While researching the origins of the Ulster & Delaware Railroad (first named the Rondout and Oswego and then the New York, Kingston and Syracuse), Burr Hubbell came across a description of the line from Kingston to Roxbury in the July 4, 1872 Kingston Freeman. It includes tidbits about the hamlets served by the railroad, including Halcottsville (then spelled without the ‘s’) and the valley known today as Bragg Hollow.
“Brag Hollow came by its name in a way that might interest those who like fresh bits of history. In this hollow lived the Hewetts, Hubbles, Boutons and Kellys. The people around the country used to have entertainments called logging bees. At these bees they would bring their oxen, and see which team could pull the biggest log. The folks who lived in the hollow didn’t have such wonderfully good oxen, but they made it up in bragging of their merits, and won many a game by this small gift. That place then began to be called Brag Hollow, and has been called so ever since.”
Another version of this story says it was the height of the corn the local farmers bragged about. Why a second ‘g’ was added, or when the name was changed from Peaceful Valley (as it is on the 1869 Beers Atlas) remains a mystery.