Preheat the oven to 375°F (190°C). Line a baking sheet with parchment paper or a silicone baking mat.
In a stand mixer fitted with the paddle attachment (or by hand), stir together the flour, granulated sugar, baking powder, baking soda, and salt.
Meanwhile, in a small bowl, whisk together the buttermilk, egg, orange zest, and vanilla.
Add the butter to the flour mixture and stir on medium-low speed until the pieces of butter are the size of chickpeas.
Stir in the buttermilk mixture and mix on low speed until the dough begins to go from shaggy to starting to form a solidified mass. Add the cherries and chocolate chips and mix just until the dough comes together.
Turn the dough out onto a countertop dusted with flour and knead it very gently two or three times to bring it together. If the dough is too sticky, add another tablespoon of flour, although scones turn out better when the dough is on the humid side, so add it only if it feels really wet.
Use your hands to pat the dough into an 8-inch (20cm) circle. Cut the circle into eight equal-size wedges with a chef’s knife or pastry scraper.
To make the topping, mix the granulated sugar and cinnamon together on a small plate. Press the top of each wedge heavily into the sugar mixture and set the scones, sugared side up, on
the prepared baking sheet as you go, spacing them ½ inch (1.5cm) apart—because scones like to be baked close together.
Bake until the scones feel firm to the touch on top and lightly golden brown up the sides, about 15 minutes. Let cool completely.
To glaze the scones, mix together the powdered sugar, milk, and vanilla paste in a small bowl until smooth and creamy. Spread or drizzle the glaze over the scones.