LiquidOxygen80: Age of Rifles, Age of Sail, a veritable cornucopia of WWII era games. Sid Meier's Gettysburgh/Antienam.
Just a bit of clarification, though? Do you mean games actually rooted in history, or games that are placed in a historically accurate time frame? Or something more educational, like say, Where In Time Is Carmen Sandiego?
Profanity: Placed in a historically accurate time frame, historically accurate events. Not some alternative dimension story, in "insert time frame".
I really doubt I'd enjoy an educational game... I usually end up being creeped out by how the developers of educational games think you're a bloody retard. Or maybe I've been unlucky enough to stumble upon the worst ones.
Gotcha. You could try out Sid Meier's Colonization. Think Civ during European exploration of the New World. It runs perfectly fine on D-Fend and I believe Abandonia has it listed as freeware.
As for education titles? The ONLY reason I played them is because my parents back then thought that we'd learn better if we thought we were playing games too. >.>
So I had to play Mavis Beacon Teaches Typing, Carmen Sandiego, Super Solvers, you name it. :(
HORRIBLE TIMES. HORRIBLE. Edutainment, my butt.