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.
While 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: 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: 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.
The Tiny Mess Club: Looking for more opportunities for toddler activities outside the library? The Tiny Mess Club offers classes and parties for young kids that lean into their love for messy sensory play. This newer addition to the village provides additional indoor activity options for the youngest kids.
Pleasantville Parks and Recreation Department: For Pleasantville village residents, there are ample opportunities for classes and fun for the entire family. The village hosts a perennially loved camp program, and there are additional recreation opportunities for residents of all ages. Don’t forget about the newly renovated pool complex, complete with a splash pad and a water slide!
Pleasantville Pride: Pleasantville is proud to host a yearly family-friendly Pride celebration, and also has an active queer alliance (prior meet-ups have included delicious baked goods and fun kids crafts, as well as supportive conversations for the teens and adults). Yearly pride celebrations usually include ice cream, food, live music, crafts, and a children’s story time. It is a lovely and warm celebration for the LGBTQIA2+ community that also attracts many, many ally families, and offers an opportunity to connect and celebrate community.
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).
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.
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
Fatt Root: I won’t lie. I do take out from Fatt Root too often. But how could I not, when their food is so delicious? I’m partial to their tuna poke bowl, but there is nothing bad on the menu. They offer a well-rounded list of Asian staples, from ramen to kimchi and Korean BBQ entrees, and there are plenty of vegetarian options, too. They also have a large cocktail menu, including mocktails for those who enjoy an alcohol-free lifestyle.
Pubstreet: No Westchester community is complete without the train station restaurant, and Pubstreet is by far my favorite of the ones I’ve visited. Seafood and pub fare blend seamlessly in this trendy spot, and the food is delicious.
Black Cow Coffee Company: When you think of the best coffee shops, what do you think of? Great coffee? Community? Art? Events? Wifi? Black Cow has all of this and more. The neighborhood staple is a hub of activity all day, and whether you are grabbing coffee with a friend or looking for a nice public spot to work for a bit, Black Cow fits the bill!
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.
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).
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.
