Given a 5-peg by 5-peg geoboard, how many different lengths can be made by stretching a rubber band to form an oblique segment between any two pegs? This investigation requires students to make connections to the Pythagorean theorem, congruence, and combinations. With its use of visual representation and a range of mathematical ideas that can be explored from simple to complex, this task makes meaningful mathematical investigations accessible to learners with varied levels of prior knowledge. (Contains 4 tables, 3 figures, and a classroom activity sheet.)