Complex sentence: The school awards varsity letters, blue with white trim, for both athletic and academic endeavors including music, choir, band, theater, debate, and chess--one per activity along with a pin and/or bar for years on varsity.
Split into simpler sentences: The school awards varsity letters for both athletic and academic endeavors, including music, choir, band, theater, debate, and chess. One letter is awarded per activity per individual, along with its corresponding pin and/or bar for years on varsity.