Smile Like Jack 5k/10k/Fun Run

Lace up for a heartfelt journey at the 5th Annual Smile Like Jack 5k/10k/Fun Run on Saturday, July 11, 2026, in scenic East Otis, Massachusetts. This impactful event offers participants a choice of a 6.2-mile (10k) or 3.1-mile (5k) chipped-timed race, alongside a non-timed Family Fun Run/Walk, ensuring a distance for every ability. The race is more than just a competition; it's a vibrant community gathering held in memory of Jack William O'Brien, an avid outdoorsman whose infectious smile touched many.

Starting and finishing at The Knox Trail Inn, the Smile Like Jack race is a "rain or shine" event, embodying a resilient spirit. While specific course details regarding terrain and elevation are best confirmed on the official race website, its designation as a "Road Race" suggests a route winding through the charming East Otis area. Typical race day conditions in July offer pleasant running weather, with highs around 85°F and lows near 62°F, and a 17% chance of precipitation. Beyond the run, participants can look forward to a lively atmosphere complete with food, beverages (including 21+ options), exciting raffles, and music, all contributing to a day filled with smiling faces.

The Smile Like Jack Memorial Fund, established in 2022, channels proceeds from this event into supporting educational programs, particularly in trades, preserving the outdoorsman lifestyle, enhancing habitat, and engaging in community outreach, fulfilling Jack's legacy of living life to the fullest. This annual road race is a cornerstone fundraiser, celebrated for the invaluable outpouring of love and support from the local Otis community and beyond. Join fellow runners and walkers to contribute to a meaningful cause while enjoying a memorable race day experience.