A stubborn five-alarm fire blazed last night through three commercial buildings in the historic district of Annapolis, near the State House and the Naval Academy.

About 75 firefighters fought the fire for hours in cramped and hazardous conditions in the 100 block of Main Street as scores of people gathered in the cold to watch leaping flames and clouds of gray and white smoke billow upward.

Damage was described as "very, very, very substantial" by Harvey Blonder, who said he was one of the owners of the structures. "I believe it's a total wipeout," he said.

The fire broke out shortly before 8 p.m. in one of the two- and three-story buildings about 300 yards east of the State House.

Capt. Joseph Martin of the Annapolis Fire Department said the blaze was declared under control at 11:42 p.m.

Firefighting difficulties abounded. Buildings were close together, surrounded by narrow old streets. Authorities said the buildings' upper floors lacked sprinklers. At one point firefighters were called out of one of them when "the roof got weak," Martin said.

The fate of the structures was uncertain early today: "You might have a great big hole," Martin said.

Martin said the blaze was originally reported as an electrical fire on or near the ground floor of the building that houses the Candy Factory, at 118 Main St. But he said it was too early to know the cause of the fire.

He said it spread to an adjacent building that houses a jewelry store and to one next door to that, which houses an ice cream shop.

One firefighter suffered a minor injury, when embers fell down his back, Martin said. No other injuries were reported.

He said the jewelry store was open at the time the fire began. He believed the businesses in the other two buildings were open as well. Authorities said power was cut off to fight the fire, prompting the evacuation of other businesses. They said WRNR (103.1-FM) , based nearby, went off the air.

On arriving at the scene, Michael Fox, who was acting as Annapolis mayor last night, said, "There were flames coming off the roof, there were flames shooting out the windows" before everything turned to smoke.

Witnesses reported hearing the crash of glass breaking as firefighters smashed windows. They told of feeling the spray from streams of water from hoses and an aerial tower, and they described the orange flames reflected in the windows of nearby buildings.

Of the buildings that were ablaze last night, "at least two of the three are significant historically," Annapolis architectural historian Orlando Ridout said.

Ridout said he believed two of the buildings might date to the 19th century, one to the middle of that century. Blonder, the owner, said he believed they were built in the 1920s.

Officials said the three buildings were wood frame structures, two of them brick facades. The facade of the jewelry store appeared relatively recent.

Officials said the use of the buildings' upper stories was confined to storage due to the lack of sprinklers.

That lack is "one of the problems of these empty-second-story buildings," said City Administrator Robert D. Agee. He said a program had been initiated to make possible sprinkler installation in such older structures.

Patrick McLean, a night ice cream scooper at a Ben & Jerry's nearby, said he could see the tips of the flames "coming off the roof" of one of the buildings.

"It's sad," said Laura Strachan, a neighborhood resident, referring to the damage to the old structures.

When she first went to the scene, she said, she saw smoke streaming from windows on an upper floor of one building, which a witness described as a three-story structure with a red brick front.

The ice cream store building appeared to be three stories, with a red tin roof and three gables.

Throughout the night, smoke appeared to be illuminated from within by the glow of flames and from firefighters' spotlights.

It rolled down the slope toward the harbor, no more than 100 yards or so from the scene.

Firefighters responded from the Naval Academy, Anne Arundel County and Fort Meade as well as Annapolis, Martin said.

Staff writers Joshua Partlow and Martin Weil contributed to this report.

Crowds gather along Main Street in Annapolis to watch firefighters battle a blaze that spread through three buildings in the historic district. Fire crews battle the Annapolis blaze, which began about 8 p.m. and continued into the night. About 75 firefighters responded.Firefighters battle the blaze on Main Street in historic downtown Annapolis. The cause of the blaze is under investigation. One firefighter was injured.