Spotlight on Westchester :: Pleasantville


We all love our own little cozy corners of Westchester. There are so many things to do and see, places to eat, and parks to visit. Who doesn’t love exploring the county and “finding” the kid-friendly gems! We are spotlighting some of those awesome places so that other moms can take advantage and get a glimpse into the awesomeness that is Westchester! Read all posts in our Spotlight on Westchester Series.

PleasantvilleWhile many other publications sing the praises of surrounding communities, Pleasantville is often considered a hidden gem, flying under the radar and less popular at the top of lists for great places to raise your family in Westchester.

I can’t see why! The schools are fantastic, the community is warm and welcoming, the village is small and walkable, and homes are more affordable than the surrounding areas. The village has an artsy, cool, and a bit of an industrial vibe while somehow meeting the definition of a quaint small village at the same time! Check pretentiousness at the village border. Pleasantville is down to earth and more economically diverse than many other nearby communities. It is also more diverse in general! Here are just a few reasons to love Pleasantville, NY.

What to Do

Pleasantville Farmers Market Photo Credit: Erin Kirby

Pleasantville Farmers’ Market: Held each Saturday (all year, with the market moving indoors during cold months!), the Pleasantville Farmers’ Market is among the best around. With food stalls (think waffles, samosas, and Jamaican-style cuisine), live music, kids’ activities, and dozens of vendors selling everything from produce to meats, spices to flowers, and more, the market is sure to be a stop the entire family will love.

Mt. Pleasant Library (Pleasantville): The Pleasantville Library is a great community resource. Aside from offering the standard children’s room, study rooms, museum passes, books, etc., the library also has a variety of great programming for everyone in the family. We especially love the story times offered on Mondays, Wednesdays, and Fridays with Ms. Debbie.

Jacob Burns Film Center: Located just steps from the MetroNorth station, the Jacob Burns Film Center has multiple theaters and offers a wide variety of film-related programming for kids and adults. Despite being located in such a small community, it has been an official Sundance Film Festival partner!

Pleasantville Music Festival: You read that right! The tiny village of Pleasantville has its own [quite popular] music festival! Held each summer, it sells out quickly, so be sure to get your tickets early.

The Village Bookstore: Who doesn’t love supporting independent bookstores? This is a great stop for any book lover; it has a great selection, and the staff is knowledgeable and passionate about literature.

Head Outside

Playgrounds: Pleasantville has several wonderful playgrounds, including Roselle (which is found on many best playground lists), Nannyhagen, and Soldiers and Sailors. Nannyhagen is also home to the village pool and a lovely walking path around a stream and small pond (popular with fishermen and open for skating in the winter when cold enough).

 Nannyhagen Pond and Playground (seen in the background) Photo credit: Erin Kirby
Nannyhagen Pond Photo credit: Erin Kirby

Take in Nature: Rockefeller State Park Preserve is 1771 acres of woodland, marshland, fields, ponds, and streams situated on the east side of Pleasantville (just outside of the village proper, though some are also in surrounding communities such as Sleepy Hollow). 45 miles of carriage trails are easy to navigate with a stroller or young children. The park is also adjacent to Stone Barns, which offers additional walking trails. It is by far one of my family’s favorite places to go for a hike together.

Swan Lake at Rockefeller State Park Preserve in the summer Photo credit: Erin Kirby
Rockefeller State Park Preserve in the fall Photo credit: Erin Kirby

Learn about Agriculture, Sustainable Farming, and Farm to Table Dining: Stone Barns Center for Food & Agriculture is technically not in Pleasantville (it is instead in adjacent Pocantico Hills), but it is close enough to make it a huge part of the local community. Stone Barns offers a variety of programming on their 80-acre property and is home to the perennially award-winning Blue Hill at Stone Barns. The restaurant currently holds two Michelin Stars and ranks among the best restaurants, not just in the area but in the world.

Where to Eat

Southern Table: One of the first Michelin guide entries from Westchester County, Southern Table is a trendy stop popular with celebrities and locals. The menu offers a mix of southern comfort food staples and southwestern fare and is open for brunch on weekends, too.

Wood and Fire: A great stop for Neapolitan-style pizza, it is ranked as one of the best pizza places in the county and has very much earned that title. Frankly, the pizza is better than a lot of the pizza we had when we lived in NYC.

Lefteris Gyro IV: Lefteris Gyro is a Westchester staple, with locations across the county. Serving up delicious, unpretentious Greek classics, Lefteris has been a welcome stop for my family (who moved from Astoria, Queens, home to a large Greek population and many amazing Greek restaurants).

Jean Jacques: Jean Jacques offers catering, breakfast, sandwiches, and baked goods, but they are our favorite place in the area for cappuccino and croissants!

Second Mouse Cheese Shop: Fresh cheese, cured meats, and sandwiches made while you wait (plus pretty much anything else you need for your cheese board). Second Mouse is a favorite stop for grabbing cheese plate items for parties, an elevated everyday snack, or a quick lunch.

Craft Pizza and Beer: Great pizza, including tons of options for those with unique dietary needs (including plenty of gluten-free menu items). Craft also offers standard pub fare. With its great outdoor patio, it is a popular stop for outdoor dining during the nicer months.

Root2Rise: Vegan and gluten-free food that is worth it, even for people who aren’t vegan or gluten-free. Believe it! Root2Rise is one of my favorite spots to grab lunch. Healthy and delicious, it is a not-so-guilty pleasure.

Where is your favorite spot in Pleasantville?

To read all posts in our Spotlight on Westchester series, click here.

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Erin is the mother of one sweet, rambunctious toddler and wife to a talented chef. Professionally, she is a former special educator and preschool teacher, and is currently a cognitive neuroscience researcher and Ph.D candidate in Cognitive Science in Education with specializations in neuroscience, cognitive development, and neurodiversity/autism. She holds masters degrees in cognitive science, and neuroscience in education, from Teachers College, Columbia University, and undergraduate degrees in special education (with an additional concentration in elementary education and a minor in English) and early childhood education. As the wife of a chef, food is a huge part of her family culture, and she enjoy both cooking and baking. Some of her other hobbies include hiking, traveling, jogging, meditation, animal rescue, playing piano and guitar, crafting, reading, and of course, writing. You can follow her parenting journey and pick up tips on great kids activities here on Westchester Moms Blog, as well as her website (, Facebook, Instagram, and Pinterest accounts.