Jed Bowman, superintendent of Woodland Park School District RE-2, will leave his post at the end of this school year in May, he announced Friday.
Bowman cited "health concerns for his wife" as the reason.
"As Colorado natives, our family struggles with the idea of leaving and at the same time, we have such strong faith that we know everything will work out," he said in a statement. "Our time in Woodland Park would best be described as treasured - we love the school district, community, living here and opportunities for students."
Bowman has headed RE-2, which consists of one high school, one middle school and three elementary schools, for eight years.
He won the 2015 Colbert Cushing Award for outstanding professional contributions and service to the field.
He served two terms as president of the Colorado Association of Superintendents & Senior Administrators, a department of the Colorado Association of School Executives.
In response to Bowman winning the award, Karen Brofft, superintendent of Lewis-Palmer School District 38 called him "a leader of distinction," and said Bowman brought "incredible expertise, humor, talent and a genuine concern for each individual to the position."
RE-2 board president Carol Greenstreet said members have appreciated his skills.
"Under his leadership, our district has creatively expanded student learning opportunities in the face of considerable budget cuts," she said.
The district successfully prevailed in an unusual ballot funding initiative in April 2016, which increased the city's sales tax to benefit schools.
Bowman's children have attended Woodland Park schools, and Greenstreet said "the entire family will be missed."
The five-member board will initiate in December a nationwide search for a replacement for the leadaer of the 2,500-student district in the small mountain town of Woodland Park.