This lecture will unpack the lay sermon delivered by John Winthrop in 1630 as the first ships in the great Puritan migration from England neared the shores of Massachusetts. The sermon is remembered most for its peroration – “we shall be as a city upon a hill” – which still informs the American Thanksgiving holiday. The interest for a Pusey audience lies in how Winthrop defined Christian Charity and adapted this to the work of building a community in New England. Some aspects of the sermon still resonate – “we must be knit together in this work as one man…we must uphold a familiar commerce together in all meekness, gentleness, patience and liberality.” In other ways Winthrop’s acute analysis of factors that might lead Puritans away from second commandment duties is of its time and unfamiliar. The lecture, and discussion following it, will branch out from the sermon itself to look at how Winthrop’s vision played itself out on the ground. A theme of the recollection is the peculiarity of the Puritans’ covenant theology and their interest in the then novel concept of a covenant of grace.