McSheffrey, who was a free agent after leaving Coventry City, has agreed a four-month deal after training with the club.
In an exclusive interview with Spireites Player
, McSheffrey said: "I could have just seen out my contract at Coventry and picked up my wages every month but the manager here has given me the opportunity to play football. I plan on taking the opportunity with both hands.
"The squad is very impressive and there's a good feeling about the place. The manager has a philosophy of total soccer and the lads play some good football. It's a club that's only going one way."
The initial agreement will keep McSheffrey at the club until January, making him available for the busy festive period. If all goes to plan, the 31-year-old could then sign a long-term contract.
He said: "It's good for both parties because it gives me an opportunity to start playing again and the club can take a good look at me over the next few months. There's a strong possibility that it could be turned into a permanent arrangement."
After starting his career at Coventry, McSheffrey moved to Birmingham City in a deal worth around £3.5million in 2006. He rejoined the Sky Blues three years ago after spells on loan at Nottingham Forest and Leeds United.