Photo: Igoe Meijer

The largest annual event of its kind in the world, the 55th Head of the Charles Regatta graces the waters and shores of the Charles River October 19 & 20. Featuring top rowers from across the globe, this venerable competition also attracts thousands of fans, who flock to cheer on the racers and mingle with fellow aficionados at the Rowing & Fitness Expo, Reunion Village and Weld Exhibition near Harvard Square, which offers food vendors and official Regatta merchandise.