All In The Family
Instead of carving jack-o'-lanterns or little glowing monsters, trade your pumpkin stencils for the family portrait. Have each member of the family carve (or paint, depending on ages and carving comfort levels) a pumpkin version of him or herself, and be sure to allow for interpretation!
While pumpkin hunting, have each family member to choose a pumpkin that most resembles themselves. Alternatively, choose them by size of each family member: small for the little ones, medium for teens and large pumpkins for adults.
When it's time to decorate, keep not only carving tools and paints on hand but other crafty accessories such as plastic glasses, cotton or yarn for hair and maybe a tie for dad.