12 Things to Do in Ossining with Kids (or Without)

There are lots of things to do with kids in Ossining. Some of the activities on the list – like the visit to Teatown – could take as much as a few hours, and others as little as 20 minutes! Though we do love places nearby like Muscoot Farm and the New York Botanical Garden, this list is limited to some of my favorite activities and places to enjoy with kids within the Town of Ossining. Shhh don’t tell anyone, but most of these are great activities even without kids!

1. Visit our amazing library:

The 44,000 square foot library is definitely one of the highlights of our town. In addition to lots of book, it has a children’s zone, a teen zone, an art gallery and a theater. The library organizes concerts, film festivals and offers free classes for kids. Visit their website: https://www.ossininglibrary.org/ to see hours, programs and events. As a member, you can also access free passes to area museums, but you may need to wait as they have limited numbers available for each museum.

Pictured: The Kids Room at the Ossining Public Library

2. Have a picnic with a river view:

Take advantage of the beautiful views we have at the waterfront! Come to Louis Engel Park (see more about the park) with food and a picnic blanket for a delightful time with the family. On your way to the waterfront, you can stop by Main Street Deli Cafe on 143 Main Street or The Village Deli & Cafe Of Ossining on 97 Main St and grab a couple of sandwiches or prepared meals. Alternatively, there are grills around the playground and by the water in front of the spray park if you’d like to bring charcoal and cook on the grill.

The kids can play in the playground and bring bikes or scooters for a great ride along the park’s paved path.

3. Go to Teatown for a family hike:

Teatown is a 1000-acre nature preserve and education center located right here in Ossining. There are many different trails available, but the best one to do with kids is the trail that runs around the lake. Plan for an hour to make it all the way around the lake, although it could be shorter if you move fast and longer if you stop frequently to explore along the way. When you’re done with the hike, head to the main facility area to see rescued animals, visit the Nature Center and consider becoming a member. 

Pictured: The Bergmann Bordwalk at Teatown

4. Walk the Sing Sing Kill:

Park at the lower parking lot of the Joseph Caputo Community Center located at 95 Broadway and enter the Sing Sing Kill Greenway. Here you can see the Sing Sing Kill’s rocky gorge, pass under the Double Arch bridge and follow the path of the brook that flows under the walkway. The trees protect you from the sun in most spots and the steel railings keep the kids safe! Opened in April 2016, the Greenway is an approx. 2/3 of a mile round trip and wheelchair accessible when entered from the community center (for more info on the Greenway click here).

Pictured: My toddler at The Sing Sing Kill 

5. Go for a culinary trip: 

Ossining is a town with people from many nationalities, which is reflected in the multitude of food options your family can enjoy. Try some Jamaican at Cravin’ Jamaican Cuisine, Portuguese at Churrasqueira Ribatejo or Doca’s, Colombian at La Estacion Paisa, Mexican at los Abuelos, Peruvian at La Gladys III or Aji Limo, or mixed Latin American at Karma Lounge. We love to travel, so exposing our kids to new foods and flavors has always been important for us.

Pictured: Typical Portuguese food enjoyed at the Portuguese Festival (held every June on Main Street)

6. Bring the kids to the playground:

There are 13 playgrounds in Ossining (you can see the full list here), so no matter where you are, you can find a playground near you. My kids’ favorite playground is at Buck Johnson, but I love Louis Engel and Henry Gourdine because of the beautiful river views.

Pictured: Henry Gourdine Park and Playground

7. Take a dip in the pool:

The town pool is open for all town residents, you just need to go to the Community Center to get your rec card and your pool pass. Among other activities, they offer open swim hours and paid swim classes for all ages. Right next to the pool there is a little splash pad great for kids.

8. Walk the Aqueduct Trail:

Right off Main Street you can find an entrance to the trail that follows the Old Croton Aqueduct, which was built between 1837 and 1842 to supply water to New York City. This walk will take you over the Double Arch (you can see the Sing Sing Kill below), by the Ossining Heritage Area Visitor Center (in the Ossining Community Center building), and you can keep walking all the way to the Croton Dam if you’d like. You can access the trail next to Open Door on Main Street. To see more info on the trail, visit NY NJ Trail Conference.

9. Go for a bike ride:

There are many bike routes you can take in Ossining. The North County Trailway (map) and the Old Croton Aqueduct Trail (map) are both accessible from Ossining. The stretch of the North County Trail most easily accessible is over 22 miles long and largely paved. The Old Croton trail is 26 miles long and runs from the New Croton Dam all the way down to Yonkers and has sections of dirt, gravel and asphalt.

Our favorite bike route to do with kids is a section of The North County Trailway, accessed either at a parking lot in Yorktown on Route 118 (link to Google Maps location) or on Route 134 (link to Google Maps location). The first location is a bit further drive but has a parking lot, so it’s easier to unload there. The second location is right on Route 134 at a sharp curve in the road. There is space on the shoulder to park and lots of people do it, but you need to be very careful with the kids while unloading.

Pictured: The North County Trailway next to the access point at Route 134

10. Attend a fair or festival:

There are over a dozen festivals that happen every year in Ossining. You can bring the kids to collect eggs at the Eggstravaganza egg hunt, do yoga at the Ossining Annual Health and Wellness Fair, learn about how to take better care of the environment at the Earth Day Festival, enjoy Portuguese music and food at the Portuguese Festival, enjoy rides at the Saint Ann’s Festival or the Saint Augustine’s Italian Festival, enjoy the concert and fireworks at the Fireworks celebration, carve a pumpkin at the Fall Family Fun Day or have breakfast with Santa in December! For upcoming events in Ossining, check out our events page. You can also check out a list of Ossining’s annual celebrations and festivals by month here.

Pictured: Fun at the Saint Augustine’s Festival

11. Walk the Ossining Reservoir and look for fish, birds, and turtles:

The reservoir was the Village’s water supply for much of the pre-World War II era, and then was replaced by water towers. Now the reservoir, part of the Richard Wishnie Park, has an asphalt ring around it for walking. Complete 3 laps to walk a mile! It isn’t meant to be a true bike path, but kids could use scooters or bikes, being aware that the path is primarily for walkers. There are park benches to take a rest, and if you get lucky looking in the water you might spot fish or turtles.

The reservoir on a winter day (its nicer in the summer!)

12. Visit the Farmers Market:

A visit to the farmer’s market is one of our favorite things to do on the weekends. Located at the parking lot at the corner of Spring St & Main St (from May to December), it runs from 8:30 AM until 1:00 PM. I want my kids to grow up appreciating real food and the people that grow it, and the farmer’s market is a great place to support that. The kids get to talk to farmers and producers of other food, pick their favorite fruits and vegetables and sometimes even enjoy special activities and live music. Before we leave we always grab a little treat from one of the vendors that offer baked goods.

And that’s it! That wraps up our list of 12 things to do in Ossining with kids. There are many more activities you can do with your kids in town, and I would love to hear your favorites.

We are always looking for new adventures close to home.