ASHFORD, Windham County, Conn., Nov. 7, 2026 — A Massachusetts man died and an Eastford woman was critically injured in a head-on crash on Route 44 late on Thursday night, November 5, according to Connecticut State Police.
The crash happened near Pumpkin Hill Road shortly before 11 p.m. Investigators said the woman's car was traveling in the opposite direction from the man's vehicle when it reportedly crossed the double-yellow center line and struck his car head-on.
The 82-year-old Agawam, Mass., man was pronounced dead shortly before midnight at Windham Hospital. The Eastford woman was taken to Day Kimball Hospital with serious injuries. Her condition and the man's next of kin, who have been notified, were not detailed further in the release.
Route 44 was briefly shut down in the area while crews worked the scene. State police said the road has since reopened and the scene is no longer active. The crash remains under investigation.
Our sympathies are with the family of the person who lost their life.
More on Crashes in Ashford, CT
This fatal crash happened on Route 44 in Ashford, CT. We cover crashes across Windham County as they're reported, and you can browse the latest in our Windham County accident reports.
Frequently Asked Questions
How can drivers avoid being involved in a head-on crash?
Staying attentive, keeping a safe distance from the center line, and slowing down on curves or unfamiliar roads can help drivers react in time if an oncoming vehicle drifts into their lane.
Where do head-on crashes usually happen?
They're common on two-lane rural roads and highways without a median, where there's little separation between opposing lanes of traffic.
Why is passing a factor in head-on crashes?
Attempting to pass on a two-lane road puts a driver temporarily in the oncoming lane, which can lead to a head-on collision if timing or visibility is misjudged.
Do median barriers help prevent these crashes?
Yes. Physical barriers between opposing lanes keep vehicles from crossing into oncoming traffic, which is why they're commonly added to busier stretches of highway.
