When
Saturday, July 11th, 2026
Where
The Knox Trail Inn, East Otis MA
Distances
5K · 10K
About this race
Event Information
Join us Saturday, 7/11/2026 for our Fifth Annual Smile Like Jack Family Fun Run/Walk. We will have food, beverages (21+ options too), amazing raffles, music, and lots of smiling faces!
- Early Check-in: Friday 7/10/2026, from 4-7 PM at the Knox Trail Inn.
- Day of Registration: Begins promptly at 7:00 AM.
- Race Kickoff: Starts at 9 AM.
- URL: Race Information
Pricing
- Competitive Race: $40 (Chipped Timed) 5k/10k
- Family Fun Run/Walk: $35 (Not Timed)
- T-shirts Cutoff: June 1st.
- Event Status: This event is rain or shine!
Jack's Story
The Smile Like Jack Memorial Fund was established in memory of Jack William O’Brien, a loving son and brother, caring friend, and hard-working young man that touched the lives of many with his contagious smile. Jack tragically passed away in a snowmobile accident on March 3rd, 2022. In his 20 short years, he had accomplished many things and leaves behind a legacy that is in a caliber of its own. Jack lived life to the fullest. He was always working exceptionally hard to accomplish his set of goals while also living the outdoorsman lifestyle: fishing, hunting, and riding. Our goal is that the Smile Like Jack Memorial Fund will bring other individuals (with similar passions) the opportunity to live their legacy just as Jack would - working immensely hard in the trades and living life to the fullest in the great outdoors.
- Website: For additional information on the Smile Like Jack Memorial Fund, please visit our website: https://smilelikejack.com
Course map
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