The Wesleyan "authorities" (e.g., Public Safety or "P-Safe") are very lax in their enforcement of school rules/the law. On any given day, you will see multiple people sitting on Foss Hill smoking weed, sometimes out of conspicuously large bongs, and they will not get "busted." However, if you are stupid and do something right in front of the Po-Po, they might get you in trouble. Getting in "trouble" ranges from getting a warning to getting SJB'd (sent in front of the Student Judicial Board), which could result in another warning, writing a paper/apology letter, community service hours, or more serious punishments, depending on what you did wrong. There is very little crime committed by Wes kids other than underage drinking and drug use, some vandalism (art), and public nudity. Fire safety inspections happen in residences randomly, but they are not allowed to open drawers, so as long as you don't leave illegal things out in the open, you will be fine.
Interaction with the Middletown Police is strained, after an incident where they broke up a party using unnecessary force. However, students mostly only interact with P-Safe officers, and the Middletown Police only come when there is an emergency or a particularly rowdy party.