5 signature festivals and events in Boston

This annual festival in mid-August in the North End honors the Madonna del Soccorso (Our Lady of Help) from Sicily. Since 1910, it has celebrated the city’s Italian immigrant heritage with religious processions, Italian food, and music. The highlight, the ‘Flight of the Angel’, features local children performing the angelic descent from historic buildings, culminating in a vibrant street celebration.

The Head of the Charles Regatta, held annually in late October on the Charles River, is the world’s largest rowing event. Spanning three days in October, it showcases elite rowers from around the globe. The three-mile (five-kilometer) course, flanked by enthusiastic spectators, offers thrilling races and an upbeat festival atmosphere, celebrating rowing and autumn in Boston.

Held each summer in Boston Common, typically between mid-July and August, this free event presents a different Shakespeare play annually. The performances, set in an open-air theater, invite audiences to enjoy classic works in a communal and accessible setting. This tradition continues to be a cherished part of Boston’s cultural scene, celebrating Shakespeare’s legacy with exemplary outdoor theater.

South Boston St. Patrick’s Day Parade, held annually on the Sunday closest to March 17th, celebrates both Irish heritage and Evacuation Day. Crowds dressed in green cheer on bands, floats, dancers, and military units along the parade path. Originating in 1737, it honors Ireland’s Patron Saint, as well as the city’s historic military achievements.

Serving as one of the U.S.’s largest Fourth of July festivals, Boston Harborfest highlights Boston’s maritime and revolutionary history. Celebrated with historical reenactments, a Declaration of Independence reading, and a stunning fireworks display over the harbor, it commemorates America’s independence and Boston’s central role in shaping it.