Preheat oven to 375F (190C) and line a baking sheet with parchment paper. Set aside.
In the basin of a food processor, combine flour, brown sugar, baking powder and salt. Cover with lid and pulse to combine.
Scatter cold butter pieces over the flour mixture and pulse again until butter pieces are mostly combined but some discernible pieces (no larger than pea-sized) remain.
Combine heavy cream and vanilla extract in a measuring cup and whisk together. Pour evenly over flour/butter mixture.
Pulse again until the mixture is mostly combined and beginning to cling together.
Transfer to a clean, lightly floured surface and sprinkle chocolate chips overtop. Use your hands to gently work the dough together, distributing the chocolate chips as you go, until you have a disc. Fold dough over itself, turn 90 degrees and fold again. Repeat this 4 more times.
Form dough into 2 separate 4” (10cm) discs (for mini scones) or one 6” (15cm) discs (for regular scones).
Using a sharp knife, cut each disc into 8 wedges, pressing straight down with each cut (don’t saw).
Transfer scones to prepared baking sheet, spacing 1” apart. Transfer to preheated oven and bake for 13-14 minutes, until cooked through.
Allow scones to cool on baking sheet. Once cooled, top with vanilla glaze, if desired.
Vanilla Glaze
Whisk together powdered sugar, 2 Tablespoons milk, and vanilla extract. Add more milk as needed until glaze is smooth and drizzles off the whisk.
Dip the tops of cooled scones in glaze or drizzle with glaze. Allow glaze to set before serving.