Macaroni KID Guide to Sledding Fun

Sledding Hills for Little and Big Kids in Armonk, Chappaqua, Mount Kisco, Pleasantville and Beyond

By Kelly Fitzpatrick January 6, 2024

Get ready for some snow fun and sledding with Macaroni KID Armonk, Chappaqua, Mount Kisco, Pleasantville’s guide to sledding in our area of Northern Westchester.  There are lots of great places to sled in Westchester County and our Northern Westchester neighborhoods have some of the best spots for little kids and big kids alike!  Whether you tube, saucer, or toboggan these hills are sure to help you find your family fun during a day out in winter weather!

And family time is most fun when it’s safe!  Check out these tips from Maria Fareri Children’s Hospital on sledding precautions:

  • Keep sledders away from motor vehicles.
  • Children should be supervised while sledding.
  • Keep young children separated from older children.
  • Sledding feet first or sitting up, instead of lying down head-first, may prevent head injuries.
  • Consider having your child wear a helmet while sledding.
  • Use steerable sleds, not snow disks or inner tubes. Avoid sledding in crowded areas.
  • Sleds should be structurally sound and free of sharp edges and splinters, and the steering mechanism should be well lubricated.
  • Sled slopes should be free of obstructions like trees or fences, be covered in snow, free of ice and not be too steep (slope of less than 30 degrees), and end with a flat runoff.

Please note that sledding in New Castle requires children to wear helmets.  


Top Pick: Gedney Park 

155 Millwood Road

The Town of New Castle has gone to great lengths to make sledding fun and safe at the legendary Gedney Park. There are several sledding spots although the most popular is the large, designated sledding hill that has now been fenced in, regraded, and has hay bales to make for soft stops.  Helmets required.

Our crowd-sourced recommendations for sledding in Chappaqua also include spots perfect for the littles including the small hills of 7 Bridges, Grafflin, and Bell schools.  Nearby St. Mary the Virgin Church also has a good slope for newbie sledders.

Mount Kisco

Mount Kisco Country Club

10 Taylor Rd, Mt Kisco

Leonard Park

104 Main St, Mt Kisco

Captain Merrits Hill 

Mountain Ave, Mt Kisco

Mount Pleasant

Rockwood Hall State Park 

Phelps Way, Pleasantville

*Better for older children

Rockefeller State Park

125 Phelps Way, Pleasantville

Carroll Park

202 Kensico Rd, Thornwood

Hawthorne Elementary School

225 Memorial Dr, Hawthorne

Other crowd-sourced recommendations for little sledders include Broadway Field by Hawthorne Commuter Parking and the easy hills behind Valhalla Methodist Church.

Westchester County & Slightly Beyond

Ward Pound Ridge Reservation - Pell Hill

NY-121, Cross River

Paid parking on weekends, free parking weekdays

*Considered some of the best hills in the county

Publisher Pick: Croton Gorge Park

35 Yorktown Rd, Croton-On-Hudson

Great for all ages, variety of hill sizes

Publisher Pick: Bear Mountain State Park


Great for all ages, easy to spread out, open areas, range of hill sizes

FDR State Park



Roads too icy for driving to a nearby spot?  Check out these tips for making your own snow fun!

What to do when your day of sledding is done?  Warm up with this hot cocoa recipe or make Frozen Hot Cocoa Ice Cream to keep the cold fun going!

Bonus Feature: Tubing Day Trips

By Lisa Dunleavy

Snow Tubing is fun for kids of all ages (and adults!). Some of these mountains have options for young children, others have height restrictions.

For more winter fun, check out our Ice-Skating Guide

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