Benjamin exhibited an aptitude for architecture by carving Ionic capitals for the 1794 modifications to the Oliver Phelps House at Suffield, Connecticut.

The latter's use of overall symmetry, blind arches, fanlights and smooth brick greatly influenced Benjamin, who popularized the urbane Federal style in countryside estates.

Robert Henry Eddy, Elias Carter, Solomon Willard, Samuel Shepherd and Ithiel Town are credited among his pupils.

He adapted many designs by James Gibbs and Colen Campbell of Great Britain to fit the scale and finances of New England communities.

These handbooks provided superb drawings and practical advice for full house plans, including such details as circular staircases, doorways, fireplace mantels, dormer windows, pilasters, balusters and fences.

In fact, his book published in 1830, The Architect, or, Practical House Carpenter, helped redirect American taste towards the Greek Revival movement.