Smile Like Jack 10k

The Smile Like Jack 10k is part of the Smile Like Jack 5k/10k/Fun Run event held annually in East Otis, Massachusetts, at the Knox Trail Inn. Scheduled for July 12, 2025, the event features a competitive, chip-timed 10k race alongside a 5k and a family fun run/walk. Participants enjoy a lively atmosphere with food, beverages (including 21+ options), music, and raffles.

Early bib pickup is available the day before. The event honors the legacy of Jack William O’Brien, celebrating his passion for hard work and the outdoors. The race is rain or shine, with a T-shirt cutoff date of June 1. Visit the organization's website for the most recent information.