Castleton preserves one of the finest early-nineteenth-century environments in Vermont. Settlers arrived beginning in 1767 from Salisbury, Connecticut, and by the onset of the Revolution, Castleton was a regionally important crossroads of the east–west trail through the Taconics and the north–south military road to Mount Independence. Prospering from milling and stagecoach commerce, the village developed parallel to the Castleton River along its stagecoach road, with an elongated green (that reads today as exceptionally deep setbacks on both sides of Main Street) bordered on the north by the meetinghouse and cemetery.
The village of Castleton achieved architectural prominence through the talents of its early-nineteenth-century joiners. The most noteworthy was Thomas R. Dake, who was born in 1785 in Windsor, where he appears to have been trained in the Connecticut Valley style of Asher Benjamin. Arriving in Castleton in 1807, he found employment with carpenter Jonathan Deming. By 1809 he had married Deming's daughter, built his own house (on South Street), and launched an independent career that would dominate fine construction in the village for at least the next three decades. Dake-built and Dake-inspired motifs abound within the village, from curving staircases to vaulted stair and entrance hall combinations, matchboarded facades, pilastered articulation, decorative friezes and lintel boards (many with Adamesque swags), blind semielliptical attic fans, and pedimented gable ends. The cumulative result is an important transmission of Benjamin's style across the Green Mountains.
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