Preheat oven to 350°F. Grease and line a 9x5-inch loaf pan with parchment paper.
Toss cherries and chocolate with 1 tablespoon flour (taken from the measured flour). Set aside.
Whisk remaining flour with baking powder, baking soda, and salt.
Beat butter, granulated sugar, and brown sugar until light and fluffy, 2–3 minutes.
Add eggs one at a time, then add vanilla and almond extract (optional).
Mix in sour cream, then milk.
Add dry ingredients and mix just until combined.
Fold in most cherries and chocolate (reserve a small handful for the top).
Pour batter into pan, smooth top, scatter reserved cherries and chocolate on top.
Bake 55–70 minutes, tenting with foil if needed, until a toothpick comes out with a few moist crumbs.
Cool in pan 15 minutes, then lift out and cool completely.
Optional glaze: whisk glaze ingredients until smooth and drizzle over cooled loaf.