Our Mission
Founded in 2022, The Smile Like Jack Memorial Fund is a nonprofit organization that was established to honor the legacy of an avid outdoorsman, Jack William O’Brien. The Smile Like Jack Memorial Fund’s mission is to raise funds in support of the preservation of the outdoorsman lifestyle, educational programs, habitat enhancement, and community outreach.
Recent NEWS
April 2025, The Smile Like Jack Memorial Fund, in partnership with Whitetails Unlimited, stocked the Otis Reservoir with 500+ Rainbow Trout. Thank you ALL for your support as you have helped make this donation possible by your endless generosity.
2023-2025 Donations & Grants
Annual Smile Like Jack Memorial Road Race
The annual Smile Like Jack Memorial Race is our biggest event of the year. The outpouring love we receive from our small community of Otis, friends, and family (those near and far) is invaluable.The O’Brien family thanks you. This has not been easy, however the support from all of you has been of great comfort.
THANK YOU to: Star and Mike’s nieces, Riley Bailey, Darby Stewart and Keelin O'Rourke, Derek Poirier from the Highway Department, Lori Curtin, Karen Amanti, Fast Track Timing, The Knox Trail Inn, The Otis Fire Department, The Otis Police Department, The Town of Otis, every single sponsor, everyone who donated a prize for the raffle, all of our volunteers, and every person who shows up for the O’Brien family on race day.
Again, we have no words to express our gratitude.
Sign up for our July 12th, 2025 Road Race
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Donate to Smile Like Jack
By donating to the Smile Like Jack Fund you’re helping to raise funds in support of the preservation of the outdoorsman lifestyle, educational programs, habitat enhancement, and community outreach.
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