"It's someone that knows the store and had been in and saw the deadbolts had been taken off and thought 'cool, I'll be back'."
The burglars had not been deterred by the security lighting or cameras, Mr Kershaw said.
"It's all lit up and it's got cameras, it's not like it's dark. They were really boisterous, they just don't care."
Staff had been shaken by what was the third break-in at the store in 18 months, Mr Kershaw said.
"It's put a little bit of fear into everyone, as far as the team goes. If something is that valuable in the store we don't want to see someone being held up for cigarettes."
Rising prices were making cigarettes even more of a target for thieves, Mr Kershaw said.
"We are considering not stocking cigarettes, we don't take that lightly, and we think it's only going to get worse for businesses come January next year when prices go up to $30."
The store had lost thousands of dollars in stock and would also have to fork out for repairs, leaving it tens of thousands of dollars out of pocket, he said.
"[We] run the risk of obviously having our insurance company taking a hard look at us to see if they are even going to re-insure us because it's the third time."
Martinborough residents were fed up with what Mr Kershaw said was a recent "spate of petty crime".
"It's not what Martinborough is about. We've had a real spate of petty crime lately and it's frustrating and we are all getting sick of it as locals.
"It's the third time in 18 months it's happened and there's a strong correlation with the fact that we haven't had a cop [in town overnight]. It's opportunistic. They are just little thugs.
"They've sussed it out - they know the cops are a minimum of 15 minutes away by the time the call goes through and it's easy for them to see if the police car is there [in the town] or not.
"We had a 30-year stretch with no break-ins and then three in 18 months. It's just such a massive distraction from what we should be doing day to day. It's frustrating."
The store would be beefing up security as well as making the cigarettes harder to access, Mr Kershaw said.
He urged anyone with information to come forward.
"The police have been great so far and we really want a prosecution."
South Wairarapa Police Sergeant Richie Day said police would like to speak to the owner of a white sedan seen in the area about the time of the break-in.
"If anyone has any information about the vehicle, burglary or has been offered cheap cigarettes to purchase, then please contact Crimestoppers or police."