A Vineyard Haven man has pleaded guilty to vehicular homicide charges connected to the death of a 22-year-old woman in a head-on motor vehicle collision last winter, receiving additional jail time after a judge rejected the conditions of a plea deal.

Zachary Dupon, 26, of Vineyard Haven pleaded guilty to Dec. 19, 2020 charges in Vineyard Haven of motor vehicle homicide by reckless endangerment. Mr. Dupon was sentenced to two and a half years in a house of correction, two years to serve. The six-month balance of the sentence will be suspended for two years, according to Edgartown district court clerk-magistrate Liza Williamson.

During the time of the suspended sentence, Mr. Dupon will be placed on probation. Conditions include no driving, staying away from the victim’s family, participation in the brains at risk program and 40 hours of community service.

Mr. Dupon was also found responsible for marked lanes violation and speeding charges, with both placed on his record. Because he was not indicted, he will likely serve his split sentence at the Edgartown house of correction, according to Ms. Williamson.

The Hon. Benjamin C. Barnes presided over the plea on Friday, August 27.

Mr. Dupon has 68 days served credit, according to district court filings. Two and a half years is the maximum sentence for cases prosecuted in district court.

The disposition in the case comes after months of back-and-forth between Mr. Dupon’s counsel, attorney Rachel Self, and assistant district attorney Michael Palazollo. The two sides had agreed to a plea deal on the vehicular homicide charge that included two and a half years in a house of correction, witha year and a half served.

But Judge Barnes rejected the prosecution’s recommended sentencing after hearing substantial testimony from the family of victim Emma Hall, according to Ms. Williamson. Judge Barnes’s sentence included six additional months of time served.

The case stems from a fatal motor vehicle collision on Beach Road in Tisbury last winter. Mr. Dupon collided head-on with Ms. Hall’s vehicle while passing cars in the southbound lane.

Ms. Hall was declared dead at the scene, and two other passengers in her vehicle were treated for injuries. Mr. Dupon did not sustain serious injuries.

The incident caused ripples of grief in the close-knit Island community, where both Ms. Hall and Mr. Dupon and their families are well known.

Ms. Hall graduated from the Martha’s Vineyard Regional High School in 2017. Mr. Dupon graduated from the Martha’s Vineyard Public Charter School in 2013.