By Eileen Shiffrin
Photo above by Megan Haley
Berkshire Beginnings
Growing up and learning to ski here was a unique and formative experience. All of our outdoor sports existed in the most beautiful setting, with the Berkshire hills as the backdrop and a peacefulness that was hard to match but easy to take for granted as kids. The winters could be magical and exciting, but also brought challenges. Back then we had storms that would heap snow to the top of our wood-sided station wagon. I don’t remember it raining as much back then in the winter, but it did sometimes. We defied the fickleness of the weather by piling on our layers and heading out to ski anyway. We didn‘t have the high-tech waterproof fabrics that we have now, so our day or evening would come to an end when we were drenched through to our skin and freezing to death.
In the fall, soon after Halloween, when the world-renowned autumn foliage would be nearing its end, my parents would start our skiing craze by bringing us down to the Besse-Clarke Sporting Goods store on North Street, usually on a dark and chilly fall evening, to get new ski gear and clothing if we had outgrown old gear. Soon thereafter, the local ski areas would start making snow during the cold nights and the season would begin.
My earliest memory of skiing was when I was maybe about 5 years old, traipsing after my brother, P.J., through quite deep snow in the cow pasture across the street from our house, to a short, steep hill where my brother (always the adventurer), neighborhood friends, and I (not much help), would pack down the hill with our skis. We would ski down, hiking back up for the thrill of even 5 seconds of descending again. That’s how much everyone loved skiing.
Lanesborough had four different small ski areas within about a 20-mile radius from our house. We skied most evenings after school and every weekend all winter long. We could be dropped off, by the bus, on the way home from school. But if we didn’t alpine ski after school then we were probably nordic skiing, on the cross-country trail at Mt. Greylock High School, preparing for our Nordic races. We had enough snow back then to easily host Nordic races at multiple venues within Berkshire County. One way or the other, we skied a lot.
The mercurial weather in the fall and winter created a naturally water-injected, hard surface at the ski areas, which we kind of hated but was good for us, it turns out—and it’s impossible to replicate in the more chic, sunny ski resorts of the world. That is how we all learned to carve turns on “blue ice.” Any other surface, anywhere in the world after that seemed like butter to us. In fact, most of the ski areas Mikaela races at (unless it’s Killington), have to literally put water into the surface in order to create the hard snow we grew up learning to ski on. That challenge instilled a type of grit in all of us that is impossible to teach kids other than experientially.
The atmosphere and environment we grew up in, with its beauty and challenges, left an indelible mark on all of us. The good days were great, so inviting and bewitching that they more than offset the cranky weather days. We grew to appreciate the small things in life, like going home to a nice hot shower, dry clothes, a pot roast dinner, and the “Wide World of Sports” on TV.

The family gathered at The Red Lion Inn in Stockbridge. Standing: Jimmy Ryan, Cara Herrick, Joe Condron, Mikaela, Polly Condron, P.J. Condron, Taylor Shiffrin, Jeff Shiffrin, Katie Condron. Kneeling: Annie Herrick, Eileen Shiffrin, Caroline Ryan.
Something that is hard to explain or describe is the deep passion for the whole alpine and Nordic lifestyle that seeded itself in us, in the Berkshires, at young ages. P.J. and my older sister, Annie, participated in a more formal ski program than I did, and they began their dryland program every fall by hiking up Mount Greylock with their team on the weekends. As I approached middle school, Annie would urge me to join the hikes, which I found intimidating (and which she always won). But I did the hikes enough times to remember the pain and also the gratifying sense of accomplishment when we got to the summit.
We moved our family from Colorado to New Hampshire when Mikaela and her brother Taylor were young, for my husband’s work. During the six years we lived there, our family had much easier access to the Berkshires. Mikaela and Taylor spent enough time in Lanesborough—at the home I grew up in with their grandparents, aunts, uncles, and cousins—to develop the same appreciation for the lifestyle.
I love to be active when we come to the Berkshires. Luckily, my siblings are of like mind. In the summer we like to play golf, tennis, boat on the lakes, hike the many trails in the area, sit on the lawn at Tanglewood, of course, bike the gorgeous Ashuwillticook Rail Trail, and visit the Clark Art Institute or the summer theater in Williamstown. With Mikaela having to work out every day, when we are visiting the Berkshires together, we often find ourselves at Bousquet Sport for tennis or the amazing gym. Then we might go have a bite at Bousquet Lodge, where the atmosphere—with a view of the ski hill—and food are great. There might be music, as well.
Another favorite is the restaurant at the top of Mount Greylock, Bascom Lodge. The food is always delicious and the views are spectacular. There’s a plethora of fun things to do in the Berkshires, rain or shine. The only problem is choosing how to spend the time we have there!

Mikaela and Eileen at Killington
Raising a Champion
My husband Jeff and I were never parents who jumped the gun. We knew that, with all sports, kids remain big fish in small ponds usually forever, but the process is still key and fun. By the time Mikaela had fairly dramatic results in her first real international race in Italy, we started thinking she might be competitive on a more global scale someday, if each of those kids predicted their nation‘s future results. But even then we kept things in perspective and understood it was a junior race. So many things can change between those young ages and the real top level of World Cup skiing, so we put the encouraging results in their proper place and got back to work with the skiing.
Raising and coaching Mikaela was the easiest thing because she was always agreeable, about everything, enjoying life all the time, and absolutely craving instruction and feedback. Her interest in learning, improving, and excelling was like no other. She was like a sponge—and demonstrated exactly what we would tell her to do. She had no issue skiing to repeat the same thing over and over: the ideal student. But I was always her mom, first and last.
Why Sports Matter
I believe sports, including body movement or physical challenge of any sort, is important for humans. We all need to care for our minds and bodies. They work together for us and neither should be neglected. Sports help kids move, get blood flowing to the brain, help to relieve mental stress, and help increase endorphins, which can help calm and center a person. Physical fitness is empowering, and helps with self-esteem.
With the passing of Title IX in 1972, girls now have equal opportunity and access to all sports—so girls, go out there, see which one suits you, and have at it. For boys as well as girls, a sport’s biggest gift initially is just the movement involved, helping kids to take care of body and mind. Then see where it goes from there.

