The Highlands Sky 40 Mile Trail Run, held on June 20, 2026, in Davis, WV, is an iconic point-to-point ultramarathon renowned as the "Mountain State's crown jewel" for good reason. Hosted by the West Virginia Mountain Trail Runners, this challenging race carves a 40-mile (often closer to 41+ miles by GPS) path through the rugged and beautiful Monongahela National Forest, encompassing the Roaring Plains and the unique Dolly Sods Wilderness Areas. Runners will experience a diverse course, with roughly 75% technical trail, 15% dirt Forest Service roads, and 10% paved sections, navigating over 5,400 feet of elevation gain and nearly 4,900 feet of descent through a landscape that remarkably blends tropical and high-alpine environments.

The course is a relentless test of endurance, featuring significant climbs, boulder fields, rooted single track, and stream crossings where your feet are sure to get wet. Notable sections include a 2,000-foot ascent in the first nine miles and the infamous "Boar's Nest Trail," a mile-long, 1,000-foot rocky and rooty descent. Prepare for stunning 360-degree panoramic views from the Roaring Plains, which sit above 4,500 feet, and the peculiar, windswept heath barrens of Dolly Sods, reminiscent of Canadian forests. Midway through, runners will traverse the unique 7.5-mile gravel "Road Across the Sky." Typical race day conditions in late June bring highs around 73°F and lows near 54°F, with a 25% chance of precipitation, adding to the unpredictable mountain challenge.

Known as a "40 miler that feels like a 50," Highlands Sky has earned a reputation for its exceptional organization and enthusiastic volunteers. Eight aid stations are strategically placed along the course, offering a wide array of ultra-cuisine, though runners must carry their own liquid receptacles as the race is cupless. The event fosters a strong sense of camaraderie, culminating in a lively finish line at the Canaan Valley State Park Resort, which also serves as race headquarters and the shuttle departure point to the Red Creek start line. With a 12-hour cutoff and limited entries that sell out quickly on Groundhog Day, the Highlands Sky 40 Mile Trail Run is a bucket-list race for those seeking a true wilderness ultra experience in West Virginia.