Dillon Osleger is a geologist, conservationist, and trail builder whose debut book, Trail Work: Restoring the Paths and Stories of America’s Public Lands (Heyday, 2026), argues that trails are not neutral infrastructure but agreements between people and places, and that neglecting those agreements erases far more than footpaths. In this conversation, Osleger traces how each era’s economic priorities get redrawn into the landscape, from the Gold Rush to the Sagebrush Rebellion, and how that process is accelerating as campgrounds, visitor centers, and land management offices disappear from federal databases. He examines the Appalachian Trail’s drift from Benton MacKaye’s 1921 vision of rural community connection toward a culture of speed and personal achievement, and how the Forest Service’s aging volunteer base reflects a broader failure to treat stewardship as civic infrastructure. Osleger’s argument is ultimately a civic one: trail work is one of the few remaining spaces where people from genuinely different backgrounds work side by side for the same reasons, and that common ground is at risk.

The land itself is a kind of map, one that records what came before and what we choose to preserve.

Dillon Osleger is a geologist, conservationist, and trail builder whose debut book, Trail Work: Restoring the Paths and Stories of America’s Public Lands, reads as both a love letter and a reckoning. Named after Dillon, Montana, and raised by field geologists who hauled him on their excursions through the Canadian Rockies and the rangelands of southwestern Montana, Osleger grew up learning that the land itself is a kind of map, one that records what came before and what we choose to preserve. This episode continues The Wild Idea’s month of stewardship with a wide-ranging conversation about trails, history, and what the act of maintenance actually means.

One of the book’s central arguments is that trails are not neutral infrastructure; they are agreements between people and places. Like a palimpsest, the old document scraped and rewritten until its original text is nearly invisible, those agreements can be overwritten or simply forgotten. Osleger traces how each era’s priorities, from the Gold Rush to the Forest Service’s timber era to the Sagebrush Rebellion, show up in how the same landscapes were mapped and used. Today, he argues, the map is being redrawn again: campgrounds and visitor centers disappearing from federal databases, land management offices closing, scientists and stewards being erased from institutional memory. When a place disappears from the map, he says, it disappears from the questions kids ask.

The conversation moves through the Appalachian Trail and Pacific Crest Trail as case studies in how long-distance trails have drifted from their original purposes, which were economically and socially rooted in rural communities, toward a culture of speed and personal achievement that has little relationship to the land itself. It returns, finally, to the people who maintain the trails: the campground hosts, trail crews, and seasonal rangers who rarely receive the recognition the work deserves. Osleger’s argument is not nostalgic. It is a civic one. Stewardship, he says, is one of the few remaining spaces where people from genuinely different backgrounds can work side by side, swinging tools for the same reasons. The question the episode leaves open is how long that common ground can hold if we stop funding the people who tend it. 

In this episode:

• Trails as agreements between people and places — Osleger’s central argument: trails begin as relationships shaped by need and awe, and become contested when use changes faster than the original agreement can absorb.
• Maps as reflections of power — From the Gold Rush to the Sagebrush Rebellion, each era’s economic priorities get drawn into the landscape. Osleger traces how erasing places from maps erodes public faith in public lands, which in turn weakens the political will to fund them.
• The Unicoi Turnpike and the erasure of Cherokee history — Bill Hodge recounts one of the oldest continuously used travel paths in North America, a corridor that linked Cherokee Overhill towns in Tennessee to settlements in the Carolinas, and that served as the beginning of the Trail of Tears in 1838. Later, Forest Service trail work altered the path and erased irreplaceable Cherokee history in the process.
• The Appalachian Trail’s original purpose — Benton MacKaye’s 1921 vision connected the trail to rural economic life and community. Myron Avery’s volunteer corps built it into a physical reality through the 1930s. Osleger explores how the trail’s cultural meaning has shifted away from those community roots.
• How long-distance trail culture has changed — Osleger, who lives along the Pacific Crest Trail in Truckee, California, describes what has been lost as trails became venues for performance rather than connectors of people and place.
• The aging volunteer stewardship base — The Forest Service’s volunteer population is aging out, and fewer people are entering trail work at the community level. Osleger connects this to broader economic pressures that make stewardship feel like a luxury rather than a civic right.
• Awe as a bridge across time — Osleger’s most personal argument: public lands give us one of the few spaces where we can stand where thousands of people stood before us and feel connected to a longer arc of history. Awe, he says, is both deeply individual and genuinely connective.
• Celebrating the unsung workers — A case for recognizing campground hosts, trail crews, and seasonal rangers with the same respect given highway workers and rural nurses. These are public servants maintaining public goods that belong to everyone.

Links & Resources

Connect with Dillon:

• Website
• High Country News author page
• Instagram

Media & Books:

• Trail Work: Restoring the Paths and Stories of America’s Public Lands by Dillon Osleger (Heyday, 2026) — Osleger’s debut book, excavating the buried histories beneath America’s trails and making the case for trails as civic infrastructure. 
• Tangled Roots: The Appalachian Trail and American Environmental Politics by Sarah Mittlefehldt — History of the Appalachian Trail’s creation and the community involvement that shaped it; recommended by Bill Hodge during the conversation. 
• The Unsettling of America: Culture and Agriculture by Wendell Berry — Referenced by Osleger as a foundational influence on his thinking about land, culture, and the consequences of severing people from place. 

Organizations & Initiatives:

• NOLS (National Outdoor Leadership School) — Wilderness education program that Osleger attended at age 15 in the Sawtooth Mountains of Idaho; he credits it as a formative experience that confirmed his relationship with the outdoors. 
• Friends of the Forest Service — Nonpartisan network founded by Meryl Harrell that supports the U.S. Forest Service’s multiple-use mission; Harrell is a guest in the following episode. 
• American Rivers — National river conservation organization; Lisa Ronald, Western Montana Associate Conservation Director, appears in the following episode. 
• Wild and Scenic Rivers Coalition — National alliance of more than 50 river friends groups working to support wild and scenic river stewardship and advocacy; co-founded by Lisa Ronald. 

Places & Landscapes:

• Appalachian Trail — The 2,190-mile footpath from Georgia to Maine; discussed in terms of its original community and economic purpose and how that purpose has shifted over time. 
• Pacific Crest Trail — The 2,650-mile trail from Mexico to Canada, running through Truckee, California, where Osleger lives; used as an example of how long-distance trail culture has changed. 
• Sawtooth Mountains, Idaho — Location of Osleger’s NOLS course at age 15; part of the Sawtooth National Recreation Area in central Idaho. 

Government & Policy:

• Wild and Scenic Rivers Act (1968) — Federal law establishing the National Wild and Scenic Rivers System, protecting free-flowing rivers and their outstanding remarkable values from development; inspired directly by the fight to preserve the Middle Fork of the Flathead.
• Wild and Scenic designation of the Three Forks of the Flathead (1976) — The formal congressional designation that protected the North, Middle, and South forks; the 50th anniversary of this designation is being celebrated in 2026.
• Comprehensive River Management Plan — The congressionally mandated planning document governing management of the Wild and Scenic river system; the Flathead’s plan dates to the 1980s and a long-overdue update is expected imminently.

People Mentioned:

• Wendell Berry — Farmer, poet, and essayist; referenced by Osleger for The Unsettling of America and his foundational writing on the relationship between people, land, and culture.
• Benton MacKaye — Forester who conceived the Appalachian Trail in 1921, envisioning it as a corridor connecting rural communities and providing economic opportunity for those traversing it.
• Myron Avery — First chair of the Appalachian Trail Conservancy who organized volunteer crews to build the trail through the 1930s; his approach emphasized construction over MacKaye’s broader social vision, and the two famously fell out over that difference.
• Gifford Pinchot — First chief of the U.S. Forest Service; cited by Osleger as one of the historic public lands figures whose legacy risks being erased from institutional memory.
• John Muir — Naturalist and co-founder of the Sierra Club; mentioned alongside Pinchot as a foundational figure in American conservation whose name and legacy deserve to be passed forward.
• John C. Fremont — U.S. Army explorer whose 1842 Sierra Nevada expedition map is cited by Osleger as a document that records the landscape while simultaneously erasing the Washoe knowledge that made the route navigable. Osleger has spent time with Washoe historians who trace the overlap between Fremont’s “novel route” and the path the Washoe used seasonally for generations.
• Rachel Carson — Author of Silent Spring; referenced in the context of how neglect accumulates quietly until the damage becomes too visible to ignore.

Dillon Osleger is a scientist, writer, and environmental advocate whose work is anchored in society’s relationship with wild and rapidly changing environments. With an academic background in geology, ecology, and climate science, he has spent over a decade working on trail restoration, land management, and public lands policy across the American West. His writing has appeared in Outside, High Country News, the Los Angeles Times, Patagonia’s The Cleanest Line, and Earth and Planetary Science Letters, focusing on the confluence of land use, climate, environmental justice, and historical memory. Whether in Washington, D.C., or the backcountry of the Sierra, Osleger brings a grounded perspective to how people move through and care for place.

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