If you take Mark's first rule for the "tallest building north of Boston" and extend the boundary just 22 miles to the west of New England, the Erastus Corning Tower at 589 feet in Albany wins the title. It is also the tallest building in the state outside of NYC which includes Buffalo, Rochester and Syracuse. In addition, seeing that Cleveland is located south of Boston, Albany's skyscraper would be the tallest between Boston and all the way to Detroit as you head west while still remaining north of Beantown. I respectfully request a 22 mile waver from markhb in order to claim my prize!
Toronto would win hands down if you included Canada when going between Detroit and Boston. Otherwise you are correct about Albany's within the states. The tower actually sits in an even more awesomely dystopian plaza than Boston's City Hall, with a sibling of City Hall within that plaza!