North Yorkshire County Council has been forced to spend almost £1.5m on repairing and improving the A59 at Kex Gill since 2009.
Figures, obtained through a Freedom of Information request, revealed the county council has spent £912,000 in seven years to protect it from adverse weather.
However, NYCC shut the route in January due to the risk of a landslide after cracks were found on the hillside following heavy rain over Christmas.
A further £550,00 has now been spent on installing a drainage system and the county council are hoping to open the road again on March 7.
In 2014, the road underwent £200,000 of work to protect it from landslips just two years after it was last resurfaced and nearby banks were strengthened.
Coun Don Mackenzie, executive member for Highways, explained that the road's construction meant it was susceptible to land slippage following wet weather.
He said: "The major problem is that the roads are built on a ledge of a steep slope. That road arrangement lends itself to pretty high maintenance costs.
"It's inevitable that you get these difficulties with steep slopes. In 2011, the county council spent a considerable amount of money on improving drainage and in 2016 we are having to return to this.
"I'm hoping these works give us as long, if not longer, than the resurfacing five years ago. I'm hoping this time we have resolved the situation for longer than five years."
The closure of the road since January and the seven-and-a-half week programme of work has been a source of frustration to motorists and businesses along the route.
Coun Mackenzie said he was conscious local residents were being inconvenienced by the road's closure and that businesses relying on passing trade were being badly affected.
As a result, he is hoping his recently published Strategic Transport Prospectus for North Yorkshire will be approved at a county council meeting on Wednesday.
If approved, one of the priorities of the prospectus would be a £33m scheme to deliver a major re-alignment of the road.
Coun Mackenzie said: "One of the reasons we want to get away from Kex Gill is the constant maintenance it requires.
"It's not only the cost of the works, it's the cost on industry because of the businesses on the route.
"It's a fairly long diversion and it affects the passing trade of local businesses along the route. It adds half an hour on to journeys for other members of the public.
"But, if we do adopt it, it does not mean we have the funds to do the work. But, it's the first stages in going to government to apply for funds to carry out the work."
Coun Mackenzie admitted the scheme could take a number of years to come to fruition but said the plans had been backed by a number of local MPs.
Julian Smith, MP for Ripon and Skipton, has supported the plans and has announced a meeting with the county council's Executives over the issue.
At this meeting, the Conservative MP said he will formally launch the 'Kex Gill Bypass Campaign' after describing the recent disruption as 'unsustainable'.