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Pour the cream into a large mixing bowl. Add a 1/4 cup sugar and the vanilla extract. Whip into soft peaks.
Cut the corn bread into thin slices. Layer the bottom of a clear glass trifle or other serving bowl with a third of the cornbread. Add a third of the peaches on top of the cornbread and then a third of the whipped cream on top of that. Repeat the layers two more times and crumble the final layer of the cornbread on top.
Refrigerate and serve cold.