Smile Like Jack 5k/10k/Fun Run 2026

The Smile Like Jack Memorial Race begins and ends at the Knox Trail Inn in East Otis, Massachusetts, within the small community of Otis. This yearly July event offers chip-timed 5k and 10k races, alongside an untimed Family Fun Run/Walk for those seeking a more relaxed, noncompetitive choice. The race serves as the primary fundraiser for the Smile Like Jack Memorial Fund, established in 2022 to honor Jack William O’Brien, who enjoyed fishing, hunting, riding, and outdoor activities. Race day features food, a broad beverage selection, raffles, and music. The fund contributes to outdoor education, habitat restoration, community outreach, and initiatives like stocking Otis Reservoir with over 500 rainbow trout.