Oak Bluffs police arrested an Edgartown man on an operating under the influence charge Saturday after he allegedly crashed a truck into two buildings and a car parked along Circuit avenue.
An Edgartown man has been charged with operating a vehicle under the influence of alcohol after allegedly crashing a truck into two buildings and a parked vehicle on Circuit avenue Saturday.
Theodore Bennett, 43, was arraigned in Edgartown District Court Monday morning, where he pleaded not guilty to charges of operating a vehicle under the influence, leaving the scene of a property damage accident, negligently operating a motor vehicle and improperly operating a motor vehicle.
Police allege he was driving a gray Toyota Tacoma northbound on the street around 7:15 p.m. Saturday when he hit 145 Circuit avenue. He then proceeded on to hit a parked car and Third World Trading Co., a clothing and gift store at 52 Circuit avenue.
According to the police report from the incident, Mr. Bennett was found in the truck’s driver’s seat with glassy eyes and an odor of alcohol. He was slurring his speech, was unwilling to answer questions about where he came from and failed sobriety testing, the police wrote. He also allegedly claimed he had not been drinking and refused a breathalyzer test, at which point authorities seized his driver’s license.
“Bennett did not seem to grasp the severity of the situation,” the report reads.
Mr. Bennett was allegedly struggling to calm himself down and told officers he suffers from PTSD.
Mr. Bennett posted $1,000 bail and agreed at his arraignment to submit to alcohol testing, not consume alcohol and abstain from operating a motor vehicle.
Oak Bluffs police chief Jonathan Searle confirmed to the Gazette soon after the incident that there were no reported injuries. According to police, Mr. Bennett was the sole occupant of the vehicle and refused medical attention.
Third World Trading Co. was heavily damaged in the crash. Much of the shop’s facade was destroyed when the truck ran into it, including the front steps, front wall, windows and merchandise. The roof also appeared to have incurred damage.
The front stairway and lawn at 145 Circuit avenue were damaged in the first collision, according to the police report.
The police report also says that a woman was showering upstairs at Third World when the truck collided with the building, causing her to hit her head.
Video footage from a nearby webcam shows the truck headed in the wrong direction up the one-way street before running into the store.
In 2017, Mr. Bennett was charged with operating under the influence of drugs, but those charges were dismissed.
Mr. Bennett’s pretrial hearing in the case is scheduled for Jan. 15.
Editor's note: this article has been updated with information from Mr. Bennett's arraignment.

Comments
I thought circuit Ave was one
Tom Engley West TisburyI thought circuit Ave was one way.
While headed in the wrong
robert skydell antigua, guatemalaWhile headed in the wrong direction on a one-way street.
Luckily no one was injured.
NOW that's a distracted
Sisyphus OBNOW that's a distracted driver!
My heart goes out to the
Susan Desmarais Oak BluffsMy heart goes out to the owner of Third World.
Well said “ my heart goes out
Joe Barkett EdgartownWell said “ my heart goes out to third world” it has always been there ( for my 30 + years here) I always stop in a few times and always come out with something interesting.
I do hope that re-building is in their future .
I feel bad for those impacted
Ellen Cantin EdgartownI feel bad for those impacted and involved and for the driver's family. This isn't his first court appearance. I hope it's a true wake up call for him before others get hurt.
My wife and I owned that
Hollis Engley Mashpee MaMy wife and I owned that building in the ‘70s, when we operated Gallery Camera. Before us it was the Blakesely Gallery of artists Bill and Ginny Blakesly. Its vintage is more or less the same as the Campground cottages, so it’s not particularly sturdy. It’s no surprise that the collision seriously damaged at least the front of the building.
Lori. This is just terrible.
Chris Huff Vineyard HavenLori. This is just terrible. So sorry. You can rebuild, it’s OK. At least no one was hurt.
Let's all make sure to
Julian Wise ChilmarkLet's all make sure to support this wonderful business when it reopens to make up for their lost holiday season. And people- cars belong on the road, NOT inside stores.
So this is what ‘dismissing a
Renee DuttonSo this is what ‘dismissing a DUI/drugs’ leads to…more dui’s! I hate that charges like that get dropped! Very frustrating!
Glad no one was hurt or killed. A big hit to store at Christmas time:(
I understand the frustration,
Patrick J EdgartownI understand the frustration, but jail time alone doesn’t necessarily prevent repeat offenses. In fact, studies show that treatment-based approaches are often more effective at reducing recidivism for DUI and substance abuse cases than incarceration alone.
If there was a previous dismissal, it likely came with conditions like mandatory treatment, counseling, or monitoring programs. The real issue is ensuring those programs are completed and effective, not just whether someone serves time.
I’m not excusing Mr. Bennett’s actions - he absolutely needs to be held accountable and should face consequences for putting people at risk. But if this is addiction-related, we need a combination of accountability AND treatment to actually break the cycle. Just locking someone up and releasing them without addressing the underlying issue often leads to the exact situation we’re seeing here.
It’s a tough balance, and I agree it’s incredibly frustrating - especially when local businesses suffer the consequences right before the holidays.
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