We are just back from DS's overnight to USMA. For any parents that may decide to accompany their cadet, you may be interested to know how easy it was to go to NYC (we went overnight, but you could easily do a day trip.) Much depends on what you want to do at USMA -- there was a tour and parent briefing that we opted out of, mostly because we had toured before and DS has his appointment in hand already -- and/or how long you're going to stay in the area. You can take the Metro North train (Hudson Line) from either Garrison or Peekskill, both just about a 20-25 minute drive from USMA, and then it's a little over an hour train ride into Grand Central Terminal. Garrison station lets you park overnight -- my understanding of Peekskill station is that you cannot. Our round trips were around $30 each. Lots of fun was had and DS loved the overnight visit.