@TheOtherMaven

I was speaking of the more contemporary meaning
used by the boating community between the cape and islands

since the whales are almost gone now

From Ptown ..

“When you drive up the Cape and go to the point—all the other stuff has left you. By the end of the drive, you are someone different. You’re in a totally free environment.”

~

#1.1.1
Per Wikipoo: "A Nantucket sleighride is the dragging of a whaleboat by a harpooned whale while whaling. It is an archaic term from the early days of open-boat whaling, when the animals were harpooned from small open boats. Once harpooned, the whale, in pain from its wound, attempts to flee, but the rope attached to the harpoon drags the whalers' boat along with it."

That's what I thought I remembered. (Nantucket was the center of the US (and world) whaling industry circa 1750-1850, until overtaken by New Bedford on the Massachusetts mainland.)

Whaling was based on greed (for the lucrative resource of whale oil, a virtual necessity until it in turn was replaced by petroleum products starting in the late 1840s), savagery (hunting and killing whales), and ignorance (because no one realized that whales, like all the cetaceans, were intelligent beings).