Chief Trailbuilder
The Art
The Highlands Art & Tree Trail is more than a walk in the woods—it’s a carefully crafted journey that blends the raw beauty of the Niagara Escarpment with thoughtful design, artistic expression, and deep environmental respect. At the heart of this trail’s creation is master trailbuilder Jeremy Shields, whose work has turned a series of rugged escarpment trails into a seamless, story-rich loop.
The route weaves together existing hiking, biking, snowshoeing, and cross-country ski trails, transforming them into a cohesive experience that profiles the escarpment’s ancient geology, from mossy limestone ridges to glacial erratics and hardwood forests. Every curve and climb was chosen with intention—balancing accessibility with immersion, and ensuring that each turn reveals a new perspective of South Georgian Bay’s breathtaking landscape.
Equally important to the trail's design is the placement of each art installation. Jeremy worked closely with the artists and curators to create natural settings that invite pause and contemplation. These spaces aren’t just spots to admire the art—they’re sanctuaries for reflection, where visitors can absorb the textures of the forest, the rhythm of the wind, and the quiet legacy of the land. A standout feature of the trail is the handcrafted bench installations, particularly those made from a massive maple tree that fell near the 9th tee at Duntroon Highlands Golf Course during the devastating March 2025 ice storm. Jeremy and his team salvaged the tree and, with a mix of traditional techniques and modern tools, milled, shaped, and installed the slabs into sculptural seating along the trail. The process demanded a deep knowledge of wood, precision in handling large, heavy materials, and an eye for harmonizing the bench with its surrounding landscape. The result is a series of beautiful, functional pieces that pay tribute to resilience—of both nature and craft.
Equally important to the trail's design is the placement of each art installation. Jeremy worked closely with the artists and curators to create natural settings that invite pause and contemplation. These spaces aren’t just spots to admire the art—they’re sanctuaries for reflection, where visitors can absorb the textures of the forest, the rhythm of the wind, and the quiet legacy of the land. A standout feature of the trail is the handcrafted bench installations, particularly those made from a massive maple tree that fell near the 9th tee at Duntroon Highlands Golf Course during the devastating March 2025 ice storm. Jeremy and his team salvaged the tree and, with a mix of traditional techniques and modern tools, milled, shaped, and installed the slabs into sculptural seating along the trail. The process demanded a deep knowledge of wood, precision in handling large, heavy materials, and an eye for harmonizing the bench with its surrounding landscape. The result is a series of beautiful, functional pieces that pay tribute to resilience—of both nature and craft.
The Artist
Jeremy Shields
I’m Jeremy Shield, founder of Shield Contracting. I’ve spent the last two decades building trails, ski courses, and outdoor spaces that bring people closer to nature. While I’ve worked across three continents designing and constructing world-class ski and boarder cross courses for international competitions, my passion is increasingly rooted in creating sustainable, hand-crafted trails for hiking and biking.
There’s something incredibly rewarding about working with the land—reading its contours, understanding its stories, and shaping experiences that help people connect with wild places.
The Highlands Art & Tree Trail was a dream project for me. It brought together everything I care about: art, community, environmental stewardship, and world-class trailbuilding. I hope everyone who walks it feels the same inspiration I did while building it.
Start your project with Jeremy Shield: Shieldcontracting.ca
