From Thursday, June 10th, to Sunday the 13th in 1999, less than a month before my 22nd birthday, I took my first trip to New York with a group out of University of Wisconsin in Madison. I remember the group stayed at the Mayflower Hotel at Central Park (which is now gone and torn down). During the trip, we saw The Lion King (officially my first Broadway show), the Death of a Salesman revival with Brian Dennehy and Amy's View starring Judi Dench. Had a great time, met up with some friends who were in the local area, and fell in love with the city.
I took the same group trip a few years later in February 2002 (mainly to see the original cast of The Producers), but I spent most of my time by myself on that trip. That's what started my personal theater trips, where I came out by myself and saw as many shows as possible. Became an annual event, and eventually a twice a year event that lives on today.