Tall Timbers: 25 Years of Growing Roots in Colorado Springs

A Family Legacy of Stewardship, One Tree at a Time

Twenty-five years ago, Dave and Debi Carpenter had a simple vision: to care for the trees that make Colorado Springs beautiful, one neighborhood at a time. Armed with a single chainsaw, a truck, and an unwavering commitment to their community, they planted the seeds of what would become Tall Timbers Tree & Shrub Service on August 1, 2000.

What began in their basement home office with Debi managing the business while caring for their two young boys, Cory and Trevor, and Dave knocking on doors in their own neighborhood for estimates has grown into something far greater than a tree service company. It’s become a testament to the power of deep roots, both literal and metaphorical.

From Humble Beginnings to Community Cornerstone

The Carpenters' journey reads like a love letter to the American dream, written in the language of hard work and community dedication. In those early days, Debi would field calls from their basement while the boys played nearby, scheduling jobs and managing the growing business. Dave would come home each evening, chainsaw oil still on his hands, to help with homework and plan the next day's work.

By 2001, their reputation for quality and integrity had spread beyond their neighborhood. Landing a significant city contract to remove junipers along Academy Boulevard marked a turning point they could finally hire two full crews. It was the first sign that Colorado Springs was taking notice of this young company that treated every tree, and every customer, with genuine care.

The subsequent years tell a story of steady, purposeful growth that mirrors the very trees they tend. From a rented lot with a Conex office on Bott Avenue in 2005, to a garage and scrap yard on Nevada in 2006, each move represented not just expansion, but deeper roots in the community they served.

Building More Than a Business

In 2007, they launched their Plant Healthcare Division, recognizing that true tree care goes beyond pruning and removal. Deep root watering, fertilization, and pest control became part of their comprehensive approach to urban forest stewardship. They stayed current with the latest arboriculture technology, always seeking better ways to serve both their trees and their community.

In 2008, Tall Timbers found its permanent home on High Street a small house and lot that Dave and Debi rented, then purchased in 2010. It was here that their vision truly took shape. The construction of their 6,500-square-foot warehouse and office building in 2015 wasn't just about business growth; it was about creating a lasting foundation for the community they'd committed to serve.

"Dave always said we weren't just cutting trees we were nurturing the urban canopy that makes our city livable," reflects the family. This philosophy became the heartbeat of everything Tall Timbers did.

A Vision That Outlives Its Creator

Perhaps no initiative better captures Dave Carpenter's heart than the ROE Project, launched in 2020 with the motto "Rejuvenate Our Earth One Tree at a Time." This wasn't a marketing campaign it was a calling. Throughout each planting season, Tall Timbers gifts trees to commercial and residential customers, understanding that the best business model is one that gives back to the community that sustains it.

The project embodied Dave's belief that their success was inextricably linked to the health of Colorado Springs' urban forest. Every tree planted was an investment in the community's future, a living legacy of care and stewardship.

Tragically, Dave Carpenter passed unexpectedly in the spring of 2024, leaving behind a community that had been enriched by his vision and a family business built on his values. But like the trees he spent his life nurturing, his legacy continues to grow.

Rooted in Family, Reaching Toward Tomorrow

Today, Tall Timbers stands as one of the leading tree services in Colorado Springs and neighboring areas, employing 40 dedicated professionals and operating a fleet of 22 trucks, two stump grinders, and a large grapple truck. But these numbers tell only part of the story.

The real measure of their success lives in the leadership transition that seamlessly continues Dave's vision. Debi Carpenter, along with their sons Cory and Trevor the same boys who once played in that basement office now lead the company alongside Brad Williams, who has been part of the Tall Timbers family since 2013.

"We're not just preserving Dad's legacy," says the family. "We're continuing his mission to be true stewards of our community's natural beauty."

More Than Service A Covenant with Community

As Tall Timbers celebrates 25 years of service, their story resonates beyond business success. In an era when corporate giants often dominate local markets, Tall Timbers represents something precious: a company that grew up with its community, that understands the value of relationships that span decades, and that sees each tree as part of a larger ecosystem of care.

From that first neighborhood estimate to today's comprehensive urban canopy management, Tall Timbers has remained true to a simple principle: healthy trees make healthy communities. They've weathered storms both literal and metaphorical always ready to respond when their neighbors needed them most.

Their customer relationships aren't just transactions; they're partnerships built over years of trust. Many clients have watched the Carpenter boys grow up, seen the business evolve, and remained loyal because they know they're supporting something bigger than a service company they're supporting stewards of their community's natural heritage.

Growing Forward

As Tall Timbers looks toward the future, they carry forward Dave's vision with the wisdom that comes from 25 years of deep community roots. The ROE Project continues, gifting trees and "rejuvenating our earth one tree at a time." Their commitment to staying current with arboriculture advances ensures Colorado Springs benefits from the latest in tree care science.

But perhaps most importantly, they continue to approach each job with the same care and personal attention that Dave brought to those first neighborhood estimates. Whether it's emergency storm response, preventive plant healthcare, or simply helping a homeowner understand the best care for their backyard oak, Tall Timbers treats each call as an opportunity to strengthen the bonds between community and canopy.

In a world that often feels increasingly disconnected, Tall Timbers stands as a reminder that some of the most important work happens quietly, consistently, and with deep respect for the natural world that sustains us all. They are more than a tree service they are guardians of the green spaces that make Colorado Springs home.

As they thank their loyal customers for 25 years of trust and support, Tall Timbers looks forward to continuing their mission: one tree, one customer, one community at a time.