When the Hamptons gets a big snowstorm, everything slows down in the best possible way. Roads go quiet, the beach turns white, and suddenly everyone’s asking the same question:
Where do we sled?
If you’ve got kids (or you’re a kid at heart), grab your sled, pack some hot chocolate or cider, and head to one of these local favorites. These are the hills people actually use.
🛷 Quail Hill — Amagansett
Best for: Classic sledding + a little adventure
Quail Hill is a longtime local favorite, especially after a big snowfall. The hill itself is great, but part of the fun is getting there.
How to access it:
Park off the road on Old Stone Highway, then walk through the trees to reach the hill. It feels a little magical…especially when everything’s covered in fresh snow.
✔️ Wide open space
✔️ Great for a range of ages
✔️ Wear boots
🛷 The Skate Park — Montauk
Best for: Big laughs and bumpy rides
This one’s a blast. When it snows, the Montauk skate park turns into a surprisingly fun sledding spot.
Local tip:
Park at the top, not the bottom—and be ready for some bumps. This isn’t a gentle glide kind of hill; it’s more of a laugh-until-you-wipe-out situation.
✔️ Fast runs
✔️ Fun terrain
✔️ Older kids (and adventurous adults) love it
🛷 Pierson School — Sag Harbor
Best for: Community vibes and easy sledding
Pierson is the go-to for Sag Harbor families, and on a snow day, expect to see everyone there.
What to know:
It’s popular for a reason—easy access, good hills, and lots of local kids running around. Great if your kids want instant friends or you want that classic snow-day energy.
✔️ Super family-friendly
✔️ Easy parking
✔️ Lively and social
☕ Don’t Forget…
• Sleds (obviously—but trash can lids still work in a pinch 😉)
• Hot chocolate or cider
• Waterproof gloves (trust me)
• A thermos for you
Snow days in the Hamptons are fleeting—so lean into them. Bundle up, get outside, and enjoy the kind of winter magic you don’t always expect out here.
Stay warm and have fun 🤍