
Kelsey Julia Boleski left us on March 3, 2024 in Crested Butte Colorado at the age of 34.
An avid athlete, outdoorswoman, skier, biker, horsewoman, animal lover and creator of circles of friends which overlapped and connected people across the country. Kelsey was funny, moody, busy, driven, tenacious, adventurous, loving, loyal and honest about her struggles with mental health.
Kelsey started crawling at six months old and walking at nine months and started running shortly thereafter. She never looked back. She started skiing at Mad River Glen and Sugarbush took a year off in fourth grade to skate, cross country ski and snowshoe. She played soccer, field hockey, lacrosse and was very good at golf but did not care for it. She was a member of the Mad River Glen Free first female free ski team and had dreams of competing but finances made that dream impossible to follow.
Born in Burlington in 1989, Kelsey attended Fayston Elementary School and Harwood Union. She studied equine management at Montana State University. After a stint in the west, she returned to Vermont and the Outdoor Gear Exchange in Burlington where she excelled at mountain bike repairs, ski tuning, engineering, fixing and fitting and making stuff work She enjoyed board games, Suduko, training, skiing, camping and riding with friends.

Returning to the west, Kelsey got her dream job working for a ski company but Covid hit and it was a challenging time and that dream was shattered. It was a hard time but Kelsey fought her way back to land on her feet and ended up in Crested Butte where she connected with special new friends customers, coworkers, cross fit enthusiasts, bikers and skiers and they supported and loved her. Kelsey was rarely loved animals. Her very best friend was her dog Smith, the Newfie who shared her adventures from Montana to Vermont and her cat Bennie and her cat Carla named after her teacher Carla Lewis. Her canine friend when she passed was two year old 115 lb Alaskan Malmute named Bennie who is now with her mom.
To honor Kelsey’s memory, family and friends are holding a celebration of her life on June 2, 2024 at The Round Barn in Waitsfield from 1:00 PM – 4:00 PM . We invite anyone who knows her or her family to attend and remember her busy, brave, complicated, messy, amazing, beautiful life. Please be prepared to eat Macaroni and Cheese and participate in a sing along of favorite Disney tunes.

Kelsey leaves behind her mom Michelle Boleski of Hartford Vermont, her dad Jack Wilkins and his wife Karen of Morrisville Vermont. Her Aunt Janet and Uncle Bruce Godin, Aunt Gwyn and her Uncle Randy Mandigo and Uncle Michael Siska Jr.(Ronnie).
She leaves behind her amazing cousins, Austin R. Mandigo (Anna) Ross M. Mandigo (Caroline) Logan M.Siska (Jennifer) Shawn M. Siska, Erika G.Taylor(Jay) and Erin G. Bovat (Nathan) and her second cousins whom Kelsey adored! Aubrey Mandigo Wilkins Siska Landon R.Miller and Brooklynn B Miller.
Kelsey leaves behind her Mom’s cousins Pat and Jerry McKenna, Karen and Jim Parker, Mary Jane Jennings and her partner Will, Dennis and Barb Ryan, Sandra Jennings, Colleen Jennings. John Jennings, Brendan McKenna and his wife Kelly and their two daughters and Austin McKenna and his wife Windsor and their daughters.
Growing up it takes a village and Kelsey also had some great “horse moms”, Janine McClain and Meg Hilly. She was in love with horses from the first time she laid eyes on them and found kindred souls and mentors in these ladies. She some powerful ski mentors, Anna, Kim, Katie and Karen and other women who taught her to be fearless on the mountain and to “ski like a girl”.
She leaves behind many circles of amazing friends who loved her, was frustrated with her, recreated with her, cried with her, found adventures with her and supported her.
The family is grateful for the love and support of her friends our friends and the circles of community she connected.
She was predeceased by her beautiful and loving Aunt Ricarda W. Siska, Grandma Lois and Grandpa Richard Wilkins, Grandma Ethel Boleski and grandpa Larry Boleski, Great Aunt Lil., Smith the Newfie, Bennie the cat, Emma, Copper, Grady, and Carla the cat who are waiting to greet her over the Rainbow bridge.
There is a GoFundme page to help with costs of the celebration of Life, Care for her dog Bennie and to lay the foundation for a scholarship to help disadvantaged girls play sports and thrive.
