Moravian Cemetery, the largest on Staten Island, was the ultimate winner. It's 274 years old, "often heralded as New York's most beautiful memorial site," and fairly close to the Grant City stop on the SIR. Moravian ended up completely exceeding all of my expectations and definitely shot straight to the top of my favorites list.
We spent about four hours walking through almost the entire cemetery and more than once I found myself saying "this cemetery has everything!" They had clean, convenient bathrooms when we needed them most, some of the oldest tombstones I've seen in the city (1770s), fascinating new (and incredibly gaudy) mausoleums and the largest concentration of ivy-covered tombstones I've ever seen in one place. I love, love, love a good ivy-covered anything but it adds a creep-factor to tombstones and cemeteries that is almost too much for me to handle.
Moravian has an amazing receiving tomb (beautifully labeled as such), a hillside mausoleum with incredible views of the water, the only headstone I've ever seen with the word "bones" on it, and some of the most beautiful fall foliage I've seen all year. East coast Octobers were positively made for afternoon cemetery strolls, and the day we went was perfect fall weather—sunny, yet chilly at the same time.
Moravian also gets the distinction of having the single most disturbing gravesite I've stumbled upon in my cemetery travels thus far. JMP pointed it out to me, and I don't think I'll ever be able to forget about five-year-old Harry B. Cairns—or stop wondering how he drowned, why someone felt the need to permanently etch that grisly fact on his headstone, why the 80-year-old grave looks so fresh, or who left that super creepy and tattered fairy doll behind.
And because I don't wish to leave you on that distressing note, I give you some of the other headstones that we came across at Moravian (although, unfortunately, not right next to each other):