This prominent brick block overlooking the village green preserves the character of Federal-styled commercial Middlebury. Its site, adjacent to that of the first county courthouse, was occupied by a tavern beginning in the 1790s. After fire destroyed the tavern it was reconstructed as a major stagecoach hotel, which reflected the town's booming economy in the marble and textile industries, at a strategic junction of stagecoach roads to Boston, Montreal, and Troy. The inn's basic vocabulary reflected high-quality contemporary domestic construction in the region—brick, trapezoidal marble lintels, and a sidelit door with semielliptical fanlight and pilasters with elliptical sunbursts on the N. Pleasant Street side. The inn's size, at three-and-a-half stories and fifty rooms, and its grandeur—a coved-ceiling ballroom—also spoke of urbanity and ambition. Since its opening as the Vermont Hotel, it has changed names twice, lost its octagonal cupola, variously gained and lost Greek Revival porticoes and Stick Style and Queen Anne verandas, gained a gabled addition facing Court Square in 1897, and received a major Colonial Revival remodeling in 1927. This last removed mid-nineteenth-century paint from the brickwork, imposed a gable-end parapet and a new main entrance, and reworked the public spaces on the main floor. But it also preserved the original shell of the inn, which is now a rare survivor of a building type that has largely disappeared from American townscapes through fire and redevelopment.