The tall forward, who joins from Marske United, has played professionally at Hartlepool United, Preston North End, and Cork City, with loan spells at Carlisle United and Accrington Stanley.
Simpson has also gained valuable non-league experience with fellow Northern Premier League sides Lancaster City and Hyde United.
Simpson, who has also spent time with Welsh Premier League outfit Connah's Quay Nomads, told whitbytownfc.com: "Hopefully, coming into the team, I can provide a lot of goals. When speaking to the management, that's the main problem at Whitby.
"When we played against Whitby when I was at Marske, they created a lot of chances but for some reason they couldn't put it in the back of the net. That's what I feel I can do.
"My main strength is being in the box and my meat and drink is when you get balls into the box. I can also get it down on the floor so I'm not just used as a 'head on the stick' as I've been called before. I can mix it up."
Whitby Town manager, Nathan Haslam, added: "Connor was someone me and Lee (Bullock) looked at in the summer. He went to Marske but he's found himself surplus to requirements.
"We're lacking goals and the idea with Connor coming in is that he's got a fresh start and he's a big lad who's good on the deck. He gives us options."
Simpson is eligible to feature in Saturday's league match at home to Atherton Collieries.