"My Great great grandfather was Colonel John Reynolds Winston of the 45th"

Is he the one who escaped by walking across a frozen lake to Canada?
Then on to Halifax to take a ship to Wilmington.

Do you know the name of that ship which slipped through the blockade and when he escaped?

It's possible that a family member of mine(father's side) was on the same ship as he was during that trip.

That would link my father's side and mother's side in a way.

My father's side were Cape Fare pilots and blockade runners.

There was a "Pirate" ship/raider, the CSS "Tallahassee" and several other ships that my father's side made that trip to Halifax on.
The Yankees name her a Pirate ship because she flew the stars and strips sometimes to lure other ships close so she could seize or sink them.

Other ships to name a few are the....

"Hansa"

"Beatrice"

"Wando(Let her rip)"

"Owl"

"Let Her Be(Chicora)"

"Banshee"

"Hebe"