Brian Ditchfield, artistic director of the Martha’s Vineyard Film Festival, had a question the day following the 2016 presidential election: “Are we as a country really as divided as we may perceive ourselves to be?”

“I was contemplating the apparent divide in the country that we’ve been told about over and over again — about the ‘coastal elites’ versus the midwest, rural versus urban,” Mr. Ditchfield explained. “We’re put into all of these categories in the news media and I was wondering if there really was that disconnect.”

In an effort to answer this question, Mr. Ditchfield came up with an idea: take a group of Vineyard students on a filmmaking trip to different parts of the United States, an expedition that would ultimately lead a group of five West Tisbury School students to Chicago, Ill. and Louisville, Ky. during a one-week documentary roadtrip.

The hopes for the trip? To hone their interviewing and filmmaking skills, to explore cities and towns miles away from the familiarity of the Island, and to discover an answer to Mr. Ditchfield’s question.

Seventh-graders Annabelle Brothers, Jack Lionette, Mya O’Neill, Tobey Roberts and Emma Williamson were selected to participate in the trip accompanied by Mr. Ditchfield and filmmaker Danielle Mulcahy. Funded by a grant from an anonymous donor, the group left the Island on June 2, cameras in tow, and headed for Logan airport where they flew to Chicago.

In Chicago the students met up with a group of their peers, seventh and eighth graders from Goethe Elementary School, a pre-K-8 school located in Logan Square on Chicago’s Northwest side.

From right to left, students Tobey Roberts and Emma Williamson, and filmmaker Danielle Mulcahy. — Jeanna Shepard

“When we got there we went to do this thing called whirlyball,” Annabelle said. “It’s essentially like you’re in bumper cars while trying to play lacrosse.”

“And basketball,” Jack added.

They also began filming their experiences. Equipped with go-pros, the West Tisbury students captured everything, from introducing themselves to the five Goethe students that they would shadow throughout their time in the city, to any epic whirlyball collisions.

“It was a great icebreaker,” Mr. Ditchfield said. “It was literally bashing into each other on cars, so you do get to know somebody.”

The students also joined an algebra class and attended a social science fair. The fair, the students found, offered a unique perspective into the lives of some of the Goethe students.

“One student talked about his grandmother immigrating here from Mexico, so he did a project on the history of immigration,” Jack said. “There was someone who lived on the South Side of Chicago who grew up with a lot of gang violence around him. He did a project on the gang database in Chicago and the country.”

The West Tisbury students also conducted man-on-the street interviews with people around the city.

“You’d think people would be closed off in front of the camera, but I think it opened up a lot of adventures for us,” Mr. Ditchfield said. “Especially because 13-year-olds were holding the cameras.”

Film festival artistic director Brian Ditchfield and West Tisbury seventh-grader Jack Lionette. — Jeanna Shepard

During the four-and-a-half-hour drive to Louisville the group set a timer for every hour and a half and pulled off at the nearest random location whenever the alarm went off. Their first destination? Fair Oaks Farm in Indiana.

“It turns out they had an indoor ropes course, a huge bouncy mat, a giant trampoline and climbing walls,” Tobey said.

“And they had a creamery,” Ms. Mulcahy added with a smile. Ice cream, the students agreed, was a huge part of the trip, as they tried different varieties in every place they visited.

“The amazing thing is, during each one of these adventures we’d interview someone there,” Mr. Ditchfield said. The questions varied by location and the students worked together to come up with different topics of interest.

“We were asking questions about what they thought of growing up where they did,” Jack said. “So to the Chicago kids we asked, ‘Do you think Chicago was a good place to grow up? How has Chicago influenced who you’ve become today?’ And then we asked questions like, ‘What advice would you have for the political leaders of today?’”

While the questions elicited a variety of answers depending on location, the students agreed that the same set of values held true regardless of who they were interviewing.

“Treating everyone with respect,” Tobey said.

“And kids talking about being kind to one another,” Jack added. “We met some people that had some different political views from us but we were still able to sit down and have a conversation with them. Even though our views were dissimilar we still could talk without yelling and screaming at each other like so many of today’s political figures do.”

Kentucky served as the final destination for the young filmmakers. The group visited a small town called La Grange, about 25 minutes outside of Louisville.

“It’s the only town in America that has a train that goes right down the main road,” Emma said, while wearing a La Grange T-shirt. Acquiring footage of that train proved to be a difficult feat, as the students waited nearly three hours for one to go by, determined to get the perfect shot.

The students also spent time with seventh-graders from Kammerer Middle School in Louisville. As they talked about their hometowns, the Louisville-natives were incredulous that the Island kids had never eaten Kentucky Fried Chicken.

“The kids from Kentucky really wanted to take us to KFC,” Mr. Ditchfield said with a laugh. While hesitant at first, the West Tisbury students eventually tried the fast food.

With hours of footage now stored on their cameras, iPhones and drones, the students are working on the next stage of the project, deciding whether to create a feature length film, a short documentary, or a series of shorts films. Mr. Ditchfield said the film festival will open up its editing studio to the students one afternoon a week throughout the summer. But, that’s not all he has in mind.

“I think the next extension of this project would be able to bring some of the kids from Chicago and Kentucky here,” Mr. Ditchfield said. “I don’t know if that’s a grantable opportunity like this was, but I hope it is because I think offering those students this opportunity would be really cool.”