Story of the Week: Milestones on the Journey

As Jon Haddenham walked across Colorado Springs with a group of graduating high school senior guys, he began to see fresh facets of the ministry of Jesus.

As Jon Haddenham walked across Colorado Springs with a group of graduating high school senior guys, he began to see fresh facets of the ministry of Jesus.

For three days, Jon shepherded the students from one end of the city to the other, traveling 36 miles between the four Woodmen campuses in the Pikes Peak region: Woodmen Heights, Downtown, Rockrimmon and Monument.

The trek created ample space for honest conversations. Students shared about their fears and prayers and the transition from high school into adulthood. It reminded Jon of the way Jesus walked with His disciples, teaching and preparing them along the road.

Jon’s pilgrimage with the students was another milestone on a journey God has been leading him on for years.

HEARTACHE AND HELP

Jon didn’t grow up in a Bible-believing household, yet he accepted the Lord as a fourth grader after a friend invited him to church.

Jon’s brother passed away when he was just 13 years old. Jon felt the weight of this deep heartache and carried it with him through his teen years.

At one of his lowest points, Jon cried out to God — and God responded. The Lord led him to a Christian school in Oklahoma, where he was blessed through his involvement in college and international ministry.

After spending time in Wyoming, a job opportunity brought Jon to Colorado Springs. While staying with a family in Black Forest, he was introduced to Woodmen. Seventeen years later, Woodmen remains his church home.

PILGRIM PEOPLE

Through each move and season, God continued drawing Jon closer to Himself. Eventually, Jon’s discipleship journey led him to explore more intentional, ancient practices of prayer and pilgrimage.

Jon points out that throughout Scripture, God’s people are often on the move. Abraham left what was familiar and traveled toward a new land, trusting God to guide and provide. Jesus walked from place to place with His disciples. Jon began to see Christians as “pilgrim people” — people learning to trust God as they journey toward their true home with Him.

A SEASON OF LISTENING

The idea for a Woodmen campus walk came to Jon during a transitional season. After years of pouring into others, including serving and discipling students and others, he was beginning to feel weary. He saw this pilgrimage as a way to mark the close of one season and the opening of another — a passage from a period focused on leading, to a time centered on listening.

In September, 2025, Jon tested a route connecting Woodmen’s campuses. Step after step, he prayed over each campus and cried out to God for the city’s broken places.

The experience inspired him to invite six students to make the journey with him in April, 2026: Gavin Kruse, Logan Schaff, Josh Farmer, Jacksun Wesson, Connor McClellan and Isaac Taylor.

The group gathered at Heights on the first morning and prayed over one another before setting out. Along the route, Jon encouraged the students to spend time in contemplation, listening to God and praying over their city.

WALKING TOGETHER

The journey challenged the students in different ways. Gavin, who naturally walks quickly, sensed God inviting him to slow down and notice what was around him.

Jacksun is blind, so the students took turns guiding him, helping him navigate the terrain. “It’s humbling to guide someone,” Jon shares. “It’s a realization of the dependence we have in life. A lot of us walk blind and don’t know it.”

Walking beside Jacksun reminded Jon and the students of their dependence on God — and of their responsibility to care for others along the way.

At the end of day one, the group reached Woodmen Downtown. They shared dinner and celebrated with ice cream. The next day, they continued to Rockrimmon before gathering at Jon’s home for steak, fellowship and worship.

By the third morning, the physical strain had taken its toll. Only three students were able to complete the full journey.

Gavin woke up sore, but Philippians 4:13 came to mind: “I can do all things through Christ who strengthens me.” He prayed for strength and continued walking.

After attending the 9 AM service at Rockrimmon, Jon and the remaining students began the final stretch toward Monument. They arrived in time for Students United, the Woodmen Students event kicking off the summer.

THE ROAD AHEAD

The pilgrimage tested the students’ strength and discipline, but Jon knew completing every mile wasn’t the only lesson.

“Sometimes we set out to do stuff, and some of us run out of oil,” he says. The journey revealed how easily life can drain us — and how deeply we need God and one another.

For Jon, it also brought together themes God had been weaving throughout his life: movement, dependence, healing and trust. As people on pilgrimage, the road may be difficult and the destination may feel distant. But God remains faithful through every mile.

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