Combine feta cheese, cream cheese, yogurt, lemon juice, Greek seasoning, garlic, dill, and black pepper in a food processor. Blend until smooth. Transfer to a bowl and garnish with red pepper flakes. Refrigerate while you assemble the board.
Place pickled cauliflower, artichoke hearts, pickled okra, hummus, and olives in separate small serving bowls. Arrange bowls on a large cutting board or platter. Add dip bowl.
Arrange some of Cheddar cheese, tomatoes, grapes, carrots, bell peppers, cucumber, crackers, pita chips, salami, pepperoni, almonds, blackberries, and chickpeas around the bowls, without overcrowding. Keep extra ingredients in covered containers in the refrigerator so you can replenish the board as needed.