The six-time premiership player and four-time premiership coach, now 75, will set off on a six-day, 400km charity cycle around country Victoria on Tuesday.
He'll be joined by two of his former North Melbourne charges, Peter 'Crackers' Keenan and Wayne Schimmelbusch, with the trio set to complete the ride for the third time.
Making his first appearance on the testing journey will be Collingwood 1990 premiership defender Michael Gayfer.
The group will raise money for St Mary's House of Welcome, a refuge for the homeless and disadvantaged in Fitzroy.
Keenan, who won a flag under Barassi at the Kangaroos in 1977, said his former leader would still be firmly in charge once the group set off from their starting point of Timboon, in Victoria's south-west.
"Every morning it's, 'Get out of bed, come on, get moving 'Crackers', get a wriggle on'," Keenan said.
"And that's what we do.
"He's still bossing us around, don't worry.
"I'll go into a nursing home one day and he'll find out where I am and he'll come and boss me."
In response, the master coach delivered a typically frank assessment of his riding partners' performance during training.
"They're trying very hard," Barassi said.
"I wouldn't say they're going at unbelievable speeds, but they're doing fantastically well.
"If you listen to 'Crackers', you'll believe that he's doing unbelievable speeds, but I'm telling you he's not."
Keenan, Barassi and Schimmelbusch have all paid visits to St Mary's.
Keenan said he was happy to help a worthy cause.
"I have seen first-hand the good things that St Mary's House of Welcome does for people in need," Keenan said.
"You go down there to Brunswick Street and you can see people getting fed and being counselled.
"They are given back their dignity, with St Mary's creating a social network for them."
From Timboon, the riders will travel to Port Campbell.
They'll then pass through Colac, Apollo Bay, Torquay and Queenscliff, where they'll ferry to Sorrento ahead of the final leg to Elwood on Sunday, November 20.
The group's arrival in Elwood Park will coincide with another St Mary's House of Welcome fundraiser, 'Wine Rules'.
For more information on the Footy Greats Charity Bike Ride or Wine Rules, or to donate, visit www.smhow.org.au.
