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8 Walks for All Seasons in Westchester County

Our Favorite Paths to Wander - Stroller Friendly Included

By Kelly Fitzpatrick January 28, 2025

Westchester County is home to countless scenic walking trails, and many of them are perfect for families with young children. Whether you're looking for a stroller-friendly paved path, a well-marked nature trail, or an easy walk with beautiful views, there’s a spot for you. These eight family-friendly walks offer a mix of Hudson River waterfront strolls, wooded escapes, and peaceful parks, all great for little legs (and wheels!). So, grab your stroller, lace up your sneakers, and explore some of the best kid-friendly walks in Westchester!


Tarrytown Lakes Estates

📍 Neperan Rd, Tarrytown

❤️ Really scenic, water views and woods. Extension trail is paved and stroller friendly.


Croton Landing

📍 1 Elliott Way, Croton-on-Hudson

❤️ While there are miles of waterfront walks in Westchester, this one is truly special. Stroller friendly.


Louis Engel Park

📍 25 Westerly Rd, Ossining

❤️ Riverside park with playgrounds and a splash pad in the summer + seasonal entertainment, restaurants, and more. Stroller friendly.


Lasdon Park

📍 2610 Amawalk Rd, Katonah

❤️ This Westchester County gem offers beautiful garden walks and a Veterans Memorial path. Many paths are sroller friendly, but can be easier with the carrier.


Mattiessen Park

📍 Bridge St, Irvington

❤️ A peaceful riverside park with gorgeous sunsets and a playground. Stroller friendly.


Westmoreland Sanctuary

📍 260 Chestnut Ridge Rd, Mount Kisco

❤️ Explore miles of trails through woods, wetlands, and open meadows + caregiver and me Fridays with animal visits. Use a carrier.


Gedney Park

📍 155 Millwood Rd, Chappaqua

❤️ A local favorite with wooded trails and a fun playground for kids + legendary sledding. Stroller friendly paths, but the trails are not suited for strollers.


Teatown Lake Reservation

📍 1600 Spring Valley Rd, Ossining

❤️ Scenic trails, a nature center, and a lake perfect for spotting wildlife. Bring the carrier.


What would you add to the list? There are so many great walks in Westchester!