Overview
Pleasantville is a village in Westchester County, New York. Downtown Pleasantville is very walkable, and has many independent restaurants, boutique shops, and grocery stores. The Jacob Burns Film Center, in the Rome Theater in downtown, was one of the first movie theaters in Westchester, and focuses primarily on independent, documentary, and world cinema.
3 sights · 10 things to do · 10 places to eat · 2 bars & cafés
Updated from Wikivoyage on 1 October 2026 · Something wrong or missing? Improve it on Wikivoyage
Best things about Pleasantville
Marmaduke Forster House
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 Nat…
Jacob Burns Film Center
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 Uni…
St John's Episcopal Church
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 si…
Rockefeller State Park Preserve
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 …
Graham Hills Park
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 r…
Opperman's Pond Park
Large pond with a small trail that goes around the lake. During the summer, fishing is allowed (catch-and-release), and during the winter, ice-skating is allowed (weather-permitting). The lake offers free parking spaces …
Plan your trip
Best time to visit & weather
Most comfortable: May–Oct. Summer highs reach about 84°F; winter lows dip to about 22°F. Cold months (Jan, Feb) can bring snow and ice; check road conditions. Wettest: Oct and Jun.
Blue bars: average daily high and low (°F). Purple columns: average monthly rain and melted snow (inches).
Getting there
- From you: to see whether to drive or fly, and how long it takes.
- HPN Westchester County Airport, White Plains — 6 mi away. Directions
- TEB Teterboro Airport, Teterboro — 24 mi away. Directions
- LGA LaGuardia Airport, New York — 25 mi away (major hub). Directions
Budget & where to stay
- Typical meal: about $20 per person at listed restaurants.
See the Sleep guide ↓ for places to stay.
Sample 3-day itinerary
Day 1
- Morning Jacob Burns Film Center, Pleasantville Farmers Market, Marmaduke Forster House
- Lunch Frank & Joe's Deli
- Afternoon Westchester Table Tennis Center, St John's Episcopal Church
- Dinner Crawdaddy's Creole Kitchen
- Evening Lucy's
Day 2
- Morning Rockefeller State Park Preserve, North County Trailway
- Lunch Dai Sushi
- Afternoon Graham Hills Park
- Dinner On's Chinese Kitchen
- Evening Foley's Club Lounge
Day 3
- Morning Nannahagan Park
- Lunch Tesoro D'Italia
- Afternoon Usonia Historic District
- Dinner Wood & Fire
Stops are grouped by area so each day needs little backtracking. Check opening hours before you go.
Food for you
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.
Cuisine (tap to filter)
What to ask about, for your diet
Diet labels come from each listing's description and cuisine; “likely” means the cuisine usually has good choices, not a promise. Check with the restaurant. Open the food finder
Photos
Map
Every listing with a location. Tap a pin for its Google Maps link.
Understand
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.
Climate
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.
Get in
By plane
- Westchester County Airport(HPN), 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) 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), John F. Kennedy International Airport (JFK), and LaGuardia International Airport (LGA) 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.
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
- Pleasantville station is an express stop on the Metro-North's Harlem Line in the center of the village. Express service between Pleasantville station and Grand Central Terminal is about 50 minutes. A one-way ticket from Grand Central also costs $11.25 off-peak and $14.75 peak. Local service is available between other Metro-North commuter stations. On-board train fares are subject to a stiff surcharge, so buy your tickets from the vending machines at the station or online on the MTA TrainTime app. Full weekday and weekend Harlem Line schedules are available online.
Get around
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.
See
See Jacob Burns Film Center
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.
See Marmaduke Forster House
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.
Do
Parks and preserves
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.
Do Rockefeller State Park Preserve
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.
Do Graham Hills Park
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.
Do Opperman's Pond Park
Large pond with a small trail that goes around the lake. During the summer, fishing is allowed (catch-and-release), and during the winter, ice-skating is allowed (weather-permitting). The lake offers free parking spaces on the side of the road.
Do Nannahagan Park
A multipurpose park centered around a pond with a walking trail. Offers playground equipment, a basketball court, a field, and the pond allows catch-and-release fishing. The pool on premises is only for town residents that have a membership.
Physical activities
Do North County Trailway
Built along the railbed of the former Putnam Division of the New York Central Railroad, the trailway provided rail service in the late 19th century and early 20th century from the Bronx to Putnam County. Nowadays, it is a 22.1 mi (35.6 km) paved, multi-use path that spans from Eastview to the Putnam County border, and provides access to many of Westchester's parks, preserves, and village downtowns. In some sections of the trail, the railbed is still visible. Free parking at the Pleasantville entrance.
Other
Do Usonia Historic District
The street is home to a planned neighborhood by famed architect Frank Lloyd Wright, who designed three out of the 47 houses in the neighborhood, the remainder being designed by many of his students in the Usonia style. The neighborhood is on the National Register of Historic Places, and while all of the houses are privately owned, many visitors do driving tours of the neighborhood, taking time to admire the unique architecture style that is rarely seem anywhere else in the country.
Buy
Downtown Pleasantville is home to nearly all small businesses and local independent restaurants. Street parking around all of downtown is metered, and the only parking that is free is around a quarter mile northeast of town. For the local supermarket, gas, and convenience items, head a quarter mile west of downtown on Bedford Rd. The gas is usually on the cheaper side when compared to other towns and villages bordering Pleasantville, and some of the gas stations are also full-service.
Shop The Village Bookstore
Quaint neighborhood book store selling a variety of genres of books, including autographed and rare copies, in addition to having author visits and book clubs. The store is frequented by President Bill Clinton, who can often be seen skimming books on the shelves. Paid parking is available in front of the store and around the back.
Eat
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.
Budget
Eat On's Chinese Kitchen
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.
Eat Lucio's Pizzeria
Popular pizzeria that sells pies, slices, pastas, and salads. Staff are no frills, but there is a nice atmosphere and the service is fast. Plenty of indoor seating available for eating in. The extra-large pie is not displayed on their menu in the store, but is a nominal upcharge from the large pie and is highly recommended. Delivery available. All parking around is metered.
Eat Sundance Deli
Deli serving up a variety of different breakfast plates and many wedges, paninis, and wraps. A local favorite with high school students in the surrounding towns, and usually busy during peak lunch time. Street parking in the area is all metered.
Eat Frank & Joe's Deli
Affordable Italian deli with a large grocery section, and large hot and cold Italian sandwiches. Their homemade chicken noodle soup is very popular, and the small store can get busy during the lunch rush. Street parking around the storefront is all metered.
Mid-range
Eat Wood & Fire
Neapolitan-style pizzeria with a great selection of pizzas by the pie, pastas, and appetizers. On the weekends, the restaurant gets very busy, so it is recommended to book a reservation in advance.
Eat Dai Sushi
Two-story Japanese restaurant that looks like it was built into a small house. Gets busy for dinner on the weekends, reservation recommended. Takeout is very popular, since there is no free parking near the restaurant. Offers many specialty rolls and a large sushi menu.
Eat Pubstreet
American restaurant built into the historic Pleasantville train station serving up delicious sandwiches, pub food, and oysters. In the summer, the restaurant offers outdoor seating, and the they have specials nearly every day of the week. There is metered street parking right in front of the restaurant.
Eat Crawdaddy's Creole Kitchen
New Orleans style restaurant in downtown Pleasantville with a dive bar and a lounge, serving up po' boys, fry baskets, and gumbos. Won an editor's pick in the Best of Westchester Awards in 2024. There is metered parking in front of the restaurant.
Splurge
Eat Southern Table
Southern-style restaurant serving up fried chicken, sandwiches, and barbecue. Voted by the Westchester Magazine for having the best southern food, and holds a Michelin Bib Gourmand. The restaurant can get quite busy during weekends and it is recommended to have a reservation. There is a free parking lot around the back of the restaurant.
Eat Tesoro D'Italia
Traditional Italian restaurant with a classy atmosphere and exceptional service. Offers a fully stocked bar and a large wine cellar. Free parking in front of the restaurant.
Drink
There are additional bars in the county seat, White Plains, a 15 minute car or train ride south.
Drink Foley's Club Lounge
Small laid-back locals' bar with the standard fare of drinks. Has a large bar food menu that is reasonably priced and large.
Drink Lucy's
Retro themed establishment with live music every weekend and a full bar. Always busy on Friday nights and weekends, and an affordable food menu.
Sleep
The closest hotels are in Tarrytown (15 minutes southwest by car) and White Plains (15 minutes south by car or train)
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.
Nearby
Chappaqua
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Briarcliff Manor
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