Skiing and Painting the Vermont 20

Posted by Carrie Pill on

Skiing and Painting the Vermont 20

Hi there. My name is Carrie Pill. This winter I challenged myself to skiing and plein air painting all of Vermont's 20 alpine ski areas and now that the season is winding down, it's time for a recap!

The Person

I am a professional artist and passionate skier with a love for discovery, community and sharing. I wanted to ski all of Vermont's ski areas and tie it into my work, as a result, 'A Painted Tour' was born.

The Challenge

I set myself a goal for the 2022/2023 winter: to ski and plein air paint all 20 Vermont alpine ski areas. Some amazing partners helped me acheive my goal. Thank you Ski Vermont, Stio and the Vermont Department of Tourism.

Carrie Pill Ski Paint Vermont


A typical day on 'A Painted Tour'

  • Wake up. Breakfast. Pack up car. Go!
  • Arrive. Bundle up. Walk, take lift or ski to painting spot.
  • Paint for a couple hours.
  • Break. Warm up in lodge. Refuel. 
  • Transition. Put painting materials in car. Change gear if needed.
  • Ski. Sometimes with a buddy. Cover as much ground as possible. Take notes, pictures and video. 
  • Apres. Sometimes with a friend. Sometimes another painting session.
  • Dinner. Often times back at the room or home. Sometimes at a local spot. 
  • Bring paints and paintings inside. Wash brushes. Hot shower. Hang up ski gear. Plug in electronics. Set up for the next day.
  • Share. When time and energy allowed, I would create a post or video from the day.
  • Sleep. Repeat!
Watch a short video of a typical day: Quechee Club

Getting There 

Many of these visits began with a scenic drive. What is it about the open road that ignites introspection? I indulged, decompressing while taking in Vermont's most iconic roads: Route 100 N, Route 7 South, 116...

Painting Warm

Upon arrival I would throw on my warmest gear, preparing to paint first and ski second. I discovered from previous plein air days that painting before skiing was the driest, warmest and smartest approach.

You can imagine my struggle of fighting the urge to grab first chair. Once that brush was moving though, I could easily let that sense of urgency go.

plein air painting Vermont


"How did you decide where to paint?"

Before arrival, I might have a hunch about where I'd like to paint that day. On more than one occasion, a lift hold, poor visibilty or precipitation would force a pivot. This included painting inside a base lodge, inside the car or at the base of the mountain.

"Doesn't the paint freeze?"

Oil paint is a rugged friend. You can count on oils to come out and move around in the cold with you. Would they eventually freeze if left cold enough, long enough? Absolutely.

My paint box typically moved from a heated vehicle or room to my backpack to the easel. This ensured that the paints started warm. Most of these plein air sessions did not exceed four hours. The coldest painting session I did was -7 degrees farenheit. These mighty paints were up for the task.

When the easel went up...

I was pleasantly surprised by the curiousity and enthusiam that I was met with. Painting is typically such a solitary activity. 

People asked questions, took pictures and watched the process. Some folks stopped by after each lap to see the progress, others shared fondest memories and favorite facts about the ski area.

Thank you if you for stopping by. You gassed me up and made me feel at home.

Carrie Pill Painting Burke


"What was the favorite place you visited?"

This question is tricky as I have my home favorite: Pico Mountain. There were ski areas that surprised me, naturally, those ones stick out in memory. Who doesn't love it when an experience delivers above and beyond?

I keep coming back to the fun I had at the hills, that is, the itty bitty ski areas. These were the unexpected incredible ski experiences. Rope tows, cheap tickets, handmade signs, fire pits, jeans, $1 hot cocoas, T-bars, classic rock blaring and packs of kids cutting loose.

It was wholesome, nostalgic, community-supported and felt like home to me. I treasure my memories at Lyndon Outing Club, Cochran's Ski Area and Northeast Slopes.

Of course I happy danced... powder days at Stowe, to waterpark apres at Jay and rockstar Bolton tree runs. The variety of ski and snowboard experiences and terrain that Vermont offers is vast and vibrant. 

Carrie Pill Skiing Vermont


Your Mountain Communities

Even the largest of Vermont's ski areas had a sense of community. Skiing and painting the Vermont 20 was an opportunity to get out of my comfort zone. I was often that awkward girl traveling, skiing and painting alone. I am so grateful for the locals who were willing to meet up with me. This deepened my appreciation and understanding of our ski areas. Thanks friends!

Watch short video: Tour friends


Skiing and Painting VT Tour Stats

  • 65 season ski days to date (as of 4/24)
  • 34 paintings (and counting): including 3 studio, 1 interior and 3 nocturne paintings

An Unforgettable Season

Now here we are, brushes are clean, most of the paintings have found homes and my warmest gear is now stowed away.

It flew by. What surprised me was the energy. I thought it would be a struggle to motivate at times. Each visit instead fed me so much so that I couldn't wait for the next one.

Painting and skiing at all of Vermont's ski areas was an absolute joy and a privilege, but it was not without its challenges. Yours truly found herself humbled on some of the most technical trails and tough conditions, locked out of an Airbnb at night in a Nor'easter and emotionally wrecked after losing a pet.

Life happens. 'A Painted Tour' pushed me to figure it out when I was thrown a curve ball. When it got tough, I had something amazing to lean on: my dream project.

This is a season I will never forget. Thanks for being awesome Vermont.

Thanks for reading. I hope to see you out there! -Carrie


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