Our Mission

Recent NEWS

On February 7, 2023 Smile Like Jack awarded a scholarship to a student in Canaan, CT towards his Porter & Chester Technical School tuition.


Community Outreach

1st annual Smile Like Jack Memorial Road Race 2022

The first annual Smile Like Jack Memorial Race was nothing short of amazing. The outpouring love we received 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: Candy Chaffee, Tanya O’Brien, Star and Mike’s nieces: Darby and Keelin Bailey, Derek Poirier from the Highway Department, Lori Curtin, Karen Amanti, Berkshire Running Center, 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 showed up for the O’Brien family on July 9.

Again, we have no words to express our gratitude.



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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