Early and late summer tends to be nice, but this varies by year. In that time, the temperature will be perfect, and there will be no humidity. The city does have unpredictable stretches of heat between late June and early August when low 90s and high humidity are expected. All public transit options, including cabs, buses, and the subway system (called the "T") are air-conditioned.
Boston's fall foliage is at or near its peak beauty in mid-October, which also normally offers the advantage of many crisp sunny day (outside the city itself, peak foliage timing depends on how far north or south you venture from Boston.)
If you visit during the less busy wintertime, the Atlantic Ocean has a large moderating effect on temperatures. The average low in January is 22F/-5C, so as long as you dress appropriately, you should be fine.
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