A dozen horsemen and four carriages will take to the road on Hallowe'en and ride from Goldthorpe to Barnsley.
They are raising money for Regan Beevers, 14, Doncaster Road, Kendray, who needs a wheelchair after he was born with a rare disorder which causes joint deformities, inability to walk properly and muscle weakness.
Dawn Robinson, of Railway Terrace, Goldthorpe, has organised the spooky ride and is hoping to raise £5,000 for the Dearne ALC pupil.
Her son Jordan, 13, is good friends with Regan, and both are taking part in the ride.
"There's about 12 riders that have said they are coming and four carriages in total. We're all going to be in Hallowe'en costume so we hope it'll be quite a sight," she said.
"We're setting off at 9.30am and we're going to ride on the A635 towards Barnsley.
"We'll go to the Riding for the Disabled school for a bit of a break and let everyone catch up.
"We're going to go through the town centre somehow so hopefully lots of people will see us and want to donate for Regan."
Dawn, 52, who has Bridal Lane Stables, asked friends she knew with horses to take part and said Regan would be driving in a carriage with a pony called Chico.
She said they would be stopping at various points and asking people to sponsor them.
"The council said we couldn't have collection buckets as it might hold up the traffic so we're hoping people will sponsor us instead.
"Regan's a lovely boy and we really want to raise enough money to help him out. Him and Jordan are like brothers they are so close. His mum thinks it's a great idea so fingers crossed everyone gets behind us on Hallowe'en."