Both outbursts of violence happened just after 2 a.m., closing time.
Customers spilled out of bars and nightclubs on King and Ann streets in downtown Charleston.
In the first episode last month, a man milling outside one of the clubs attacked a transgender woman in what advocates labeled a hate crime, police said.
Then early on Labor Day, someone thought to have just left a club started shooting, sending bullets into windows and hitting a police car near an officer overseeing the exodus of revelers.
Citing the recent violence, Charleston police plan to increase patrols in the area that has seen a surge in activity with the addition of new businesses over the past year, they said Tuesday.
Lt. Heath King, who commands the Charleston Police Department's efforts in the city's central business district, said he hopes the measure will "root out any problems ... and generally make people feel safe."
"We want people to have a good time," he said. "But we have to address disorderly behavior before ... it becomes a problem."
Charleston officials have sought in recent years to temper crime fueled by late-night crowds of the Upper King Street corridor. Vandalism and fights have been blamed on drunken patrons.
But on weekend nights, King said, about 16 officers now will patrol the area and look for trouble before it gets out of hand. On Thursdays, when college students tend to frequent the bars, about 14 officers will be on duty there, he said.
Upper King Street is a popular destination for diners and bar-hoppers. But Ann Street, which links King and Meeting streets, has become home to several bars: Dudley's On Ann, Music Farm, The Brick, Deco Nightclub. Two of them opened since the start of 2017.
"Some of the side streets are starting to become heavily patronized," King said. "It puts large crowds of people into areas where they haven't been before."
The street also is home to one of the largest parking options in the district: the Charleston Visitor Center garage.
On Aug. 19, a 34-year-old Goose Creek woman was walking to the garage from King Street bars when she encountered a man near Deco Nightclub. The man used slurs about her gender identity and punched the woman, knocking her out, detectives said. Christopher Lamar Price, 30, was arrested Tuesday in connection with the assault.
King said video footage showed a suspect outside Deco, talking with an employee there, before the attack.
In the most recent incident early Monday, the burst of gunfire sent terrified people scattering on Ann Street. An officer was standing outside his cruiser when a bullet hit the car. Another round struck a civilian vehicle. Another pierced a window at the parking garage.
Investigators later found 14 shell casings.
Witnesses told the police that the shooter, who has not been identified publicly, had been at Deco that night.
While King said he planned to meet with Deco's owner, the club's lawyer disputed the police accounts of both episodes, saying video footage indicated no connections between the business and the suspects in either case.
Attorney David Aylor argued that Deco, which opened in a building once occupied by Club Pantheon, has been unfairly labeled as a source of violence because of its proximity to a parking garage used by people frequenting the area's many bars and restaurants.
The club's operators welcome the increased police presence, Aylor said.
"That's something that Deco wanted from the beginning," he said. "They just want to have a good club."