Police say a ‘substantial four figure’ sum of cash was taken from the Dumfries Labour and Social Club in Lochside Road at about 3.20 am on Thursday.
PC Paul Murphy said: “We have a description of a man who was seen near the premises around this time and we are keen to trace him.
“He is described as being around 5’9″/5’11” tall, slim build, wearing a light coloured casual jacket, waist length with epaulettes, a hooded top underneath, jeans and trainers.”
He added: “We are carrying our door to door enquiries and want to hear from anyone who can help us trace whoever is responsible for this crime.”
The second break-in was at the former Stakeford Inn in College Street in the town.
It occurred some time between Monday and Wednesday.
The premises are currently being converted into a house.
A yellow coloured Karcher pressure washer valued at £1000 was stolen in this raid.
PC Kevin Smith wants to hear from anyone who may have seen anything suspicious in the area between Monday and Wednesday.
Callers can pass information to Police Scotland at Dumfries on the 101 number, or if they want to remain anonymous then through Crimestoppers on 0800 555 111.