Beautful 360% views.
Incredible sunrise and sunsets.
Sunrise from the Lookout.
Naval Artillery Batteries
Built during WWII, these look posts were
manned by the Navy to watch for incoming German ships and
submarines (aka U-boots, or UnterSeeBoots)
"Wind" series of novels featuring
Cuttyhunk "resident" Kirsten
Eriksson.
OK, it's not strictly a "sight" per se, but
this series of 3 mystery novels with historical
overtones features a Cuttyhunk
Islander of Icelandic descent as one of the main characters.