'The man who shaped the mountain': Remembering former Big Sky Resort COO Taylor Middleton

BIG SKY — More than 500 Big Sky community members gathered in the Huntley Dining room Saturday to celebrate the life and legacy of former Big Sky Resort president and chief operating officer Taylor Middleton.

Middleton passed Feb. 19 in his sleep at 68. He is remembered as one of the most influential figures in developing the Big Sky Resort and community.

“He was involved in everything,” reminisced Jim Ness, the former president of First Security Bank Montana and longtime friend of Middleton. “He was instrumental in everything ... he built Big Sky into what it is today.”

The memorial service included emotional speeches from Middleton’s friends and family, performances of songs, including Louis Armstong’s “What a Wonderful World”, and a bath of sounds Middleton had recorded around Montana and his home state of Alabama.

Barbara Rowley, Middleton’s wife of three decades, said the memorial was for the whole community to grieve together. She remembers her husband as someone whose life centered on gratitude, community and joy.

“On the day he died he told me, ‘This was a great day’, because that’s something he said every day,” Rowley recalled. “He absolutely never lost his smile.”

A slideshow playing at the memorial featured dozens of photos of Middleton with Rowley, their daughters Anna and Kate, friends, and community members. Middleton wore a smile in each snapshot.

Middleton’s tenure in Big Sky started in 1981, when he packed up his life in Alabama and headed toward Yellowstone. When Middleton arrived, Big Sky Resort was in its sixth year of operation.

“He loved work, he loved to play, he loved the outdoors, and he hated to be bored,” Stephen Kircher, president and CEO of Boyne Resorts, said during the memorial. “Those four things shaped a life of extraordinary purpose.”

During his time at the resort, Middleton climbed the ranks from receptionist at Huntley Lodge to sales and marketing before assuming the role of general manager in 1998. He was eventually tabbed as Big Sky Resort president and chief operations officer in 2019.

“He would never go by his title unless he was pressed or was giving a speech,” Rowley said. “But sometimes even then, he’d just go by ‘Taylor’”.

In these leadership roles, Middleton oversaw the construction of more than 20 lifts, two hotels, and two trams. Kircher remembers Middleton as “the man who shaped the mountain” and credited him with helping lead Big Sky’s transformation into SKI Magazine’s 2026 top-ranked ski resort in North America.

Middleton’s influence extended beyond the ski hill and into the Big Sky community. He worked to help develop the first Big Sky transportation district, bank, hospital, and the Lone Peak school.

He served on boards, spoke at hearings, and fostered connections that brought critical capitol into the community, said Brian Brown, senior vice president of Bozeman Wealth Management Group and longtime friend of Middleton’s. Middleton also worked to create the Big Sky Chamber of Commerce and pushed the implementation of the resort tax.

“Taylor’s commitment to the community was just how he was raised. His grandparents and his own parents were very involved in the community,” said Brown. “It was just a part of (his) fabric and a part of his DNA.

In addition to his work on the resort and community, Middleton is remembered as a loving husband and father who always kept his family busy skiing, hiking, biking and rafting.

“My dad taught me how to row a boat. On our last long river trip together, this summer on the Salmon ... his arms weren’t strong enough to row the rapids,” Anna Middleton, the eldest daughter, said. “So, I did. He looked at me and pumped his fists in the air and then started crying with pride. I crawled into his arms like I did when I was little, and we both cried.”

As Anna mourns her father’s passing, she said she is grateful to have the widespread community her father fostered to share the heavy weight of the grief.

“Over his long career in Big Sky, he built a wonderful community of friends ... and had the softest heart for them,” Anna said. “He shared his friends with me in adulthood. He gave me this community of people before he ever knew I would need them in his absence.”

An on-mountain run dedication took place after the Saturday service. Anna and Kate Middleton, both Big Sky ski patrollers, set off a “Big Sky version of a 21-gun salute,” ending a moment of silence for Middleton and signaling the unveiling of the new run’s sign. Tango Trees was renamed “Taylor’s Trees” in Middleton’s honor.

For those wishing to honor Middleton’s legacy, his family suggests making donations to the Big Sky Hospital, Big Sky Bandage or RUFF, the Boyne Forever Foundation.

“I think the best way to honor (Taylor) is by carrying on his legacy of being a good person, being a good human being, and caring for other people and your community,” said Jim Ness, the former president of First Security Bank.{/div}