Winter Weekend Getaways (Within Driving Distance)
From a Family Photographer in Westchester, Putnam & Fairfield County
As a family photographer based in Westchester, Putnam, and Fairfield County, I’m always drawn to places that feel magical this time of year. I especially love the kinds of spots where kids can run in the snow, parents can slow down a little, and the whole weekend feels like a memory in the making.
If you’re looking for an easy winter escape (without hopping on a plane), here are four of my favorite cozy, drivable destinations for families.
❄️ Lake Placid – Adirondack Winter Magic
If you want full-on snow globe energy, Lake Placid is it.
Think: frozen Mirror Lake, snowy mountain backdrops, and that charming Main Street that feels straight out of a holiday movie. Families can ice skate, ski at nearby Whiteface, or just wander through town with hot chocolate in hand.
Where to Stay:
Golden Arrow Lakeside Resort : it sits right on the lake and walking distance to everything. Waking up to a frozen lake is something your kids will remember. End the evening with a swim in a memorable indoor pool.
⛷ Lake George – Quiet & Cozy in the Off-Season
Most people think of Lake George as a summer destination, but winter is when it slows down and honestly, that’s part of the charm.
It’s peaceful. It’s scenic. And it’s perfect for families who want a calm, low-key weekend away. Bundle up for lakeside walks, grab dinner without summer crowds, and enjoy the simplicity of a snowy reset.
Where to Stay:
The Georgian Resort: centrally located with classic lakefront charm.
🏔 Hunter Mountain – Adventure in the Catskills
If your family loves to stay active, there’s something for every age. And even if you’re not hitting the slopes, renting a cabin nearby and spending evenings by the fire feels like peak winter.
Where to Stay:
Renting a cozy Airbnb cabin nearby makes the experience feel extra special (and gives everyone space to spread out).
✨ The Berkshires – Classic New England Charm
If your ideal winter weekend includes charming towns, local bookstores, and slow mornings, the Berkshires are a beautiful option.
It’s less about high-energy adventure and more about intentional time together. Strolling through town, visiting a museum, lingering over brunch. This is a simple and special getaway (think Norman Rockwell).
Where to Stay:
Red Lion Inn in Stockbridge is a classic for a reason; with their fireplaces, historic charm, and that nostalgic New England feel.
Why I Love Winter Getaways for Families
As a family photographer, I’m always telling my clients this: the magic isn’t in the big, perfect moments. It’s in the small ones. These weekends away create those memories naturally!
And if you’re local to Westchester, Putnam, or Fairfield County, all of these spots are close enough to make it happen without a stressful travel day.
Winter doesn’t have to feel long. Sometimes it just needs a little adventure! Go Explore!
