Spotlight on Westchester: Ossining


We all love our own little cozy corners of Westchester. There are so many things to do and see, places to eat, parks to visit. We love exploring the county and “finding” the kid-friendly gems! Even if you have lived here your entire life, you can still find new fun things to do all the time. It is our mom-bloggin’ duty to highlight some of those awesome places so that other moms can take advantage too! With each installment one or two new towns/cities will be highlighted to give you a glimpse into the awesomeness that is Westchester! Be sure to 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: Our library is big, beautiful, and offers a metric ton of fun activities for kids. From the children’s library to the weekly playgroup classes, OPL is a lovely spot to spend a rainy afternoon or to learn alongside your little ones. There is also a great performance space downstairs that frequently hosts concerts, art shows, and other community events. Check out their calendar to see what’s coming up.

Dragonfly Wellness: The best yoga instructors around. Dragonfly has a beautiful and unassuming space, perfect for a quick retreat from the every day. Check out a class and you’ll feel refreshed and serene as you head back into the world.

Mike Risko Music: A full service music store and music school, Mike Risko Music is a great community spot. If you’re looking for music lessons for yourself or your child, this is the place to go. Some of their unique programs include adult rock band (they have it for kids too) and children’s theater productions. If you’re looking for live music, The Mike Risko Band is great, and they perform all over Westchester. They often host free shows of their students performing and do kids’ birthday parties too.


Head Outside:

Louis Engel Park: This riverfront park adjacent to the train station is the home of many wonderful O-Town festivals and events. Friday nights in the summer feature a fabulous concert series, and in April the park hosts the biggest Earth Day celebration in Westchester. It’s also a great place to just throw rocks in the river with kids. When the weather warms up, Engel Park’s spray park is a super fun place to splash around.  

Veteran’s Memorial Park: This park has something fun going on at all times of the year. In the winter you can pack up your skates and hit the ice at Vet’s park. They have a playground, fields, and small picnic pavilion as well. Ossining has a great park in nearly every neighborhood.  Check out the map here for more info. 

Ossining Farmers Market: Venture down Main to Market Square on a Saturday morning and you’ll find a wide variety of seasonal produce along with free range meat and eggs, bread, and pickles. The farmers market is year-round, but moves indoors during the coldest months.

Teatown: My favorite place to hike and picnic, Teatown boasts an amazing nature center and beautiful scenery. You can walk around the lake and unpack your lunch at the gazebo or meander around the birds of prey trail. Go during the week when parking is free.  

Where to Eat:

DD’s Diner: Our go-to place for after church, DD’s is one of the areas newer diners and serves up a menu of delicious sandwiches, salads, and breakfasts.  

Good Choice Kitchen: This place makes vegan food that even the most serious carnivores can enjoy. I highly recommend the chickpea scoop and the kale salad. Best of all, they have a healthy and delicious kids’ menu and are very family friendly.

3 Westerly: Good for date night, 3 Westerly sits alongside the Hudson River and has a killer view and vibe.  

Cravin’ Jamaican: Two words people – jerk. chicken. The portions here are huge, and the prices are excellent. This is a great option for takeout on the way home from the train station.  

First Village Coffee: Visit First Village for some caffeine and a pastry. Your little ones can read one of the many children’s books on the shelf while you sip.  

Capri: I go for the Alfredo, but Capri also offers pizza and a full Italian menu. It’s super family friendly. One of my son’s most epic meltdowns happened at Capri. When we decided to leave early several members of the staff came over to tell me that no one minded that my kid was screaming his lungs out.  

Los Abuelos: Another great spot for family meals, Los Abuelos has amazing table side guacamole that my son devours.  

Ossining is a wonderful river town with fun for the whole family during any season. What’s your favorite place to visit in Ossining?

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Amy is a Hudson Valley native and educator working in New York City schools. She has two little kids and one little dog. Before moving to her current home in Ossining, Amy attended college on Long Island and then spent most of her 20s in Brooklyn and Queens. New York is truly home for her, and she’s thrilled to be living closer to her hometown of Garrison and her extended family. As a mom, Amy believes in empowered parenting, and she’s passionate about raising her kids to be partners in the fight for social justice. When she’s not working or trying to figure out nap time, Amy loves hiking, yoga, swimming, and relaxing with her family.