The South Shore of Massachusetts is a geographic region stretching south and east from Boston along the shore of Massachusetts Bay toward Cape Cod. Communities of the South Shore include:

Boston is the largest city, located at the innermost point of Massachusetts Bay, at the mouth of the Charles River, the longest river entirely within Massachusetts. Most of the population of the Boston metropolitan area (approximately 5,800,000) does not live in the city; eastern Massachusetts on the whole is fairly densely populated and largely suburban.