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Although dated in some respects, Charles Homer Haskins’s The Renaissance of the Twelfth Century is the classic that did much to convince people that the Middle Ages weren’t “Dark.” Haskins’s The Rise of Universities is also valuable.
Robert Rait’s classic essay Life in the Medieval University is available in a free Kindle edition (or in print).
The concept of the trivium is the foundation of the classical Christian school movement in the twenty-first century and is also employed in many parochial schools. Sister Miriam Joseph’s The Trivium explains modern applications of this medieval model.
Josef Pieper’s Scholasticism is a good introduction to scholastic philosophy.
Abelard’s Historia Calamitatum
St. Thomas Aquinas’s Summa Theologica. If you would prefer a slimmed-down version of this long work, try Peter Kreeft’s abridgment, A Summa of the Summa.

Universities and Scholastic Philosophy – Quiz

List the components of the trivium.
List the “three professions” recognized in the medieval world.
St. Thomas Aquinas’s most important work is his textbook titled _____________.
The University of __________, which specialized in law, is usually given credit for being the oldest university in Europe.
The chief goal of the scholastic philosophy was to reconcile _________ and __________.
The syllogism is an example of __________ reasoning.
True/False: At some medieval universities, students organized the curriculum and hired professors to teach them.
____________ is known for his ontological proof of the existence of God.

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