Caleb Freeman was an average runner for most of his middle school career and contemplated giving up the sport all together when he entered his freshman year at Haddam-Killingworth. However, Caleb stuck with it and worked hard to become a top-notch runner with the Cougars’ boys’ cross country, indoor track, and outdoor track teams.

Caleb is entering his senior year at H-K and will serve as one of captains for the cross country squad this fall. Caleb has helped the Cougars win the Shoreline Conference title in each his first three years with the team, earning All-Conference honors for all three seasons.

“I have been running cross country since 5th grade, but was bad at it all of middle school, and I didn’t really get into running until I joined the high school cross country team my freshman year,” says Caleb. “My brother [Seth] convinced me to join the team in high school as I was not going to, but helped me get into it, and the team culture and kids made me start to enjoy it.”

Following a successful cross country debut at H-K, Caleb joined the boys’ indoor track team and helped the Cougars claim the Shoreline Conference crown in both his freshman and sophomore seasons. This spring, Caleb signed up for the outdoor team and made huge contributions toward H-K’s run to winning both a Shoreline Conference title and Class M state championship, competing for a 4x800 relay that finished first at Shorelines and placed second in states.

The relationships that Caleb created with his colleagues on all three teams played a big part in his decision to keep running. As he formed strong bonds with his fellow Cougars, Caleb continued to improve his times in all of his events.

“My favorite aspect of the sport is how close the team is. It is almost like a family that always supports you, but at the same time, when you race, it’s just you,” Caleb says. “You have nobody else to rely on. It’s you—how much work you put in before, how well you prepared, the long runs and workouts, and how much you are willing to give.”

Caleb credits his older brother Seth, a 2019 H-K graduate, for pushing him to become an elite runner. Caleb will always cherish the experience of competing alongside his brother as a freshman with the cross country team. Caleb actually finished ahead of Seth when the Cougars raced at states that year.

“My favorite moment was at states my freshman year. My older brother was a senior and captain of the team at that point and, after he got me into running and convinced me to join the team, he was my role model on the team and the runner I wanted to become,” says Caleb. “I ended up beating him that race and, instead of being jealous or mad, he found me at the finish, gave me a hug, and congratulated me. Everything he did for me, he set an example for the runner I wanted to become.”

Caleb’s personal-best time for a cross country 5K is 16 minutes and 40 seconds. For track, Caleb’s top time in the 1,600 is a 4:39, and his personal best in the 3,200 is a 9:59. As he gets ready to begin his senior year, Caleb is ready to turn in his best season yet on the cross country pathways.

“I feel very confident going into this season,” Caleb says. “Summer training with the team was very good, and I feel strong and ready to race for our first meet on [Saturday] Sept. 11. I have big goals for this season.”

Matt Diglio, who is Caleb’s head coach for both track and cross country, was impressed with how Caleb burst on to the scene as a freshman and promptly became one of the Cougars’ varsity runners. Diglio has seen Caleb continually get better since then, and he has high expectations for what Caleb can achieve during his senior year.

“Caleb has improved as a runner and has gained more confidence in himself and his abilities over the years. He has had the benefit of having great leaders and training partners during his earlier years, but this fall season, he will be counted on to be not only our top runner, but also a leader and captain of the team,” says Diglio. “Caleb is a hard worker and dedicated to the sport, and I am excited to see what he can accomplish this fall and for his senior track seasons.”

Caleb’s relationship with Diglio quickly transformed from a player-coach bond into a friendship. Caleb says that he can go to Diglio with any issue that comes up.

“My relationship with my head coach is great. He has helped me and taught me a lot, both about running and everything else,” says Caleb. “I wouldn’t be the runner or person I am without him. I’m able to go to him with any problem I have.”

There were no State Championship meets for cross country last year as the CIAC held an abbreviated season due to COVID-19. The CIAC is slated to hold state meets this fall, but with the pandemic still persisting, Caleb is taking every practice one day at a time and won’t take any race for granted. In the end, Caleb wants to help H-K put together another successful season like the club did in 2020.

“I was very worried about going into cross country last year. The season did turn out to be weird. We had fewer races than usual, and they were all smaller races against fewer teams,” Caleb says. “Once I started to race, though, I realized I was in good shape and was doing well and lost all my worry.”