Combine the Madeira cake and chocolate sandwich cookies in a food processor. Pour in the melted milk chocolate and blend until a thick dough forms, about 2-3 minutes.

Roll the mixture into approximately 10 walnut-sized balls, tightly packed. Place on a tray, cover with plastic wrap, and chill in the refrigerator for 2 hours.

Insert a wooden skewer into each chilled cake ball halfway. Melt the white chocolate in a double boiler until smooth; dip each cake pop ensuring even coating.

Press a sugar-coated chocolate bean onto each pop while the chocolate is still wet. Place the pops upright in the pumpkin or squash.

Chill the decorated cake pops in the refrigerator for 30 minutes or until the coating sets. Optionally, use icing pens for additional decorations before serving.