Many people are surprised to learn that Pittsley isn’t a born and raised Minnesotan after skating in Edina since his second year of PeeWees and also because his Elite Prospects page lists Edina as his hometown, but he was born and raised in the suburb of Holly Springs, North Carolina, located just southwest of the state capital of Raleigh.

Obviously, there is hockey in North Carolina, but it’s certainly not the most popular sport in the area even though it has been gaining popularity over the past few years. Pittsley remembers becoming interested in the sport after scrolling through channels on the TV one day and finding a hockey game that was on. He started out as a big Sidney Crosby fan before eventually becoming a Carolina Hurricanes fan as well now as he has gotten older. He joined roller hockey at a young age and didn’t end up moving over to actual ice hockey until age five or six.

For squirt hockey and one year of PeeWees, Pittsley competed with the Carolina Jr. Hurricanes program, which pulled athletes from the entire state of North Carolina and sometimes required a 40/50 minute drive to practice since there weren’t many ice sheets in the area to practice on.

After seeing the passion that Pittsley had for the sport and the talent that he was starting to show as well, it seemed like a move out of the state was going to be inevitable. The Pittsley family wasn’t sure at first if Caleb should enroll in a prep school somewhere - which was the typical route for other skaters in the Carolinas - or if they should all move somewhere together. Caleb’s parents started to do some research on what could be the best fit for the family as whole and they soon found that Minnesota was a top candidate, especially with some family ties to the area since Caleb’s mother is originally from nearby Steven’s Point, Wisconsin, but his father is originally from New York.

After deciding on Minnesota, the next step was thinking more specifically about which area to move to. In 2016, which was around the time that they were going to move, Edina High School had won the Class AA state high school championship, which obviously made a positive impression on the Pittsley family, so after deciding between Edina and Prior Lake, they settled on Edina. It wound up being a fairly easy change for the three since Caleb would end up having many more on-ice opportunities within the Hornets hockey association and his parents wouldn’t have to do too much job-wise for the change either.

Deciding on Edina payed off immensely as Pittsley won the PeeWee AA state championship with the Hornets in his very first year with the Edina Youth Hockey Organization. He then won the Bantam AA state championship once as well before eventually suiting up for the varsity team at Edina.

Even though some might not think of hockey in Carolina as that popular or competitive compared to other states, it obviously prepared Pittsley quite well since he has had quite the success in Minnesota in the years following his family’s move.

In his first official season of varsity hockey for the Hornets in 2023-24, there was definitely a lot to get used to but Pittsley was able to learn a lot from a talented core of senior leadership and a very deep, exciting Edina squad as a whole.

“I feel like I struggled a lot at the start (of the varsity season), it was a lot faster paced and a different game and honestly everyone was a lot bigger and faster than me,” he said about making the transition up to high school hockey. “It was pretty shocking to me and hard for me starting out but as the season went on I feel like I got a lot better and my line got a lot better and we just really excelled and it was a really fun year.”

Edina was a top team that season, filled with guys who are now Division I committed athletes and/or leaders on their junior hockey teams.

“It was really good to learn from seniors like Jackson (Nevers - who is committed to Minnesota), Bobby (Cowan - who is now a freshman at Western Michigan), (Ben) Dexheimer (who is committed to UMass), and other players like that, they were very supportive and helped us through it and made sure that we were getting better and becoming the best that we could be as a team so I feel like that really helped me a lot,” he added.

The Hornets had only lost four games heading into the Minnesota Class AA state tournament that season, so it’s safe to say that Edina was a top team in the state. At state, the Hornets won their quarterfinal and semifinal matchups by scores of 6-2 and 5-2, so the team was rolling, and Pittsley earned three assists throughout those first two games. The state championship match was a different story though as the Hornets had to play a tough Chanhassen team and Edina was down by a score of 1-0 heading into the third period.

"After the second period, (Head Coach Curt) Giles came in the locker room and was telling us to stick with our game and that we’ll be fine and to just have the confidence that we can come back and win this game, and that’s what our team did,” said Pittsley about heading back out for the third period to try and win the state title in 2024.

“We just stuck around and eventually found one (a goal), and then we got a powerplay and Bobby (Cowan) obviously scored to win state. It was super surreal and super fun to just be out there in front of all those people playing for something that a lot of kids dream of when they’re young and to be someplace where a lot of kids want to be,” he added.

As a sophomore, Pittsley earned a respectable 18 points (5 goals, 13 assists) through 31 games played but he really started to make a big impact the next season as a junior. A big part of his improvements in the offseason between sophomore and junior year came due to having a knee surgery that drastically improved his skating with his left leg, which he feels like was definitely not at 100% throughout his first varsity season.

During his junior year, Pittsley played a much larger role within the forward-core of the Hornet squad since there were a lot of key seniors who graduated in the offseason prior. Between his improved skating and his larger role on the team, the forward from Holly Springs was able to rack up 43 points through 30 games in 2024-25 for Edina. That was fifth in overall point scoring for the team and second-overall in goals scored (21).

It was a little bit more of an up and down season for the Hornets in Pittsley’s junior season but the team was still ranked in Class AA and would eventually make another berth to the Minnesota state tournament.

“I feel like the season started out a little rocky and was a little rocky all the way to the middle of the year,” he said about his Edina squad. “Every year, Coach Giles always finds a way to lead us to have success so I feel like just listening to him and really bearing down in practice and putting in a lot of time and effort and working hard got us to where we wanted to be.”

In Edina’s state quarterfinal match-up, the Hornets had to face a tough Rogers team. The game wound up going to overtime tied at 1-1 and who else would score the game-winning goal other than Pittsley himself.

“I remember getting the puck and coming into the zone and I just wanted to get it on net because anything can happen, but I was super tired and I feel like all of us were super tired,” he said about the moment he scored the game-winner. “I didn’t really know I scored at first because the guy that was in front of me kind of screened the goal so I couldn’t really see the net. Everyone just stood up then and the lights went off and that was just a surreal moment for me and then celebrating with my teammates and being so glad that the game was done and that we were moving on, that was honestly the best feeling ever.”

Unfortunately, the Hornets would fall in a narrow 4-3 loss to eventual state champion Moorhead in the semifinal match but the squad would rebound to defeat St. Thomas Academy, 4-3, in the Class AA third-place game.

During his junior season, Pittsley started to become more of a recruiting target of various Division I college hockey programs due to his offensive explosion at Edina in 2024-25. Eventually, he wound up committing to Augustana in September of 2025.

“I just found the one (the college program) that I really wanted to go to and really liked. I really liked the head coach, which was pretty much the main thing for me, and they have a great stadium and a great fan base,” he said about why he decided to choose the Vikings, who are still newcomers to the Division I college hockey scene. He said that it’ll be fun to play with some of the other recruits in the future that he knows now a little bit, such as Minnesotans Cade Sherman (Rosemount), Brock Cheslock (Rogers) and his current Madison Capitols teammate Tyden Bergeson (Moorhead).

As for now, Pittsley is currently skating in Madison of the USHL and has four points through nine games played so far. He is still undecided on whether or not he will return to Edina for his senior season of high school hockey but is currently leaning towards staying in Madison.

“I think the first couple of games have gone well, I feel like I’m playing pretty well and showing my skills. It’s been super fun and it’s been a really great experience so far,” he said about his time with the Capitols this fall. It has helped that there are a lot of other Minnesotans on the team that can help him make the adjustment to juniors too, such as former Edina captain Jackson Nevers who is now captain of the Madison team.

“I think people can expect us to make a deep run in the playoffs, I think we’re really good,” he said about the Capitols squad in 2025-26. “We have a lot of young forwards but an older, more experienced, ‘D’ class this year so you can expect great shutdown defense and then as the season goes along I feel like the forwards will start getting better and better and we’ll just become a more complete team, which will be perfect for the start of playoffs.”

Pittsley has been impressive on the ice for Madison early on and even recently earned a call-up to the National Team Development Program, where he competed in a game against the University of Wisconsin, and he was also named a watchlist prospect in the NHL Central Scouting Preliminary List that was recently released in October of 2025.

“It was pretty surreal to find out from my coaches that I was playing in that game (with the NTDP), I honestly wasn’t expecting anything like that going into the coach’s office,” he joked.

So for now, Pittsley will be skating in Madison for the forseeable future and will be working on his game before eventually heading to Augustana for college. He likes to describe his playing style as being a lockdown centerman, a guy who can play defense first, can win a lot of puck battles while being successful in tight and in corners, and can obviously make plays and score goals too.

It seems like the move all those years ago from North Carolina to Minnesota has now officially payed off. Who knows now where Pittsley’s career will take him next?