The Long Way Home: A Winter Odyssey and the Roadmap for 2026

Date: January 6, 2026

Location: Biddeford, Maine

Mood: Grounded

The Christmas tree is still standing in the corner, but the lights are off. The bags are unpacked. The "Out of Office" auto-reply has been turned off.

Usually, the first week of January feels like a hangover—a jarring snap back to reality after the holiday haze. But this year feels different. This year, we didn't just "take time off." We went on a journey.

We didn’t fly south to chase the heat. We drove deeper into the storm. From the salt-slicked streets of Portland to the deep woods of Twin Ponds, this vacation wasn't about itineraries or reservations. It was about the Art of the Pivot. And if the last ten days were any indication, 2026 is going to be the year we stop fighting the weather and start learning how to dance in the snow.

Here is the story of our long way home.

The Christmas Eve Audible: The Old Port

Tradition dictates that on Christmas Eve, we head north to Jackson, NH. But this is New England, and Mother Nature doesn't care about your Google Calendar. As the snow started to pile up, the roads north looked treacherous.

So, we called the first audible of the trip. We kept it local. We drove twenty minutes north to Portland’s Old Port.

If you’ve never walked these cobblestone streets during a fresh snowfall, you haven't really seen Christmas. The crowds were gone, scared off by the forecast. It was just us, the red brick buildings dusted in white, and the smell of salt air mixing with woodsmoke. It felt like stepping into a Charles Dickens novel. We didn't get the sleigh ride we planned, but we got something better: a quiet, snow-globe city all to ourselves.

The Sunday Drive: Lovell and the Western Woods

After the wrapping paper was cleared, the itch to move set in. We took the car west toward Lovell, Maine.

This is the Maine that people forget about. It’s not the coast, and it’s not the ski resorts. It’s "Stephen King Country"—winding roads that snake around frozen lakes, endless pines, and silence so heavy you can feel it in your chest. We found a spot where the cell service died and the notifications stopped. For a few hours, the world wasn't a list of tasks; it was just a windshield framing a perfect winter day.

The Siege at Twin Ponds: The New Year's Gift

For New Year's Eve, we checked into Twin Ponds Lodge. The plan was simple: a quick getaway to ring in 2026. But then the storm hit.

We were supposed to leave, but the snow had other ideas. The roads were covered. In a past life, I might have panicked about getting back. This year, we just poured another coffee. We stayed an extra night.

Waking up on Friday morning, January 2nd, was the highlight of the entire vacation. The world was completely erased by white. The world felt still, just the rhythmic scraping of a plow somewhere in the distance. That extra night wasn't a delay; it was a bonus level. It forced us to sit still, watch the snow fall, and just be.

The Grand Finale: Black Mountain

By Sunday, January 4th, the cabin fever had broken, and I needed to move. I aimed for Wildcat, but 50mph winds slammed the door shut.

Time for the final pivot. I headed to Black Mountain in Jackson.

This was the perfect bookend to the trip. I spent the day lapping the Red Chair—a fixed-grip double that moves at a conversation pace. No high-speed quads, no lift lines, just 8,000 vertical feet of honest New England skiing. It was cold, it was windy, and it was absolutely perfect. It reminded me that you don't need the biggest mountain to have the best day; you just need to show up.

The Re-Entry: The White Barn Pasta

I arrived back in Biddeford Sunday night—windburned, tired, and hungry. The old me would have ordered takeout. The "Country Road" me looked in the pantry.

I whipped up what I’m calling the "Rustic White Barn Pasta"—a $4 hack using canned corn chowder, bowties, and plenty of black pepper. We ate it on the couch, watching The Holdovers, with the Christmas tree lit for one last night. It was the best meal of the trip because it was simple, warm, and earned.

The Manifesto for 2026

As I sit here writing this, ready to log back into the corporate world, I don't feel the usual post-vacation dread. I feel optimistic.

This trip taught us that the best moments happen when the plan falls apart.

• The snow canceled the sleigh ride, so we found magic in the Old Port.

• The storm trapped us at the lodge, so we found peace in a snow day.

• The wind shut down the big mountain, so I found soul at the small one.

2026 is going to be the year of the Pivot. We aren’t going to force things. We are going to adapt. We are going to prioritize "Old School" values—cooking at home, fixing the old house, skiing the independent hills, and finding value in the "nooks and crannies" of life.

The vacation is over. The tree is coming down. But the light? The light stays on.

Happy New Year, everyone. Let’s get to work.