Mike Cashman hit the road on Tuesday morning, taking the first steps of an epic 12 day 296 km walking journey to Newcastle.
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The 75 year old Tamworth identity has put in 5100 km of preparation for the Holy Grail Walk, as he aims to walk into McDonald Jones Stadium for Knights Old Boys Day next Sunday.
Mr Cashman is also raising funds and awareness for the Men of League Foundation, with a crew of local members joining him for the first few hundred metres.
"I feel pretty good, and am looking forward to an adventure," he said.
"Day one I am walking out to Goonoo Goonoo, which is only 24 km, and should be pretty easy compared to some of the other days I've got coming, but I've done the training and I'm ready for it."
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The retired teacher and avid sportsman is taking the challenge on completely solo, only taking a small backpack and finding accommodation along the way, with the biggest day a 46 km slog from Muswellbrook to Singleton.
Mr Cashman decided to take the challenge on as a way to celebrate his 75th birthday, while linking his hometown of Newcastle to his adopted home of Tamworth.
"The support has been pretty good, and we got some good donations coming in for the Men of League, which is great," he said.
"We won't know exactly how much has been raised until the end, but it all goes to people in the league community that are in need."
Tamworth MoL branch president Kevin Robinson praised Mr Cashman for stepping up.
"Walking 300 km at 75 years of age is not a bad effort, and to raise some money and awareness for Men of League is great."