Cut half the red pepper into thin strips, then take each strip and cut into 4 small pieces for the legs. Take the other half and make 4 small circles for the heads with a small round cookie cutter.
Peel the cucumber and cut into slices.
Layer the cucumber slices in a caterpillar wiggle across a plate. Add red pepper circle for the head, add the slices of peppers for the feet. Use small leftover pieces for the eyes and antennae.
Serve with ranch dressing for dipping.