2008: Good Masters! Sweet Ladies! Voices from a Medieval Village, by Laura Amy Schlitz - set in 1255 in an English manor village.Have I missed any books? It looks like more realistic medieval settings (and darker stories in general) have been especially popular in the last ten years. Before that, fantasy settings - Ye Merry Old England, or the Middle Ages as we like to imagine they might have been - (like in the tales of Robin Hood) were more popular.
2004: The Tale of Despereaux: Being the Story of a Mouse, a Princess, Some Soup, and a Spool of Thread, by Kate DiCamillo - ok, this is fantasy, but it's set in a castle with a dungeon, and there's a princess.
2003: Crispin: The Cross of Lead, by Avi - set in England in the 1300's.
2002: A Single Shard, by Linda Sue Park - an exception to the usual "merry olde England" setting, since this story is set in 12th century Korea - but the village society and feudal structure are very similar.
1996: The Midwife's Apprentice, by Karen Cushman - another English village in the 1300's.
1987: The Whipping Boy, by Sid Fleischman - like Despereaux, this is set in a fantasy world of castles, villages, and fairs.
1985: The Hero and the Crown, by Robin McKinley - set in a vaguely Arabic fantasy world, with castles and dragons.
1969: The High King by Lloyd Alexander - Prydain is not unlike medieval Europe.
1950: The Door in the Wall by Marguerite de Angeli - between 1350-1370, London and a castle on the Welsh border.
1943: Adam of the Road by Elizabeth Janet Gray - 1200's England - Oxford and several other cities.
1929: The Trumpeter of Krakow by Eric P. Kelly - medieval Poland instead of England!
1924: The Dark Frigate by Charles Hawes - set partially in England in the 1600's, but the inns and blacksmiths and the like are very similar to those in stories set a few centuries earlier.
I do love reading about the past in these books, it's been one of my favorite things about this project. Good thing I like it so much, because historical fiction is apparently really popular amongst Newbery Committee members.
Looks like it's pretty much at least one medieval winner per decade, except for the 30's.
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