Wash all produce. Slice the watermelon and provolone cheese, then use a small star-shaped cookie cutter to punch out festive shapes.
Place three small bowls on a large wooden board to hold the dark olives, pomegranate seeds, and any wet ingredients.
Fold the beef soppressata and beef pepperoni slices into ribbons or rosettes. Fan them out around the anchor bowls to create an S-curve across the board.
Distribute the cubed white cheddar, sliced Havarti, and star-shaped provolone evenly, breaking up the red sections.
Fill out the board by clustering the red items (strawberries, raspberries, cherries, tomatoes, radishes) and blue/dark items (blueberries, blackberries) in alternating groups.
Tuck the assorted crackers and almonds into any remaining empty spaces. Garnish with a final sprinkle of pomegranate seeds.