4th Annual Smile Like Jack Road Race

By Riley Bailey

August 2025

On July 12th, 2025 the Smile Like Jack Memorial Fund hosted their 4th annual road race in honor of the beloved Jack William O’Brien. Jack, a lifelong resident of Otis, passed away tragically on March 3, 2022 in a snowmobile accident. At the time, he was just 20 years young. Jack’s family started the memorial fund in his honor to continue his legacy and provide others the opportunity to pursue their dreams in the trades, further their educations and support communities near and far.

Erin, Michael & Star O’Brien (Jack's sister, Dad & Mom). Photo: Suzy Avery

The Smile Like Jack road race has become a summer tradition for the Town of Otis. The event is held on the morning of the Otis Reservoir fireworks each year and the race kicks off a fun-filled weekend in our small town. This year the Smile Like Jack Memorial Fund had over 700 participants – the fund's biggest race yet.

The day kicked off at the Knox Trail Inn with check-in starting at 7 am. The mobile coffee truck, Best Damn Espresso and New England Dairy, set up to fuel racers & volunteers. The race began at 9am and runners began their 5k or 10k along the Otis Reservoir. As the racers started to cross the finish line, the Smile Like Jack Memorial Fund sold JWO merchandise and raffle tickets for the general bucket raffle. The raffle prizes ranged from beach bags, to paddle boards, to weedwackers. All of the prizes were donated by the Smile Like Jack supporters.

Runners and walkers on Route 23. Photo: Suzy Avery

At the end of the day, the community of Otis and many others from out of town showed up to support the O’Brien and Saloomey families. The race wrapped up at 12pm with an award ceremony and a toast to Jack and his best friend Caleb Carlson who passed away this past November. The bittersweet day was a success thanks to the numerous sponsors, donors, participants and volunteers. Next year will be the 5th annual Smile Like Jack 5k/10k. It’s hard to believe that it will be the 5th race in honor of Jack, but in the words of the O’Brien and Saloomey families, “with all of your love and support, it makes the pain of Jack’s loss a little bit more bearable.”

Runners, set your watches! Photo: Suzy Avery