OTIS — Whenever Tom Soules ran into Jack William O’Brien around town, he looked forward to hearing about the young outdoorsman's latest hunting trip and what he and his father, Mike, had brought home.

Jack O'Brien, 20, of Otis, died in a 2022 snowmobile crash in the western Adirondacks in New York state.

“I lived through that young man, it was great to run into him all the time,” said Soules, a fellow hunter and a member of American Veterans Post 77, a sponsor of the 5th annual Smile Like Jack Memorial Road Race.

Soules was among some 700 people who gathered outside the Knox Trail Inn for Saturday's race, a 5K, 10K and family fun run along Route 23 honoring O’Brien, an avid outdoorsman from Otis who died in a snowmobile crash on March 3, 2022, at age 20.

Mike O’Brien, the father of Jack William O’Brien, makes announcements to the growing crowd at the start of the fifth annual Smile Like Jack 5K/10K walk and run in Otis on Saturday.

Created by Jack’s parents, Mike and Star, along with other family members, the race is the Smile Like Jack Memorial Fund’s largest fundraiser. The fund supports Berkshire and Hampden County residents and organizations that reflect Jack’s values, including hard work in the trades and embracing the outdoors.

The memorial fund and race take their name from the smile Jack wore wherever he went — one that family and friends say reflected his generous spirit and love of life.

“He definitely had that smile,” said Soules. “He was a great young man, he really was.”

Around 700 participants begin the fifth annual Smile Like Jack 5K/10K walk and run in Otis to benefit the Smile Like Jack Memorial Fund; established in honor of Jack William O’Brien, who died in 2022 in a snowmobile crash at age 20.

Before his death, Jack started his own landscaping business, worked for his father's company, Saloomey Construction, and even built his own house shortly after graduating from Monument Mountain Regional High School — all while spending as much time outdoors as he could.

“He just gave to everyone and this would make him so happy, everyone coming together,” Jack’s sister, Erin, said before the race. “He always said, ‘you’re here for a good time, not a long time.’”

With race entry fees and raffle proceeds, Mike expected to raise about $100,000 for the fund this year, similar to the amount raised last year.

Carla Patterson, left, greets Star O’Brien, whose family established the Smile Like Jack Memorial Fund after O’Brien’s son, Jack William O’Brien, died in a snowmobile crash in 2022. Patterson, whose daughter died many years before, connected with O’Brien after her son’s crash, and the two were able to provide each other with emotional support after suffering the same loss, said Patterson.

Before participants filed through the inflatable start line, they could buy raffle tickets to try to win dozens of outdoorsy-themed prizes donated by sponsors that included Blueberry Hill Farm, Hairy Hoof Highlands from Coventry, Vt., East Otis Automotive and Williams Stone Co.

Individuals and businesses donated prizes ranging from a camping cooler stocked with White Claw beverages to paddleboards, an electric bicycle and a backpack leaf blower.

Otis firefighter Max Sulik was one of the first people to pass the finish line after running a timed 5k. It was his third year participating.

Participants pick raffle prizes to drop their names into at the start of the fifth annual Smile Like Jack 5K/10K walk and run in Otis to benefit the Smile Like Jack Memorial Fund.

“We have a great community here and this supports an amazing cause,” he said, still catching his breath from the run.

The event has continued to grow since its first year, when about 300 people participated.

“I never thought this is what it would turn into,” said Star. “Thank you to the community of Otis and beyond.”

Runners make their way to the finish line in the fifth annual Smile Like Jack 5K/10K walk and run in Otis to benefit the Smile Like Jack Memorial Fund; established in honor of Jack William O’Brien, who died in 2022 in a snowmobile crash at age 20.

A constant stream of well-wishers hug Star O’Brien, Jack William O’Brien’s mother, at the fifth annual Smile Like Jack Memorial 5K/10K race in Otis on Saturday.

The family has not finalized this year's recipients, but Mike said the fund's goal remains the same each year: "to get kids motivated and outdoors."

Last year, the fund awarded scholarships to students at Monument Mountain and Lee High School for college and trades education, and Muddy Brook Elementary School.

Other past donations include a scholarship for a young man’s taxidermy education, $1,000 to the Otis Fireworks Display, $1,000 to the Otis Ridge Ski Race Team and $1,000 to the Westfield High School Gymnastics Team for new equipment.

Around 700 participants begin the fifth annual Smile Like Jack 5K/10K walk and run in Otis to benefit the Smile Like Jack Memorial Fund; established in honor of Jack William O’Brien, who died in 2022 in a snowmobile crash at age 20.

Looking ahead, Mike said the organization is currently working through a lease agreement with the Izaak Walton Field on Route 8 in Otis. He and his family hope to take donations to rent it out for weddings, graduation parties and other outdoor events. They also envision using the space to host community activities like a fishing derby and license-to-carry courses.

“I think what they’re doing with the kids and scholarships, it’s wonderful,” said Becket resident Colleen Kelly-Cahill, who has participated since the first race with husband Sean. “It’s a great way to keep Jack alive.”