Wrong-way driver faces multiple charges in fatal December crash on I-89

February 28, 2026 | By Mike Donoghue | Correspondent 

A Jericho man will now face criminal charges, including second-degree murder and 12 counts of aggravated assault, after the wrong-way-driver crash on Interstate 89 in Bolton that killed a woman a week before Christmas, Vermont State Police said Friday.

Timothy J. Wooster, 45, is due in Vermont Superior Court in Burlington on March 12 to face multiple charges connected with events leading up to the head-on crash that resulted in the death of Hailey E. Westcot, 21, of Northfield, state police said. 

Wooster was initially ordered into criminal court for a single felony count of gross negligent operation with death resulting, but the arraignment was postponed earlier this month as the investigation continued by the State Police Crash Reconstruction Team, officials said.

State Trooper Shawn Morrow said the investigation determined that Wooster traveled north in the southbound lanes for about 1.5 miles before colliding head-on with Westcot’s southbound car in Bolton at about 5:22 p.m. on Dec. 17.

State police reported that the investigation determined that Wooster was initially traveling on the northbound side of I-89 in his 2022 Toyota Tundra pickup truck before crossing the median into the southbound lanes. Police have offered no explanation of why Wooster crossed the highway. The incident played out in the stretch of the interstate nearly 10 miles north of Waterbury and several miles south of the Richmond interchange.

The investigation identified at least 12 people who provided statements that Wooster drove past them in the wrong lane of I-89 just before the fatal crash, state police said. That is the reason that 12 counts of aggravated assault and 12 counts of reckless endangerment have been added to the expected charges for when Wooster appears in court, officials said.

State police said Wooster’s defense lawyer received a citation Friday ordering his client into criminal court next month. Attorney Robert Kaplan of Burlington said he had no idea what the state is relying on to add the murder charge and the 12 counts of assault and reckless endangerment. He said the only paperwork state police provided was a half-page citation form.

More details from investigators will be shared at the time of Wooster’s court hearing.

A tractor-trailer also was involved in the crash. Douglas Bailey, 50, of Londonderry, New Hampshire, was driving southbound in a 2024 Cascadia Freightliner. 

The events unfolded as Westcot was traveling southbound when her sedan was first struck by Wooster’s northbound vehicle, and then it collided with the tractor-trailer in the southbound travel lane, police said. The collision with the tractor-trailer caused Westcot’s car to roll over and sustain further damage, Morrow added.

Westcot, who was wearing a seatbelt, died at the scene, and her 2018 Kia Sportage was demolished, Morrow said.

The weather was clear and dry at the time, police said. The crash brought southbound rush-hour traffic to a halt. That side of I-89 was eventually shut down for about five hours, with vehicles at a standstill for miles.

Wooster was apparently headed home from work in Montpelier, where he is a partner in a financial management firm. He has worked in the banking and portfolio business for 20 years.

Westcot also was on her way home that evening from O’Brien’s Aveda Institute in Williston where she was in training to become a cosmetologist. 

Wooster, who was wearing his seatbelt, sustained serious, non-life-threatening injuries and was taken to the University of Vermont Medical Center. His pickup was demolished due to front-end damage, police said.

Bailey, the tractor-trailer driver, also was wearing a seatbelt and was uninjured in the crash. His rig received heavy front-end damage, police said. 

Williston Police and Fire Departments, the Department of Motor Vehicles DMV Enforcement & Safety Division, Bolton Rescue and Richmond Fire & Rescue all responded to the crash in addition to state police.
According to her obituary, Westcot grew up in Randolph and attended school there. She excelled in her studies and received accolades for cybersecurity training through the criminal justice program at Randolph Technical Career Center. Following high school graduation in 2023, she began working at Northfield Elementary School as a custodian and attending O’Brien’s Aveda Institute. 

A little more than a year before the wrong-way crash, Westcot’s mother, Beverly Dezotell of Randolph, also died in a crash on I-89. She was a passenger in a single-car accident on Oct. 16, 2024, on the interstate in Williamstown.