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Castle on the Hill 

One of Ed Sheerans new songs released in January of 2017. Legend has it if you listen to it you can hear the crying of a million fangirls. Always equip tissues when listening to this masterpiece.
Ed saved 2017 with castle on the hill and I'm an emotional wreck.
Castle on the Hill by MemeFalcon January 7, 2017

The Fool on the Hill 

This definition painlessly stolen from Songfacts.
The Fool on the Hill:

Paul McCartney wrote this. It's about a man who is considered a fool by others, but whose foolish demeanor is actually an indication of wisdom. An event which prompted this song happened when Paul was walking his dog Martha, on Primrose Hill one morning. As he watched the sun rise, he noticed that Martha was missing. Paul turned around to look for his dog, and there a man stood, who appeared on the hill without making a sound. The gentleman was dressed respectably, in a belted raincoat. Paul knew this man had not been there seconds earlier as he had looked in that direction for Martha. Paul and the stranger exchanged a greeting, and this man then spoke of what a beautiful view it was from the top of this hill that overlooked London. Within a few seconds, Paul looked around again, and the man was gone. He had vanished as he had appeared. A friend of McCartney's, Alistair Taylor, was present with Paul during this strange incident, and wrote of this event in his book, Yesterday.

Both Paul and Alistair could not imagine what happened to this man. He had seemed to vanish in thin air. The nearest trees for cover were too far to reach by walking or running in a few seconds, and the crest of the hill was too far as well to reach in that short time. What made the experience even more mysterious, was that just before this man first appeared, Paul and Alistair were speaking to each other of the beauty they observed of the view towards London and the existence of God. Once back home, they spent the morning discussing what had happened, trying to make some sense of it. They both agreed that this was something others were infer occurred as a result of an "acid trip," but they both swore they had not taken or used any drugs. When Paul filmed the sequence for this song in the film, it shows him on a hilltop overlooking the town of Nice.

Harvard on the hill 

A nickname given to many community colleges in order to give students the sense that they are attending an institution comparable to Harvard in quality.

Many people believe that their college is uniquely nicknamed "Harvard on the hill", when in fact it is common of many community colleges.
Jeff: Where are you going to college?
Andy: Harvard on the hill!
Jeff: Woah congratulations, you're going to ABC Community College?
Andy: No? I'm going to XYZ Community College..
Jeff: Hm...
Harvard on the hill by PrimalHike February 28, 2015

the whorehouse on the hill 

The title given to a local high school in Hartsdale, NY. The school resides on a ridge (thus "on the hill") and is an all-girls Catholic high school. This title has been around for decades, and anyone who went to Catholic school in Westchester, NY is quite familiar with it.
Megan: Hey, where does that bitch goto high school now?
Lauren: Uhmmm I do believe she's at the whorehouse on the hill.
Megan: Figures, she's such a slut.

Harvard on the hill 

Typically of a Junior College; specifically of Moorpark College, in Moorpark, CA.
Bobken: So you going to Northridge next year.
Hidalgo: No, I'll probably go to Harvard on the hill.
Harvard on the hill by Peter April 15, 2004

The Fool on the Hill 

A Man all alone in life, mistaken and forlorn.

The Beatles created him and shhh...He's Paul...
The Fool on the Hill sees the sun going down, and the eyes in his head see the world spinning round.
The Fool on the Hill by Flower April 19, 2005