Greenfield native Sam Calagione has accomplished a lot in his life. But on Friday, the founder of Dogfish Head Brewery will get to live out a dream he’s had since he was a child. 

Calagione will throw out the first pitch at Fenway Park before the Boston Red Sox game against the Chicago White Sox. The game is scheduled for 7:10 p.m. with the ceremonial first pitch slated to take place minutes before. 

It’s the opportunity of a lifetime for the 55-year-old who grew up playing his youth baseball in Greenfield, competing with the Knights of Columbus’ GMLB squad. 

“It’s beyond my wildest dreams,” Calagione said. “It’s extremely poignant to me. Some of the earliest memories are of my dad, my grandfather and I going into Boston for Bruins games and Red Sox games. One of my earliest memories is being at a Red Sox game and my grandfather telling me about how he saw Ty Cobb play and slide into second [base] here at Fenway.”

How did Calagione wind up in this spot? Friday night is Fenway Park’s annual Grateful Dead Night. Calagione, whose love for music started from scanning the radio in Greenfield and listening to WRSI as well as college radio stations at Hampshire College and UMass, has been involved in many brewery collaborations with musicians, from Pearl Jam to Deltron 3030 to The Flaming Lips. Calagione says his company’s most enduring and robust collaborations has been with the Grateful Dead, however. 

On the strength of a great relationship with members of the Grateful Dead, as well as it being milestone years for both the Grateful Dead and Dogfish Head, the brewery — which was bought by and merged with Boston Beer Company in 2019 — released its “Grateful Dead Juicy Pale Ale” earlier this year in collaboration with the band. It has been a successful launch for the company. 

“I built Dogfish Head using the benchmarks of seeing how indie rock and hip hop took off,” Calagione said. “Music was always an inspiration for our brand. I’ve become good friends with their basest Phil Lesh and his sons, but mostly lately with David Lemieux who is the Grateful Dead’s archivist and historian. This year is the Grateful Dead’s 60th anniversary, it’s the 30th anniversary of Dogfish, it’s our 10th anniversary of Dogfish being the official brewery of Record Store Day. We figured let’s blow it up and make it the biggest beer release of the year. Now it’s turned into the fastest growing beer at Dogfish since we launched our 60 Minute IPA almost a quarter century ago. Year to date this year the Grateful Dead Dogfish beer is the No. 1 new innovation in all of craft beer nationally which is really exciting for our brand.”

Calagione — who now resides in Delaware where Dogfish Head Brewery is headquartered — was already planning to be at Fenway on Friday for Grateful Dead Night. When Lemieux heard he’d be in attendance, he told him to get in touch with the Rex Foundation, a charitable organization created by “Members of the Grateful Dead and Friends.” 

Once he got in touch, they worked it out to get the Greenfield native to throw out the first pitch. 

“We’re doing this Fenway celebration in partnership with the Rex Foundation which is a wonderful non-profit in the Grateful Dead universe which is focused on education, environmental and community building,” Calagione said. “We got along great with the Rex Foundation folks and away we went with this amazing opportunity to take the mound on Friday.”

Calagione attended Northfield Mount Hermon School during his high school years, and his children also went on to attend NMH. He credits the school for helping shape him into the person he is, and helping him develop the skills to build Dogfish alongside his wife, Mariah. 

One of those skills goes back to creativity, where Calagione said he sees a connection between his company and the Grateful Dead, making the partnership all the more meaningful. 

“Harking it back to what I learned at Northfield Mount Hermon, even though I got kicked out of school in March of my senior year, it’s still where I became who I am today, especially as an entrepreneur,” Calagione said. “Northfield Mount Hermon’s rally cry is they educate the head, the heart and the hand. The head's easy — that's academia. Every grade school does that, but the heart is about giving back to your community, using your knowledge and your education and your skills to give back to your community. The hand is all about the creativity and the work ethic. When you look at the Grateful Dead, all these different musicians, Phil Lesh was a classically trained jazz musician. Jerry Garcia was bluegrass, Phil Lesh was straightforward rock and roll but they came together and made this sort of unique, awesome rock and roll transformer that was so epic and enduring that 60 years later, a 26-year-old could be digging the music just as much as a 50-year-old.”

Calagione still holds ties to his alma mater. He and his wife — who he met at NMH — will be the keynote speakers at Northfield Mount Hermon’s 142nd commencement ceremony on May 25.

“My wife, Mariah, deserves the bulk of the credit for our ongoing engagement with the school, in terms of the hours that she put in every week as the chair of the school, along with our fantastic Head of School, Brian Hargrove,” Calagione said. “It's a really unique opportunity for us, because this is the first time this school has ever done a joint commencement speech by a couple that went there and a couple who worked side by side for over 30 years. We haven't written our talk yet. Don't tell Brian Hargrove that, but we're going to, we're going to do that as we drive down from Fenway on Saturday.

“Coming back to a community that mattered to our heart, and being in a position to give back to that community that we love so much and that our kids love so much going there has been really, really rewarding for us,” he added. 

Calagione will be surrounded by friends and family, including his parents, at Fenway on Friday. Friends from NMH will also be attendance.

As friends do, they’ve spent the last week sending him videos of celebrities failing at their first pitch like the infamous throws from 50 Cent to Mariah Carey, letting him know they’ll never let him live it down if his pitch ends up bouncing 10 feet in front of home plate. 

He’s gone down with a neighbor in Delaware to a local school to practice the pitch, and he plans on throwing from the mound. 

“The existential question for those fortunate enough to get to do this is whether to throw from in front of the mound, which is safer, or go up on the big hill and go for it,” Calagione said. “Right now, I’m hoping to have a little liquid courage with our Grateful Dead beer and step up to the mound and throw one with my big boy pants on.”

Looking for the Grateful Dead Juicy Pale Ale yourself? Visit www.dogfish.com/brewery/fishfinder to find which local stores carry the brew.