In 2015, Sam Brakeley stood at a crossroads in his life. His long-time girlfriend was moving to Utah, with or without him, and he was torn between following her or remaining in New England with family, friends, and the land he loved. So he set out to complete the Catamount Trail, a 330-mile cross-country ski trail that runs across Vermont from the Massachusetts border to Canada. He took advantage of his time in the woods to reach a decision—and brought Henry Knox along for the trip. In 1775, Knox undertook a winter journey of similar length, retrieving dozens of artillery pieces from the recently captured Fort Ticonderoga on Lake Champlain and dragging them 300 miles through snow and cold to Cambridge, Massachusetts, to help George Washington drive the entrenched British army from Boston. Knox, too, faced his own challenges in love, leaving behind a young pregnant wife. By exploring Knox’s eighteenth-century physical and emotional journey while undertaking his own twenty-first-century trip on the Catamount Trail, Brakeley reminds us that history has many lessons to offer the living.