Chequamegon National Forest Pine Line Trail

Following the abandoned Soo Line Railroad bed, this 24-mile trail stretches from Medford to the Mondeaux Flowage through terrain that changes every few miles. The old railroad bridges are gone, replaced by muddy creek crossings that’ll cake your rig in Wisconsin clay. Around mile 16, you’ll hit the infamous Bog Hollow section where the trail disappears into knee-deep muck during wet seasons — locals call it the ‘truck eater.’ The payoff comes at Mondeaux Dam, where bass fishing and swimming holes await.

Easy to moderate depending on conditions, but that bog section will humble a stock truck fast. High clearance essential, 4WD recommended for wet conditions. Avoid April through June unless you enjoy winching. Best from July through October when the trail firms up. No permits, but check the flowage water levels before heading out. Plenty of dispersed camping along the old rail right-of-way, and the fishing at Mondeaux makes the muddy approach worthwhile. Bring recovery gear and expect to use it.