“The idea first started with me doing a show at the top… and I thought ‘I could do it while I’m walking up’,” he said.
“I thought: ‘Carrying the speaker, that could make it a challenge’.”
Despite being diagnosed with chronic lung condition Emphysema last year, he said he was confident he could climb the hill, which is 1,335ft (407m).
“It’s in the medium stages, so it does affect some of my more physical activities,” he told BBC Radio Shropshire.
“I wouldn’t say I’ve noticed it affecting my stage performances… I jump around a lot, I rap loads of words a minute.
“An average walk up the Wrekin is maybe 30 minutes to an hour, so I’m hoping to do it in less than an hour and a half.”
Mr Rogers has already started training for it by walking with about half the weight in a backpack.
“It is difficult,” he added.
He said he wanted to raise money for the charity because it went “above and beyond for the local area”.
“The people they’re touching, the young people they’re impacting on, the lives they’re changing, the support they’re offering… it goes beyond what they say they do on the website.”