Prep Brie or other soft-bloomy-rind with cut-out shape, and place on board. Place Champagne cheddar on board and break apart into pieces and pile inside the rind. Cut Sage Derby into cubes and create pile on board. Slice and arrange remaining cheeses on board.
Shape charcuterie into ruffles or layers and place on board.
Arrange remaining ingredients on board. If crackers fit on the board, add them, otherwise serve crackers alongside board.
Garnish with fresh rosemary sprigs and small cut-out shapes from cheeses.