On October 28, 2024, Caleb Snow interviewed Isaac Vaccaro for an oral history project on Blue Hill Mountain. Vaccaro, a math teacher and cross-country coach at George Stevens Academy, shares his experiences as a dedicated runner on Blue Hill Mountain, which he considers both a personal challenge and a source of community connection. Since moving to Blue Hill, Vaccaro has run the mountain over 460 times, often in challenging conditions, including winter ice and early-morning darkness. He describes how the mountain’s physical demands have enhanced his discipline, resilience, and mental toughness, values he instills in his students and athletes. Vaccaro discusses his role in the annual Blue Hill Mountain Trail Fest, where he helps maintain trails, selects race routes, and promotes local engagement with the mountain. He reflects on the importance of stewardship, explaining his commitment to trail upkeep despite his admitted enjoyment of occasional off-trail adventures, which sometimes conflict with conservation efforts. Vaccaro also recounts memorable experiences, such as running alongside a parasailer and completing endurance feats, including the grueling Camden Hills 50K. His narrative emphasizes the balance of respect and challenge that Blue Hill Mountain offers, fostering a profound sense of place and community.