Kay Chester leads a horse with a rider

A Boost for Tomorrow’s Teachers: Kay Chester

Kay Chester has heli-skied in Canada, raised horses, flown a jet and helped manage a family-owned empire of Harley-Davidson dealerships that stretches from Fort Lauderdale to the Grand Tetons. Yet there’s a part of her that’s always been wistful for a chapter in her life that she never got to fully pursue: teaching.

“I would’ve liked to have tried my hand at it,” says Chester, who earned a bachelor’s degree and a teaching certification from Georgia State in 1969 but started raising a family before she could begin a career in education. “I think it would’ve been interesting to have a class that I really interacted with and got to know.”

Not that Chester, who’s spent the last 25 years enjoying the breathtaking scenery and outdoor activities of Vail, Colo., has many regrets about her life. But she does remember the challenges she faced working her way through school while starting a family — and she says she’d like to make life a little easier for future College of Education & Human Development students in similar situations. That’s why she recently endowed the Kay Chester Scholarship for Teachers in Training.

She’s Come a Long Way — but Hasn’t Forgotten Where She Started

Chester, who grew up in an “airline family” in College Park (“The area where we lived is now a runway, I think,” she says with a chuckle), started college in the summer quarter of 1965 and got married that August. Her husband attended classes at Georgia Tech while she went to what was then called Georgia State College, and they both worked their way through school — her first taste of the challenges a “working couple” could face.

“I was determined to finish my education, and I did, but I worked a number of jobs. I was your Southern Bell information operator, back in the days we were plugging in the cords. I would work at department stores — whatever, whenever, wherever the job came up and whatever season it was, I would be there. We were on the quarter system then, and quarterly admissions cost something like $250. Today, that’s nothing, but back then it was a lot.”

Reflecting on those hectic days as a working student, Chester decided to endow a scholarship with a specific sense of purpose. If all other selection criteria for the Kay Chester Scholarship are equal, preference will be given to a female College of Education & Human Development student who is raising a family while pursuing her degree.

“When I got divorced just recently, at age 65, I thought through my life and I remembered that period of my life where money had been sketchy,” she explains. “And I thought, ‘If I can help some working woman who’s trying to go to school while she’s working and she has a family, that’s what I’m going to do.’ This is my first step into that.”

The endowment has particular meaning at Georgia State, Chester adds, because of the accommodations that the university provided for female students like her who were having the “non-traditional” college experience. “I was obviously not sorority material,” she laughs, “but there was a group called MRS [Mu Rho Sigma], a sorority that developed for married women, and most of us were working, of course. We had a room that we could go to, and I understand it’s no longer there, but it was a place that we could collect ourselves, we could visit with each other, we could share experiences, and that was a very important part of my college experience. Partying was out for me since I was working, but this was a little getaway, and it was fabulous. I wish they still had it.”

A Life Filled With Blessings

With a major in English and a minor in Spanish, Chester earned her degree in 1969. Just a short time later, she found out she was pregnant with her first child — at a time when it was rare for expecting mothers to be hired for any kind of job, teaching included.

Even with her teaching career sidelined, though, Chester found fulfillment in other ways. One was by helping her husband build a series of businesses around the country; another was by hitting the slopes.

“Our first trip to Vail was in ’67,” she says. “We had learned to ski at Maggie Valley, N.C., and we’d tried Sugarbush and Beech Mountain, so we thought, ‘OK, let’s try the West.’ Well, we fell in love with it. So skiing is what brought us here — the lifestyle, the security, the friends, everything.”

The Chesters bought a vacation home in Vail in 1980 and moved out to Colorado full-time eight years later, around the time her oldest son, Craig, graduated from high school. Both Craig and her younger son, Cliff, earned degrees from the University of Colorado, helped run the family businesses and eventually bought houses in Vail themselves. “I have this wonderful circle of friends here,” Kay says, “and now my family’s here. Both boys have homes here — one is part time and one is full time. And I’m just so blessed that they’re here with me.”

These days you’re more likely to find Kay Chester sporting jodhpurs and riding boots than skis. “I’ve been into horses for a number of years, Paint Horses in particular, so that’s my passion right now,” she says. “I’m learning dressage and I have a couple of hunter-jumpers, so we have a good time with that.

“I have girlfriends who are involved with that too, and I have a great group support here. It’s amazing. People think that in a resort community, you don’t have everything that you need, but you know what? If you’ve lived here and it’s your home, it’s truly amazing how special it is. And we have a special environment, temperatures, beautiful scenery, and special people that make it great.”