Brandon Harris targeted the stores to steal cigarettes and vodka leaving the shop staff terrified.
Today Harris, 23, of Witham Street, Boston, was jailed for three years and four months.
He admitted robberies of the Pasikonik Store in New Street; a Spar Shop on London Road; and a Co-Op store on Argyle Street. He also admitted theft, possession of an offensive weapon and breach of a conditional discharge. Harris asked for a further three offences to be taken into consideration including two thefts and a robbery.
Phil Howes, prosecuting, told the court "During each of the robberies he had a weapon to cause fear."
Mr Howes said that the first robbery was at the Pasikonik Store on March 11 when Harris approached the counter with his face covered and a hood over his head.
"That didn't attract the attention of the assistant on the till because of the Covid 19 position, " said Mr Howes.
The shop assistant opened the till and Harris grabbed some cash before making off. Another member of staff chased him and managed to wrestle with him but he got away.
Harris was subsequently arrested and charged with the robbery but was then granted unconditional bail by magistrates.
On the night of his release on bail he stole cigarettes and drink from the Aronia Store in High Street, Boston and then ran off.
The following evening Harris held up the Spar Shop on London Road producing a broken bottle at the shop assistant as he demanded "Give me baccy".
Mr Howes said "His face was covered. She initially thought it was a joke but then realised she could be harmed. She managed to press the panic alarm. He partially left but then returned and helped himself to 10 packets of cigarettes."
On the night of Sunday, March 15, Harris went into the Co-Op on Argyle Street as staff were preparing to close for the evening. Harris, who was armed with a metre-long pole, pointed the weapon at staff and then took cigarettes from the display running off. The shop assistant knew Harris, who was a regular customer at the shop, and as a result he was arrested later the same day.
Neil Sands, in mitigation, said "His life has been blighted by drugs.This is a young man who at the age of 16 got in with the wrong crowd and that led to involvement with drugs.
"He is deeply ashamed and embarrassed by what he did. He regrets it bitterly and expresses a desire to apologise to his victims."
Mr Sands said that since being remanded into custody Harris has been able to avoid drugs and has been taking steps to improve his life."