Maine’s largest city has burned down quite a bit.

Fire has even been inspiration for those of you entering our Portland flag contest. Many design submissions have featured a phoenix, which is a mythological bird that rose from its ashes to live again.

The phoenix is a pretty apt symbol for a city that has continually remade itself after fire. So we went looking for pictures of the former iterations of Portland — the city that kept rising from the ashes.

You’ve probably heard of the July 4, 1866 fire — apparently started by fireworks and dry temperatures. It began on the waterfront and burned through the area where most people lived and worked, destroying 1,500 buildings and leaving 10,000 people homeless.

People described it as the worst fire of its kind in an American city up to that point.

Portland installed a fire alarm signal system in 1867, to prevent a similar tragedy from happening again. And the mayor in 1868 signed a contract to pipe in water from Sebago Lake to increase the city’s water supply, according to the Maine Historical Society.

But extra water doesn’t matter if the fire alarm doesn’t work.

Portland City Hall on Congress Street, which burned in the 1866 fire, was equally unlucky again, in 1908. That year, historians believe a fire started in the electrical wiring in the fire alarm room, located on the third floor of the building.

Unfortunately the fire destroyed the city’s fire alarm, meaning the firefighters at the station right across the street didn’t know about the fire until it was too late.

Here is city hall before the fire, in 1904:

And here it is after the fire, sometime between 1910 and 1920:

The area we know as Portland today was also destroyed during King Philip’s War in 1676 and again in 1775 by the British.