Few town names are more optimistic than Pleasantville. What makes a place pleasant, after all? Is it the people who live there, or the businesses that line the streets, or simply something in the air? Whatever it is, the name gives the town a lot to live up to. But when you visit this Westchester village about 30 miles north of New York City, you find a place that feels, well, downright pleasant. With a walkable downtown, a first-rate independent film theater, and the biggest farmers market in the county all mere steps from Metro North, Pleasantville makes for an excellent day trip destination no matter the season. 

A LITTLE BIT OF HISTORY 

Pleasantville sits upon land once inhabited by the Wappinger, a loose confederation of Algonquian Munsee-speaking peoples. In the early 1800s, the village became known as Clark’s Corners, so named for Henry Clark, a local man who owned property at the corners of Broadway and Bedford Road. But in the 1820s, the new postmaster of New York, Henry Romer, was tasked by the federal government to come up with a proper town name for a planned post office; his first choice, Clarksville, was already taken, so he went with Pleasantville. During that time, the village was also a stop along the Underground Railroad’s path through the Hudson Valley, with fugitive slaves taking overnight refuge in a home owned by local Quaker farmer Joseph Pierce and his son, Moses, along with Moses’ wife, Esther. 

The arrival of the New York Central and New York and Harlem railroads (the latter of which would become the Metro-North’s Harlem line) in 1846 heavily spurred Pleasantville’s development by significantly cutting down travel time to and from New York City, resulting in its downtown shifting to be near the newly built train station and an influx of both industry and people. Small factories began to appear in the back half of the 19th century, and agricultural areas were redeveloped into housing for the growing population. Pleasantville itself was officially incorporated in 1897. 

Over the following years, the town became a commuter suburb thanks to the Harlem line. It also gained fame for its literary residents, like Lillian Hellman, who owned and lived on a farm on the town’s outskirts in the 1940s and 50s along with Dashiell Hammett. And it was the first headquarters of Reader’s Digest, which was founded by locals DeWitt and Lila Bell Wallace in 1922 and operated out of an office downtown until moving to Chappaqua in 1939.

Today, Pleasantville is an energetic, sought-after suburban enclave, with a population of just 7,500 occupying less than two square miles. But there’s more to this place than commuters packing onto Metro-North on their way to the big city. Here are some of our top picks to check out while visiting.

CATCH A FLICK AT THE JACOB C. BURNS FILM CENTER

The Jacob C. Burns Film Center is credited with revitalizing Pleasantville’s downtown, and it did so by using a piece of its past. In 1925, local businessman Granville Rome opened the first movie theater in Westchester County about a block from the Pleasantville train station: the Rome Theater, a single-screen movie palace of the kind that was popular in New York City and nationwide at the time. It stayed in business for the next 60 years, but the expansion of multiplexes and the deteriorating condition of the building forced its closure in 1987, and it remained vacant for the next decade. In 1998, a nonprofit group bought the theater with the intent of renovating it as both a site for independent films and as an arts center. It reopened its doors in 2001, still bearing the Spanish Mission-style design of the Rome and the name of a local lawyer whose family had contributed a large sum to its restoration.

Today, you can watch a movie at the Burns on one of its five screens, or you can check out the recently opened wine bar/cafe and gallery space (featuring special film-themed art exhibitions) on its second floor. The Burns shows newly released independent and foreign films and documentaries as well as awards contenders and classics, plus family-friendly movies, Q&A sessions with directors, actors and writers, themed screenings, live performances, and more. In addition, the Center runs a Media Arts Lab where local students can learn more about filmmaking; the building, just down the street from the theater, features classrooms, editing suites, animation and recording studios, and a soundstage.

It’s a fantastic theater dedicated to the art of filmmaking, and one well worth your time if you’re in town. 

FRESH PRODUCE, FISH AND MORE AT THE PLEASANTVILLE FARMERS MARKET 

The biggest year-round farmers market in Westchester can be found just steps from Pleasantville’s Metro North station. Every Saturday from 8:30 am to 1 pm, the Pleasantville Farmers Market hosts dozens of vendors offering the best homegrown and local produce, meat, seafood, dairy, and bread, plus specialties like fresh pasta, wine and spirits, every kind of pickle you could imagine, and even Tibetan dumplings.

Run by Foodchester, a volunteer non-profit, the Pleasantville Farmers Market is one of the most popular in the county, voted best in Westchester by the readers of Westchester Magazine every year from 2014 through 2023. As many as 60 different vendors set up shop in Memorial Plaza, rain or shine, even in the depths of winter. When you enter, you can consult a giant map with the market layout telling you who’s offering their wares, with a regular cast of weekly vendors joined by a rotating group of specialty sellers. The market also features live local music, ranging from jazz to bluegrass to folk, and a small space for kids and families to sit, spread out and enjoy the vibes.

You can find just about any foodstuff at the market, too. Looking for handmade cheeses? Chaseholm Farm Creamery from Pine Plains offers soft, spreadable cheeses, both pasteurized and raw, or you can sample Edgwick Farm’s selection of goat cheeses. Find the perfect crusty loaf for that cheese at Bien Cuit, which makes the trek up from Brooklyn to offer freshly baked breads and pastries, then snag a jam or jelly for your leftover slices at Wright’s Farm, hailing from Gardiner. Greens and salad mixes are the specialty at Poughquag’s Maple View Farms stand; fungi of all kinds are the star at Tivoli Mushrooms. Pura Vida Fisheries from Hampton Bays is the choice for seafood, and Hilly Acres Farm from Jeffersonville and Woven Stars Farm from Ghent are the places to go for meat and eggs, though if it’s duck you’re seeking, you’ll want to stop at Hudson Valley Duck Farm, which raises its fowls cage-free in Ferndale. Need some fruit or vegetables? Mead Orchards of Tivoli and Gajeski Produce from Riverhead have you covered. 

There’s plenty of prepared food, too. Knot of This World brings gigantic chewy soft pretzels from Levittown; Himalayan Delish, found in East Elmhurst, turns out momo, or Tibetan dumplings, both fresh and frozen. Fresh pasta is the focus at Trotta Foods from Thornwood, which sells sauces, too. The pastries at Strudel House from Hudson are sweet and savory; so are the pies at Noble Pies, a family-owned bakery in Warwick. Your kids will go nuts for the popsicles at Puras Paletas from West Orange, New Jersey or the cookies at Red Barn Bakery from Irvington. If you’re feeling adventurous, stop at Pickle Licious from Teaneck, New Jersey, to get their pickle on a stick. 

Beyond food, you can also pick up handmade soap at Sallyeander from Beacon, local honey from Verplanck’s Hudson River Apiaries, wine from Warwick Valley Winery & Distillery or Whitecliff Vineyard in Gardiner, vodka and other seasonal batch alcohols made with local ingredients (like ramps!) from Cooper’s Daughters Spirits of Hudson, and locally brewed teas and coffees at Teagevity of Nyack. And all of this is just a taste of what the Pleasantville Farmers Market has to offer. Bring lots of reusable bags and a big appetite. 

PICK UP A PADDLE AT THE WESTCHESTER TABLE TENNIS CENTER 

A five-minute walk from the train station, you’ll find the Westchester Table Tennis Center, where you’ll be greeted with the soft, metronomic sound of ping pong balls clacking from paddle to table to paddle to table. Featuring 30 tables and open seven days a week, it's where you’ll find some of the best table tennis players in the area, if not the country, practicing their craft or taking part in monthly tournaments. But fear not, the WTTC is open to players of all skill levels, from pros to novices. For those looking to become ping pong masters, three former pros — including Rawle Alleyne, the former coach of the Barbadian national team, and Kokou Fanny, seven-time table tennis champion of Togo — offer private lessons. If all you want is a table and some space to trade shots with a friend or your kids, you can buy a day pass or sign up for a membership. There are also after-school programs and league competitions two nights a week. 

MORE EXPLORING 

The annual Pleasantville Music Festival, known as New York’s Backyard Jam, has taken place every July for the last two decades, bringing together nationally known performers and smaller local bands for a full day of rock, blues, reggae, jazz, and more. The festival, which is held at Parkway Field, an eight-minute walk from the train station, will feature three stages — the Main Stage, for the biggest acts; the Chill Tent Stage, for more mellow acoustic performances; and the Party Stage, for more up-tempo pop acts — as well as a beer garden, food court, and vendor village. There’s also a space for kids (who can attend for free) featuring face-painting and games. This year’s festival starts at noon on Saturday, July 13, rain or shine.

Bibliophiles should be sure to check out The Village Bookstore, an independent family-owned seller that’s been in business since 1972. With over 10,000 books in stock as well as greeting cards, notebooks and gifts, they’re sure to have something for you — plus they host local author readings and book launches, as well as reading parties for kids. 

Pleasantville’s downtown area is small, but it doesn’t lack for good restaurants. Among the top choices in the area: Pubstreet, a brunch-and-dinner joint located in the town’s former train station, offers a raw bar and happy hour specials; Southern Table Kitchen & Bar serves fried chicken and other treats from below the Mason-Dixon line; Wood & Fire dishes out Neapolitan pizza; and Fatt Root is a noodle bar that also has dumplings, buns and Asian-inspired cocktails. For those looking for a quick bite, check out The Taco Project; their fish taco is crispy and fresh, topped with a bright and spicy salsa. Or head to Falafel Taco, which offers a mashup of middle eastern and Mexican flavors. And if you’re thirsty, stop in at Soul Brewing Company, which brews its beer on location to serve in its spacious taproom. 

For hardcore foodies, Pleasantville is a 10-minute rideshare away from Blue Hill at Stone Barns, the Michelin-starred restaurant famous for its farm-to-table fare and ethos. Reservations are required but hard to come by. 

If you can’t score a table at Blue Hill, you can satisfy your inner chef by taking a class at the Zwilling Cooking Studio, which offers group lessons in preparing all kinds of cuisines as well as knife skills classes and a kids summer camp. Afterward, you can stock your kitchen from the Zwilling Shop. The company is famous for its knives, all of which can be found on display in their Pleasantville store along with blenders, pots and pans, and much more. 

There’s plenty of nature to enjoy around Pleasantville. Those looking for a pleasant stroll through the trees should head to the Rockefeller State Park Preserve, a five-to-10-minute carshare from the train station just off NY-117 and comprised of over 1,700 acres of land that used to be part of the country estates of the Rockefeller family. (Blue Hill at Stone Barns is also located on the property.) The trails are former carriage roads, 45 miles in all, that are ideal for walking, jogging, or horse riding. Inside the park you’ll find a peony garden with flowers donated from Japan; the 22-acre Swan Lake; a small historical museum; the remains of Rockwood Hall, the Gilded Age mansion of William Rockefeller; and opportunities to birdwatch, fish and hunt. Dogs are also welcome, provided they’re on a leash. 

If you’re looking for a little more adventure, then Graham Hills Park, also off NY-117 and about one mile from the train station, will be more your speed. The 431-acre park has five miles of trails for hikers and mountain bikers, as well as a small skills and terrain park with jumps and ramps for the X-Games aficionados. And for a longer bike ride, Pleasantville is the closest stop for the North-South County Trailways, which cover roughly 36 miles in Westchester and run along the old Putnam Railroad of the former New York Central Railroad line. The trail is about a mile’s ride from the train station, with access near Graham Hills Park. Here’s everything you need to know about bringing your bike on Metro North.

GETTING THERE

Easily accessible by Metro North, Pleasantville is just 50 minutes from Grand Central on the Harlem line, with multiple trains leaving every hour. The Pleasantville station is centrally located, just a few hundred feet from both the plaza where the weekly farmers market is held and the Jacob C. Burns Film Center, as well as the popular downtown stretch of Wheeler Avenue between Bedford Road and Manville Road/NY-117. 

While at the station, check out the 22 cast bronze sculptural chairs, these artworks, titled "Almost Home," were created by Kane Do and Jane Greengold.