Masterson joined in the game, along with former big league pitcher Aaron Myette and Twins Minor Leaguer Kyle Gibson. They were all there working on a project with the "Mission of Mercy" -- an organization that Masterson will team with once again in early December for another trip to the Dominican.
It is a chance for Masterson, who was involved in enough charitable and community endeavors to earn a nomination for Major League Baseball's Roberto Clemente Award this past season, to help out with the organization's projects, but to also try to find ways to put smiles on some kids' faces.
That is why the stick ball game stands out so clearly in Masterson's mind.
"There was a huge tree behind second," Masterson said. "We each did a great job of sending towering shots over the tree. You know, there wasn't anything spiritual or overly educational. It was just so much fun, and random. And they enjoyed it just as much as we did."
This year, Masterson will return to Moca, Dominican Republic, with some friends for a week-long stay from Dec. 2-8. It will be an opportunity for the pitcher to see the progress made in the area since his last visit two years ago, when he and others helped with a handful of construction projects.
In his last visit, Masterson's group assisted Mission of Mercy with the building of a two-story building, a pavilion, a basketball court and a baseball field. Masterson -- a right-handed sinkerballer for Cleveland -- said he made sure the mound was "nice and high" on the diamond they helped create.
Once the field was completed, Masterson and Mission of Mercy held a dedication ceremony that included plenty of games for the children, as well as on-site medical examinations. Mark Pluimer, the president of Mission of Mercy, has been thrilled to have Masterson among those helping out with the group's efforts in the D.R.
"Justin has been a tremendous encouragement to the children of Moca, a poor, small, forgotten village outside of Santiago," Pluimer wrote in an e-mail. "The 'Field of Dreams' has pulled the whole community together."
The trips are not entirely labor-filled, though.
"A lot of the work is visiting the people," Masterson said, "hearing their stories, encouraging the workers who are there year round and telling them about Jesus Christ."
Masterson, who is the son of a pastor, is very open about his Christian faith and is involved with a mix of intiatives that reinforce that. Mission of Mercy's vision, according to its website, is "to see the children of developing nations, who live in poverty, experience transformation and wholeness through God's love."
The organization has projects in many countries on multiple continents. Masterson learned of the group through his agent, Randy Rowley, who thought it would be a nice idea for Masterson and others to help entertain some of the kids while the organization's medical team did its work in the Dominican Republic.
Masterson was immediately interested in volunteering his time.
"Just the opportunity to try and positively impact some lives is inspiration enough for me," Masterson said. "And I went to the Dominican in college and have had a love for the language and the people ever since."
Another aspect of Mission of Mercy's work is a program that allows people to sponsor children in various nations. Masterson and his wife, Meryl, do not currently sponsor a child, but they are hoping to do so in the future.
"Maybe we will base it on some of the kids that we meet this year," Masterson said. "Not all the kids we meet are able to be sponsored."
Masterson hopes to get more players involved in the program. One plan he has this year is to take a group of kids to a winter ball game in the Dominican, providing a chance for them to take in a game and to meet some other players.
"Most of these children have never been to a baseball game," Pluimer said. "When an MLB player like Justin spends time with these kids, it builds their self esteem. It gives them hope for the future. Justin and his wife, Meryl, are great with the kids. Their investment in the children brings hope -- and memories that last a lifetime."
Masterson hopes more players will join the efforts in the future.
"Hopefully next year we can get some more people involved," Masterson said. "I mean, it's people helping people. Who doesn't like that?"
After all, more players could make for an even better stick ball game.