1. On August 16, 1777, the Battle of Bennington took place in Vermont, which greatly impacted the Revolutionary War efforts of Massachusetts. Massachusetts troops, led by General John Stark, played a pivotal role in the victory against the British forces.

2. In 1858, on August 16th, the East Boston Branch Railroad opened in Massachusetts, connecting Boston's East Boston neighborhood to downtown Boston. This railway played a crucial role in supporting the transportation needs of East Boston's growing population.

3. August 16, 1946, marked the opening of the Berkshire Theatre Festival, held annually in Stockbridge, Massachusetts. The festival has since become known for showcasing world-class performances, and is a notable cultural event for the region.

4. August 16, 1960, marked the birthdate of actor and comedian Steve Carell in Acton, Massachusetts. Carell went on to become hugely successful, starring in various television shows and movies such as "The Office" and "The 40-Year-Old Virgin."

5. On August 16, 2018, a gas explosion occurred in Lawrence, Massachusetts, affecting surrounding towns and causing significant damage to homes and businesses. This event led to the evacuation of thousands of people and fueled discussions regarding gas infrastructure safety in Massachusetts.