Bill Henningsgaard left in his small plane from Teterboro Airport in New Jersey with his son Maxwell on Friday morning. They were taking the short trip to Connecticut to tour the last college on their list, Yale. Maxwell was scheduled to graduate highschool in 2014, and they had been flying across the country visiting different college campuses.

At the same time, a woman and her two children, ages 1 and 13, were going about their normal morning routine at their house in East Haven, Connecticut, about half a mile from Tweed New Haven Airport. According to authorities, the mother was in the front of the house and the children were in the back.

At around 11:22 a.m. something went terribly wrong with Henningsgaard’s plane, and it went down striking one home before crashing into a second with the family inside. While the mother survived, the two children are believed to have died in the home. Henningsgaard and his son were also killed.

“We are doing everything we can for the mom,” Mayor Joseph Maturo of East Haven said. “Our hearts go out to her and her family.”

Gov. Dannel P. Malloy said, on Friday afternoon, that there may be as many as five victims, but Robert Gretz, an investigator with the National Transportation Safety Board, said, at a news conference, that there could possibly have been as many as six; three in the plane and three on the ground.

It is believed that Henningsgaard have tried to land the plane, but was unsuccessful and was making another attempt when the plane crashed. “It appears that there was a first approach,” Mr. Mallow said. “For whatever reason, that approach was not executed.” There was no distress call and no evidence that the plane may have run out of fuel.

59-year-old Chris Dogolo, was at home and witnessed the crash. “There were people running down the street panicking,” Dogolo said. “A lady was screaming that there were two kids in the house.”

This was not Henningsgaard’s first plane crash. In 2009, Mr. Henningsgaard, was flying in a single-engine plane with his mother, when it went down in Washington’s Columbia River. He and his 84-year-old mother were rescued by a passing boat as the plane began to sink.