Richard Yates, of Middleton Scriven, near Bridgnorth, said "unsustainable" milk prices, huge bills to upgrade his electricity supply, and the impacts of the coronavirus pandemic have all contributed to his decision.
The 54-year-old runs a mixed farming operation but said he had been thinking of moving away from dairy "for some time".
He said: "It has been a rewarding career and I leave with a heavy heart. I have empathy with the animals. They work very hard for us. I have always said I prefer things with four legs than four wheels.
"I have a 40-year-old parlour which needs updating and to upgrade my electricity supply could cost me the thick end of £100,000.
"We have had one of the wettest winters on record and the coronavirus has had a big impact on farming operations."
He said dairy farmers were in "a vulnerable position" as they had to take the prices offered to them.
And because cafes and restaurants up and down the country have been forced to close closed, some farmers were having to pour their milk down the drain.
"The milk price I am getting is the same as what it was last century which is unsustainable," Mr Yates said.
"I think the critical deciding factor in my decision was when my milk supplier announced that from October it would be moving to an every other day collection, which would mean I would need a bigger storage tank."
Mr Yates is a former chairman of Shropshire NFU and runs three farming operations within the county.
He is the son of Henry Yates who passed away in February.
"The death of my father made me have a good look at my business," he said.
"I followed my father and grandfather into dairy farming but I have two daughters who don't want to go into the industry.
"I have got up at 5.30am every morning, worked every weekend and even Christmas Day.
"Cows always have to be milked which has meant I have not always been able to go and watch Bridgnorth Rugby Club when I have wanted to.
"I thought now was the right time to do things easier."
Mr Yates has now sold 40 of his 100-strong herd to a larger dairy operation in nearby Ludlow, with another 40 finding a new home at Evesham in south east Worcestershire. He is retaining a small suckler herd of 20.
"I have still got three farms. I could extend my sheep flock or plough up fields and turn them into arable," he added.
"I shall retain a very keen interest in agricultural matters."
Mr Yates believes dairy farming still has a future – despite his decision to quit the industry.
"I think we will see farm sizes increasing and more farms adopting new technology. But this will come at a cost," said Mr Yates.
"I hope more grants become available and the Government backs farmers to utilise this technology.
"Dairy farming is so dependent on passing TB tests. Unless the industry really grabs hold of the issue farmers will continue to work with one hand behind their backs."