a 15 minute car or train ride south. 1 Foley's Club Lounge, 479 Bedford Rd (5 minutes west of the train station), ☏ +1 914-741-2079. M-Su 11AM-2AM. Small laid-back locals' bar with the standard fare of drinks. Has a large bar food menu that is reasonably priced and large. Beer $5-$10, mixed drinks starting at $10, bar food $10-$15. (updated Mar 2025) 2 Lucy's, 446 Bedford Rd (2 minutes from the train station), ☏ +1 914-747-4740. M-Su 4PM-midnight. Retro themed establishment with live music every weekend and a full bar. Always busy on Friday nights and weekends, and an affordable food menu. Drinks from $5, bar food $10-$15. (updated Mar 2025)

The closest hotels are in Tarrytown (15 minutes southwest by car) and White Plains (15 minutes south by car or train)

Westchester County Airport(HPN IATA), is 15 minutes south in the city of White Plains. The airport receives regular service by five airlines and offers direct service to over ten cities on the eastern seaboard in addition to Puerto Rico and Bermuda. The airport offers many rental car options. Stewart International Airport(SWF IATA) is 40 miles northwest of Pleasantville in the town of New Windsor. While a nice alternative to the congestion of the three main airports of New York City, public transportation is scarce, time-consuming and expensive. The airport is served by three airlines, and offers non-stop flights from Reykjavik and cities in Florida and South Carolina. The airport offers several rental car options. Newark Liberty International Airport (EWR IATA), John F. Kennedy International Airport (JFK IATA), and LaGuardia International Airport (LGA IATA) are the three major international airports in the New York City metro area and offer service to just about anywhere around the world. If you are a visitor to Westchester County, you will most likely fly into one of these three main airports. While the central hub for downstate New York, it can be a real headache to get transport to Pleasantville from these airports, and it is recommended to rent a car at the airport from one of the many car rental companies. While taxi service is possible from the airports, it is not recommended unless in a pinch, as New York's iconic yellow cabs tack on exorbitant surcharges for trips into Westchester County.

Downtown Pleasantville is not very large, and with free parking in downtown being nonexistent, you are better off walking. While paid parking is available in most parts of downtown, spots are narrow, require difficult maneuvers, or have confusing signage. Meters do not have to be paid on Sundays and at nighttime, and usually cost around $1 per hour. Free parking is available on most streets a quarter mile to half a mile in any direction from downtown, with the most accessible parking being northeast of town center. Downtown and the surrounding areas within half a mile of downtown are relatively safe for pedestrians, with sidewalks in good order, and plentiful crosswalks with good signage for drivers.