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The Loyalist refugees who made their way to Shelburne, Nova Scotia, in the aftermath of the American Revolution have been denigrated in various accounts as Loyalist “layabouts” and “dancing beggars” who spent too much of their time and capital on genteel sociability and conspicuous consumption. The writings of three of the sharpest critics of Shelburne—the Scottish merchant James Fraser, the Loyalist surveyor Benjamin Marston, and British Royal Engineer William Booth—often appear in modern academic works without sufficient contextualization. This paper asserts that the commentaries of Fraser, Marston, and Booth are not merely critiques of Shelburne per se, but part of a larger trans-Atlantic debate about the dilution and democratization of gentility. Indeed, the uprooted populations that made their way to Shelburne took advantage of the fluidity of the pioneer settlement to negotiate a form of middling gentility that acted as a vehicle of social mobility and identity reformation.