Hotel bosses have had to wait more than a year for the thatcher to be able to do the work at the hotel near Shifnal.
The £40,000 project will see the grade-II listed building repaired for the first time in more 50 years.
Owners of the family-run Hundred House Hotel, in Norton, have now ploughed more than £1 million into renovating the property since moving into the venue in 1986.
The hotel is still run by Henry Phillips, 75, while his sons David, 52, and Henry, 49, run the maintenance and kitchen side of the business.
Much of the interior and design work of the property was carried out by Henry’s late wife, Sylvia.
David said: “The work will probably take two weeks to complete. The last time it was thatched was in 1961.
“The hotel was once a court and there are still stocks and a whipping post in the gardens.
“The tree where people were hanged is still in the garden and the former prison is now part of the beer cellar.
“Work on the roof will cost the best part of £40,000 and it’s taken us one-and-a-half years to get the thatcher here.
“We’ve just found out some of the timbers are a bit rotten.”
The work on the barn roof will be carried out by Shrewsbury-based master thatcher, Paul Draycott.
David said the family were still deciding what to do with the listed barn because it could not be changed much due to its historical context.
“When we moved here in 1986 the hotel was derelict but over the past 28 years we have restored it,” he said.
Ten years ago we renovated the tithe barn, which is now used for functions and weddings. We wanted to preserve this barn but in the longer term, because it’s listed, there is very little we can do with it,” he added.
“We did consider using it as micro-brewery but we’re still unsure.”
The family had previous renovated and run the Greyhound in Buckinghamshire before moving to the Hundred House in 1986.
The restaurant was opened during the same summer and the rooms were opened in January 1987.