It can get very pricey the first year. If I were to rank the importance of "must be there" events it would be;
A-Day - Family Event
You have the weekend with a very tired Plebe
PPW- 1. Parents 2. Family Event
The Plebes are given two tickets for the dinner, space is very limited
Great being with your Plebe the weekend
R-Day- Plebe drop off in the morning, thats it no personal contact till A-Day
Push Hard, Press Forward
I would agree with Tug's assessment overall.
R-Day: It is a unique experience that you and your CC will share and remember forever. Emotional time with the added shock of feeling like you have fallen into a cold pond unexpectedly. There are things to see and do all day long and concludes with a formation and the CC repeating their oath on the Plain. Our CC had high stress which we could observe grow as we got closer to WP. By R-Day morning he was on pins and needles and would barely speak to us. Some CC don't want their parents there and I would acquiesce to their desire (but push to go).
A-Day: a very proud event that helps make up for the six weeks of no/limited contact. You need to be there for your cadet as they need to get off of base after enduring CBT. It is their only chance for some normal experiences (dinner out; movie; time with family and friends) before Christmas break, as there are limited things to do around WP within their normal walking privileges. Encourage extended family to come. If it is feasible, get there early enough on the Monday of ReOrgy week to watch March Back.
PPW: From a parent's perspective, if I could only go to "one event" it would be PPW - which happens the weekend before Spring Break and is the major annual Plebe event. Plebes are released for Spring Break on Sunday morning. Most upperclassman are gone by this time, and the Plebes are somewhat relaxed. As a parent, your only chance over four years to see the barracks, tour the uniform factory, and see anything and everything related to West Point (that you can squeeze in; we told our DS that eventually he needs to become commandant as we could not get a place on the tour of the commandant's quarters, so we have not yet seen them). You can learn more about WP overall in those two days than you could in a lifetime from touring and visiting.
Tug is correct: it can be very pricey to travel and stay near WP for these events. But all of these give exactly
one opportunity to experience them. For those who are in the NE, you are fortunate. For those on the Left Coast, you have my sympathy. Fortunately WP Parents understand that not all parents can attend everything so there are always people volunteering to take and host your cadets should you not be able to be there for things like A-Day.