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Former Massachusetts boarding school teacher accused of sexually assaulting student from Wilton

The victims say Rutledge started grooming them when they were 15 years old and maintained a relationship with them after they graduated.

Rose Shannon

Apr 23, 2026, 9:30 PM

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A former teacher at a prestigious Massachusetts boards school pleaded not guilty Wednesday to sexually assaulting two former students, including one originally from Wilton.

Matthew Rutledge is accused of assaulting the women in the early 2000s at Miss Halls School in Pittsfield.

The victims say Rutledge started grooming them when they were 15 years old and maintained a relationship with them after they graduated.

Former News 12 Connecticut intern Melissa Fares told Vanity Fair that Rutledge even visited her at her family's home.

Prosecutors initially declined to bring charges in 2024 because Massachusetts law does not make it a crime for teachers to have a sexual relationship with a student over the age of consent which is 16.

"I think a lot of people don't understand that it takes a long time to understand that what you have lived through is trauma. So many survivors have been groomed," says Fares.

Fares and another victim, Hillary Simon, have been lobbying Massachusetts lawmakers to change the law.

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