Activists from both sides of Annapolis's long and bitter debate over an anti-loitering law are now awaiting the city's first "loitering free" zone, but for different reasons.

On one side are Eastport residents who are the first to apply for a neighborhood "loitering free" designation, a new law enforcement tool intended to crack down on open-air drug markets.

On the other side are civil libertarians, who are waiting for city officials to approve the application--so they can start fighting it in court as an assault upon essential human rights.

Last week, just several days after the Annapolis City Council narrowly approved the new law, the Eastport Watch Group became the first organization to seek the zone status, which would allow police to order known drug offenders to stop lingering in public places.

"We feel we need to do something," said John L. Elliott, a block captain for the group and longtime resident who is troubled by the corner drug deals and prostitution he said he sees around his block.

The American Civil Liberties Union of Maryland claims the zones would wrongly criminalize constitutionally protected rights and would open citizens to harassment by police. ACLU attorney Dwight Sullivan said the group will file suit as soon as the council creates the first "loitering free" zone.

After months of heated debate over a bill that prompted protest marches and threats to recall the alderman who introduced it, the council passed the bill Oct. 11 with a tie-breaking vote by the mayor.

The new law allows the city to create no-loiter zones, at the request of neighborhood associations or individual residents, if the area has had at least three drug arrests within the past two years.

Police would then have the authority to order anyone convicted of a drug offense in the last seven years to leave the area if they were seen hanging around, as well as anyone the police had reason to suspect was dealing drugs.

Those asked to leave who failed to do so could be charged with a misdemeanor.

Supporters argued that the law was necessary because city police were otherwise unable to break up groups of people involved in suspicious transactions in the open on private property, such as the city's public housing complexes.

But opponents--including many black activists--complain that the law would restrict personal freedoms and give police license to unfairly harass black residents.

They point to a recent U.S. Supreme Court ruling that deemed unconstitutional a Chicago ordinance allowing police to arrest suspected gang members found loitering in public places.

But defenders of the Annapolis bill said it was legally sound because it specifies particular neighborhoods.

City officials said the Eastport Watch Group's application will be reviewed by police. If police confirm that the neighborhood meets the criteria, the application would be voted on by the council, possibly at its Nov. 8 meeting.

Sullivan said that although the ACLU could sue now, "the city would make the argument that it isn't yet interfering with anyone's constitutional rights."

But the ACLU won't wait for the police to start enforcing it either. Sullivan said that just declaring the neighborhood a zone would violate some people's rights by making it illegal to participate in First Amendment-protected activities, such as speaking to someone in a parked car.

"The Annapolis City Council intends to let police determine who's a 'good' loiterer and who's a 'bad' loiterer," Sullivan said. "It invites police to make standardless distinctions between people standing on street corners."

Antonio Brown, a Bywater resident who supports the bill, said it is necessary to end what he describes as flagrant drug dealing and violence in Annapolis neighborhoods.

But while he believes that many of his neighbors agree, he doubts that any would take the initiative to apply for the zone status.

"A lot of people are supportive of the bill, but they don't want to be outcasts for speaking up," said Brown, who describes himself as a longtime activist for civil rights.

He denies that innocent people would be the victims when police started enforcing the law.

"We don't have groups of people hanging out on corners of our neighborhood that are talking about how work went today or how to revamp the playgrounds for kids," he said.

"These people who hang out in the neighborhoods are involved in the [drug] trade. . . . I don't believe a law like this infringes on their rights."