A man holds a sign outside the Harvard Square T-stop offering a “Free Bible Quiz.”

Bruce M. Benson says his objective is not to convert people, but to start conversations with the people he encounters in the Square.

And the Pit, the sunken amphitheater that surrounds the T-stop entrance, seemed the perfect place for interesting encounters.

In the 1960s, he might have run into Bob Dylan or Joan Baez. But in the past twenty years, the Pit has been host to some less glamorous appearances.

Benson, who has lived in Cambridge for 18 years, recalls that in the early 1990s the Pit drew some unsavory characters.

“It was a free–for–all, open air mental institution,” he says.

In the past decade, Cambridge residents have raised concerns about violence and drug use among some frequenters of the Pit.

Still, store owners in Harvard Square say that the vibrance of the Pit is good for business: it sets the Square apart from the rest of Cambridge.

A HISTORY OF VIOLENCE

“Some people are uncomfortable of the gatherings of people there,” says Fred Berman, a planner for the Cambridge Department of Human Services.

“Rough characters” as well as the “transactions that happen outside the law” are a point of concern for some residents, he added.

In September 2000, three undergraduates were attacked by seven people they labeled “intoxicated skinheads,”—allegedly from the Pit—on Mt. Auburn St. The next day, a Muslim undergraduate was attacked on Bow St. as he walked back to his dorm from evening prayers in Canaday. His attackers were also later identified as skinheads who hung out in the Pit. Many in the Harvard community viewed the attack as a hate crime; the Harvard United Ministry organized a silent vigil at Memorial Church, followed by a peace march through the Pit.

But the violence didn’t end there.

In 2001 Io Nachtwey, a homeless woman who hung out at the Pit, was stabbed to death and thrown in the Charles by a gang-like organization from Boston that had recently begun to frequent the Pit.

Finally, in June 2003, three teenagers known to have spent time in the Pit were arrested after stabbing a man in front of Pizzeria Uno.