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Village in New York, United States
Photo: Simon Geisker, CC BY 3.0 via Wikimedia Commons
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.
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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.
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.
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.
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.
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.
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.
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.
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.
21,000 square foot table tennis facility with over 30 tables. Day pass includes paddles and ping pong balls. Offers monthly USATT-rated 4-star tournaments.
Private nine-hole golf course five minutes from downtown Pleasantville. Has a pool, tennis and pickleball courts, and a driving range. Designed in 1926 by A.W. Tillinghast. 2121 yards, par 32.
Largest year-round farmers market in Westchester, offering local produce, freshly baked bread, and more. Voted the Best in Westchester by the Westchester Magazine for 11 years in a row. Not all vendors accept credit cards, so bring cash.
The studio for the knife company offers instructional classes on cooking world cuisine, sharpening knives, and mastering basic cooking skills, and is family-friendly, and beginner friendly.
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.
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.
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.
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.
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.
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.
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.
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.
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.
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.
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.
Small laid-back locals' bar with the standard fare of drinks. Has a large bar food menu that is reasonably priced and large.
Retro themed establishment with live music every weekend and a full bar. Always busy on Friday nights and weekends, and an affordable food menu.
Locally owned and operated winery producing four types of wine using California Gold Coast grapes, in addition to selling raw grapes and winemaking equipment. The winery allows customers to "fill their own container" for a 20% discount.
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.
Gallery gift shop that offers a variety of unique gifts ranging from clocks, scarves, jewelry, and garden items. All of the items are produced by American artists and designers and are handpicked for sale by the owner. Rated Best in Westchester for two years.
Small but overflowing shop with an incredible variety of homemade chocolates and other sweets. Custom pieces can be made, and all the chocolate sold is homemade.
Small boutique clothing shop offering unique clothing described as "independent fashion with a floral twist." Clothing is usually discounted and at a reasonable price.
Downtown Pleasantville is not very large, and with free parking in downtown being nonexistent, you are better off walking.
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