Family-Friendly Outdoor Winter Activities in the Westchester River Towns
We’re all looking for ways to get out of the house in the Westchester River Towns during the winter months. Fresh air does wonders for everyone’s mood — and it’s a great way to help kids burn off some of that extra energy, even when it’s cold outside.
Whether you’re bundling up for snow play or taking advantage of those milder winter days, there are plenty of family-friendly outdoor winter activities near the River Towns to enjoy. Some are right in our riverfront villages, and others are just a short drive away.
Outdoor Winter Fun in and Near the Westchester River Towns
1. Hudson RiverWalk & Riverfront Parks
The Hudson RiverWalk winds through Dobbs Ferry, Irvington, Tarrytown, and Sleepy Hollow, offering beautiful winter views of the river. Kids love spotting boats, birds, and even the occasional train, while parents appreciate the flat, stroller-friendly paths.
Details: Open daily | Free | All ages
Link:
https://www.hudsonrivergreenwaywatertrail.org
2. Rockefeller State Park Preserve (Pleasantville)
Not far from Sleepy Hollow, Rockefeller Preserve is a winter favorite for hiking, snowshoeing, and peaceful nature walks. Trails are wide and manageable for kids, and winter brings especially beautiful views of fields, woods, and frozen ponds.
Details: Open daily | Free parking | All ages
Link:
https://parks.ny.gov/parks/rockefeller
3. Pierson Park & Scenic Hudson RiverWalk Park (Tarrytown)
These riverfront parks are great spots for winter walks, bike rides on milder days, and letting kids explore open space safely. Snowy days turn the river views into something extra special.
Details: Open daily | Free | All ages
Link:
https://www.tarrytownny.gov
4. Local Sledding Hills (Weather-Dependent)
When snow hits, Rivertown families head to favorite sledding spots like Dobbs Ferry Waterfront Park, Hillside Woods in Hastings, and nearby community fields. Even a small hill can provide big winter fun.
Details: Weather-dependent | Free | Best for ages 3+
Link: Check local town parks pages for conditions
5. Croton Gorge Park
Croton Gorge Park is a scenic spot to visit in all season, even in winter. Kids love seeing the massive dam, and snowy or icy conditions make it feel like a winter adventure (with appropriate footwear!).
Details: Open daily | Free | All ages
Link:
https://parks.westchestergov.com/croton-gorge-park
6. Winter Festivals & Outdoor Events
Winter in and around the Rivertowns comes with some truly special outdoor events that families look forward to each year. Maple tapping and sugaring programs at places like Rockefeller State Park Preserve and nearby nature centers let kids see how sap turns into syrup — a hands-on winter favorite. Another can’t-miss event is Teatown Lake Reservation’s EagleFest, where families can spot bald eagles along the Hudson River and enjoy outdoor walks, animal encounters, and nature activities. These events are seasonal, educational, and perfect for getting outside during the colder months.
Details: Dates vary (late winter) | Cost varies | All ages
Link:
https://www.teatown.org • https://parks.ny.gov/parks/rockefeller
7. Old Croton Aqueduct Trail
This historic trail runs right through several Rivertown communities and is perfect for winter walks, bike rides, and nature scavenger hunts. It’s a quieter, underrated option when you want something simple and flexible.
Details: Open daily | Free | All ages
Link:
https://parks.ny.gov/parks/oldcrotonaqueduct
Don’t Miss: More Winter Fun in the Westchester River Towns
Looking for even more things to do this winter?
👉 Be sure to check our Westchester River Towns events calendar for the latest family-friendly winter events, pop-ups, outdoor activities, and seasonal fun happening near you.
