I happened to talk to the HC for 30 minutes at Headfirst this week. Casual conversation, not about my son as he is on a different path. Turns out we grew up near each other in Ohio and played college sports around the same time, so mostly that type of talk.
I thought he was a great guy. He has been HC at Kenyon for 22 years, though he hasn't turned 50 yet. He was the youngest HC in D3 when he was named HC at Kenyon. He said he has raised his family in Kenyon and he has loved living and coaching there.
This was not "coach/recruiting speak", this was just 2 guys with similar backgrounds casually talking about life and Ohio. He played college baseball at another school in their league, and he has a daughter who is playing a college sport at another school in the league. So one would have to assume there isn't anything he doesn't know about the area and league!
We didn't talk much baseball, more about Kenyon, D3 and Ohio. There are some great D3 colleges and sports programs in the upper Midwest, just like New England. Kenyon is known as one of the better academic colleges among those types of schools in the Midwest. They get a lot of students from the Northeast as well, if that impacts your thinking.
Obviously depending upon what your son wants to study and what he may want to do after college, Kenyon is one of those schools that very likely can help your son "get there from here". And the coaches and players in that conference and area really get after it competitively, so the college sports experience would be available as well if that's what your son wants.
One last thought -- as I recall from my playing days in that conference, Kenyon is pretty centrally located, so most of the van rides to away games are probably only 1-3 hours. Helps cut down on time away from studies.
Good luck!