Our School

Holy Cross High School President, Dr. Thomas C. Pellegrino and Father Jim Sullivan from the Basilica of the Immaculate Conception united for a noble cause at Lake Waramaug in Warren, CT for the annual Our Fathers' Ride. This event, initiated by Fr. Jim in 2005, endeavors to raise funds and awareness for Catholic education. For him, this bike ride is a moment of reflection to decompress, rejuvenate and “empty his tank.” He thus believes that it is a way to challenge oneself, release inner potential, and contribute to society by giving back selflessly.

Fr. Jim recalls his mother telling him at age fourteen that she bicycled with her sister from Waterbury to Montreal at age seventeen. He figured that if his mother could do it, he would do it. That story was the genesis of a life-long love affair with long-distance bike riding. One of his first rides was to Providence College when he was nineteen. 

It was during his first assignment as a priest in Torrington in 2005 when Father Jim got the idea of doing an annual bike pilgrimage in support of Catholic education. “Ten priests rode with me to Maryland. The oldest was 63 years old. I was 55 at the time. The following year, Fr. Tony Smith joined me on a ride from Waterbury to Montreal.”

A few years into this annual pilgrimage, Fr. Sullivan wanted to make it more community-based. He wanted more to join him both on the bike trails and on the sidelines. “We decided to make this an all-day event in a local area so that more parishioners could join in.”

For the 2023 Our Fathers’ Ride, Dr. Pellegrino joined Fr. Sullivan . “I am not a cyclist.   If anything, I am a runner, but when Fr. Jim invited me to do this, my answer was simple - yes, of course.”  Dr. Pellegrino and Fr. Jim  started at 4:00am on June 21, the longest day of the year.  Dr. Pellegrino’s ride went 12 hours. “My original goal was 68 miles in honor of the year our school’s doors opened. I finished at 102 miles. It was definitely an “empty the tank” experience for me.  But the objects of our efforts - our schools - were clearly worth it” 

For Dr. Pellegrino, this was a time to reflect and give as so many others have for a cause close to his heart. “We were there so that we could raise funds to make Catholic education more accessible for students and families. The consistent story of private Catholic education is finding ways to make it affordable while still being able to pay our bills. I want to thank Fr. Jim as well as my riding partner, Greg Dean. Greg is a 1986 graduate of Sacred Heart High School. Greg and I  were laughing at how a Sacred Heart guy was helping aHoly Cross guy. The kidding asisde, we knew that we are all part of a bigger tent with a unified goal. It is imperative that we all support each other to keep Catholic education alive in the Greater Waterbury area.”  

“Holy Cross High School is the only Catholic high school in Waterbury,” said Fr. Jim. “We need to keep it going. It is a good school.” Fr. Jim recalled when he attended Holy Cross’s Oronoke After Hours event in the spring of 2023. He went thinking he wasn’t going to know anybody. He remembers being at the front door for twenty minutes before he got to the registration desk. “I was amazed at how many people I knew. Parishioner after parishioner came in.  It was a lot of fun.” 

This ride brought together two factions of the Waterbury Catholic community for a worthy purpose. Their individual efforts came together to support Catholic education, and the ride served as a reminder that as individuals, we can always do more, give more, and strive harder to reach our potential. Emptying oneself and giving to others is a virtuous act that unites society and makes the world a better place.