We all love our own little cozy corners of Westchester. There are 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.
Ossining is a beautiful and vibrant Hudson Line community in Northern Westchester. With its lovely downtown and beautiful riverfront, Ossining is a wonderful place to live or visit. With or without the kiddos, there’s plenty to do.
What To Do
Ossining Public Library: The library remains a fantastic hub for learning and community. With tons of kids’ programming, storytimes, and workshops, plus exhibits and performances in the downstairs event space, it’s perfect for a rainy day or enriching afternoon. Check their calendar to see what’s coming up.
Mike Risko Music: A long-standing music school and community spot in Ossining, offering lessons, performance opportunities, and music retail. They frequently host student showcases and local performances, plus programs like adult rock bands and kids’ musical theater.
Head Outside
Louis Engel Waterfront Park: A favorite riverfront space adjacent to the train station for strolls, picnics, and community events. In the summer, it hosts music, food, and festivals, and kids love throwing rocks or splashing around when it’s warm out.
Henry Gourdine Park: This park along the Hudson features playgrounds, walking and biking paths, and often hosts community events such as jazz forums and River Jam concerts.
Ossining Farmers Market: The year-round Saturday market in Market Square (Main St.) offers seasonal produce, baked goods, homemade treats, and more. It’s a great family morning ritual.
Teatown Lake Reservation: Just a short drive away, Teatown offers trails, a nature center, lake viewpoints, and picnic spots. It’s perfect for hiking and exploring nature with kids.
Where to Eat
Classic & Local Favorites
DD’s Diner: A go-to for breakfast, lunch, or diner classics with generous portions and a welcoming vibe — great with kids or friends.
Cravin Jamaican Cuisine: Fantastic jerk chicken and Caribbean favorites with large portions and excellent prices. This is a popular takeout and dine-in option.
Los Abuelos Restaurant: Family-friendly Mexican with standout table-side guacamole and hearty flavors.
Aji Limo Peruvian Cuisine: Serving Peruvian favorites with vibrant flavors — a local touch of something different right on Main Street.
Melike: Turkish cuisine and Mediterranean flavors are a lovely addition to Ossining’s dining scene, with creative dishes.
Frytanga Cafe: A newer coffee spot with highly rated drinks and a cozy vibe, expanding convenient places to grab a cuppa downtown.
Waterfront & Date Night
3 Westerly Bar & Grill: Scenic riverside dining with views of the Hudson that is ideal for a date night or a sunset dinner.
The Boathouse: A casual waterfront spot for seafood, burgers, and drinks. It’s perfect for a relaxed meal by the river.
Brothers Fish & Chips: A local pick for seafood classics with creative twists that is great for lunch or a casual dinner.
Other Tasty Spots Around Town
Casa Latina Bar & Grill: Latin-inspired comfort food with excellent flavors and a friendly atmosphere.
Churrasqueira Ribatejo: Portuguese eats with grilled meats and seafood — a unique local taste.
Capri Pizza & Pasta: A family favorite serving comfort Italian classics like pizza, pasta, and more.
Hacienda Greek Restaurant: Delicious Greek cuisine for a sit-down dinner with rich flavors.
Tutto Cream: A must-visit with gelato, sorbet, coffee, cakes, and tarts.
