Robertson’s Road Trips: Our Favorite Family-Friendly Winter Getaways

January 29th, 2026 by

New England Road Trip

 

At Robertson’s GMC, we know that winter in New England isn’t just for staying indoors—it’s for loading up your Sierra or Yukon, switching into 4WD, and finding that perfect snowy destination. Whether your family lives for the ski slopes or you’re just in it for the hot cocoa and cozy fireside vibes, our region is packed with winter magic.

Buckle up as we share our top staff picks for Robertson’s Road Trips: Family-Friendly Winter Getaways!

1. Stowe, Vermont: The Ultimate Winter Wonderland

If you’re looking for the quintessential New England winter, Stowe is the gold standard. Often called the “Ski Capital of the East,” it’s a dream for active families, but there is so much more than just downhill skiing.

 

  • The Drive: A scenic trek up through the Green Mountains that your GMC was built for.
  • Family Fun: Take the kids to the Lodge at Spruce Peak for outdoor ice skating, or head to Umiak Outdoor Outfitters for a moonlit snowshoe tour or sled dog adventures.
  • Pro Tip: Don’t miss the Stowe Winter Carnival in January to see incredible ice carvings throughout the village!

 

2. North Conway & Jackson, New Hampshire: White Mountain Magic

The White Mountains offer some of the most dramatic winter scenery in the country. North Conway is a hub of activity that keeps every member of the family entertained.

  • The Drive: Navigating the Kancamagus Highway in winter is breathtaking (just be sure to check the weather reports before you head out!).
  • Family Fun: Visit Nestlenook Farm for a truly magical Victorian-style ice skating experience and horse-drawn sleigh rides. For a unique thrill, take the kids to Cranmore Mountain Resort for their famous 10-lane giant snow tubing park.
  • Sweet Treat: Stop by the Bavarian Chocolate Haus for some authentic handmade winter treats.

 

3. Lincoln, New Hampshire: Ice Castles and Alpine Adventures

Just a short hop through the Notch, Lincoln is home to one of the most Instagram-worthy spots in New England.

  • Family Fun: The Ice Castles in North Woodstock are a must-see. It’s an ethereal world of frozen towers, slides, and thrones built entirely by hand.
  • Adventure: If your family wants a bird’s eye view, Alpine Adventures offers winter ziplining—an exhilarating way to see the snow-covered forest.
  • The Ride Home: After a day in the cold, the heated seats and steering wheel in your GMC will feel like a luxury spa.

4. Kennebunkport, Maine: A Coastal Winter Escape

Think the coast is only for summer? Think again. Kennebunkport trades the crowds for a peaceful, “Norman Rockwell” kind of charm in the winter months.

  • Family Fun: The Waterhouse Center offers a covered outdoor ice skating rink that is free to the public. For a unique dining experience, book a “fish shack” at Batson River Brewing—private, heated small cabins where the family can enjoy a meal together.
  • Coastal Views: Take a slow drive down Ocean Avenue to see the winter Atlantic crashing against the rocks.

5. Stockbridge & The Berkshires, Massachusetts: Cultural Cozy-ness

For a road trip that’s a bit closer to home but feels worlds away, the Berkshires offer a refined winter pace.

  • Family Fun: Visit the Norman Rockwell Museum to see the art that defined the American winter. For some outdoor action, Bousquet Mountain is great for family-friendly skiing and tubing.
  • Winter Lights: If you time your trip early in the season, NightWood at The Mount (Edith Wharton’s home) is an incredible immersive light and sound experience through the winter woods.

Ready for the Road?

Before you head out on your winter getaway, make sure your vehicle is as ready for the adventure as you are. From tire pressure checks to ensuring your antifreeze is topped off, the Robertson’s GMC Service Department is here to get you road-trip ready.

Where is your family heading this winter? Tag us in your photos using #RobertsonsRoadtrips—we’d love to see your GMC in the wild!

Safe travels and stay cozy!