Head of the Charles Regatta, Boston
The title would have been accurate about 230 years earlier. Now you can take a sailing class at the community boathouse, or rent a canoe/kayak to paddle along the Charles. Past Harvard, the scenic wooded banks of the river give no trace that you're in the middle of the city! If you're feeling competitive, you can try your hands at racing the collegiate scullers who are flying up and down the river.
The public sailing pavilion is on Storrow Drive near the foot of Longfellow Bridge. The canoe rental pavilion is in a park on Storrow/Soldier's Field Road a little past Harvard stadium.
This regatta takes place at the end of october on St Charles River and attracts huge crowds that cheer the different college crew teams that came here to compete.