A group of 26 will cycle from Newcastle to Bathurst over three days from Thursday to raise money for a football club's "trailblazing" health program.
The 365-kilometre ride will support Merewether Carlton Rugby Club's welfare and wellbeing program.
The program supports junior and senior players, coaches and managers to access free psychology and injury services.
President Luke Tresidder said the club had partnered with a Newcastle psychology company for the program.
"We're trying to do the best we can to support our players. We all know mental health is an epidemic," Mr Tresidder said.
Reasons for a player or coach needing help could be a break-up with a partner or the loss of a job, for example.
"A player could have had an injury at rugby and be struggling to get back on the field, or not mentally preparing themselves," he said.
The club, nicknamed the Greens, also sought to ensure that "players aren't out of pocket" when physically injured.
Mr Tresidder believed the club were "trailblazers in player welfare".
"We've provided mental health training to our coaches, managers and senior leadership group," he said.
Football clubs had not focused much on mental health because "we've all been big tough macho footy players".
"You're in a 'suck it up princess world'. At training, you get told what to do and if you don't do it, you're getting barked at.
"The biggest thing is how do you break that culture in a sporting club.
"It's becoming common practice at Rugby Australia and the NRL, but local clubs weren't doing anything."
He said sport was trying to make progress, but "you've got to have a progressive mindset".
"The kids coming through are all trained in mental health. They know it's OK to speak up now," he said.
The club aims to add concussion management to its program.
"We want to give parents confidence that their kid can still play contact sport," he said.
The ride will be about six to eight hours a day.
The cyclists are mostly former players and sponsors, aged from the mid-40s to mid-60s, along with two women, three current players and junior player parents.
Brodie Hussain, who organised the ride, said "it's been a big job to get the event off the ground".
"The logistics of getting 26 riders safely from Newcastle to Bathurst should not be underestimated," Mr Hussain said.
The plans involved "meals, accommodation, kit, back-up vehicles, local approvals and safety assessments".
"It has taken months of planning, training and commitment from the organising group and the riders themselves."
The riders had been training since around Christmas.
"I hadn't been on a pushbike since I was 16. A lot of the guys are in the same position," Mr Tresidder said.
"It's going to be a massive challenge. The goal is to leave as one and arrive as one."
The riders aim to arrive at their destination on Saturday at 2.30pm, in time for the club's trial game against Bathurst Rugby Club.
About $67,000 of their $100,000 goal has been raised. Donations can be made via the Australian Sports Foundation website.
