This is one of the longest hills in the state so it’s a required pilgrimage for any climber. The real beef of Skiff is in the first two miles so deploy your watts there. The ascent continues for another two miles onwards with several descents and pitches to the peak. There’s a great little pond just past the summit to rest and enjoy a celebratory cookie. What’s another random fact about Skiff you say? Near the summit there’s a fancy prep school whose mascot is a Pterodactyl. Badass!