The Knox Trail Inn, East Otis MA
Saturday, July 11th, 2026
Event Overview
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!
Event Schedule
- Early Check-in: Friday 7/10/2026, from 4-7 PM at the Knox Trail Inn, for those who wish to get their bibs the evening before.
- Registration Time: Day of registration and check-in begins promptly at 7:00 AM.
- Race Kickoff: The race kickoff is at 9 AM.
Pricing
- Competitive Race: Chipped Timed 5k/10k - $40
- Family Fun Run/Walk: Not Timed - $35
We hope to see you there!
Important Dates
- T-shirt Cutoff: June 1st.
- Weather Policy: 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.
Learn More
For additional information on The Smile Like Jack Memorial Fund, and for live updates, please visit our website: https://smilelikejack.com
Registration Link
For more details and to register, please visit: Smile Like Jack Race Registration
Course Map
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