The storm started quietly on the evening of the 26th of November, with a light but strengthening wind. Within hours it had grown to hurricane proportions and was creating havoc all along the coast. The winds raged all through the night of the 26th, all day on the 27th, and did not subside until the 28th, some 36 hours after the storm had started. Winds were clocked at up to 72 mph in Boston, and were probably even stronger along the coast southeast of Boston, especially on Cape Cod.

To call the damage widespread is a vast understatement. Houses were blown over and washed away all along the coast from Cape Cod to Portland, Maine. The coastline was littered with the wrecks and wreckage of dozens of vessels, large and small, smashed or sunk by the fierce winds and seas. In Provincetown harbor alone over 30 vessels were blown ashore or sunk. Damage along Boston's south shore and Cape Cod was probably the worst; telegraph lines were brought down, railways washed out, and even the low scrub trees of Cape Cod were blown away. In Scituate, a small coastal community 30 miles south of Boston, the coastline was permanently altered when mountainous waves cut a new inlet from the sea to the North River, closed the old river mouth, and reversed the flow of part of the river.

The steamer Portland at sea.

Portland departed Boston for the final time at 7 PM on November 26, 1898, crowded with passengers returning home after the Thangsgiving holiday. At the time of her departure the weather was worsening, but had not yet deteriorated to the point that sailing was deemed inadvisable. As she steamed northeast towards Portland, however, conditions quickly worsened. At 9:30 PM she was sighted passing Thatcher's Island, a short distance northeast of Boston, her progress clearly hampered by the deteriorating weather. Although she was still making headway against the storm at this sighting, she probably did not get far before her progress was stopped.

Between 11 and 11:45 PM Portland was sighted three times, but this time to the southeast of Thatcher's Island - she was being driven south by the storm. When sighted at 11:45 PM, she is said to have shown severe storm damage, especially to the superstructure. By this time conditions on the steamer must have been dreadful, and all aboard must have known they were in grave danger. Unable to make progress against the storm and unable to make for safe port, Portland's only hope lay in working her way offshore and riding out the storm at sea. Her attempts to reach the open sea accounted for her slow movement to the east between the 9:30 and 11:45 sightings.

At 5:45 AM the following morning, lifesavers on Cape Cod heard four blasts of a steamer's whistle. It is now believed the whistle was that of the doomed Portland. In the course of the night the storm had driven her even further backwards, so she was now far southeast of Boston. Between 9:00 and 10:30 that morning the eye of the storm passed over, and several persons claim to have seen Portland wallowing five to eight miles offshore, clearly in great peril. No further sightings were made that day, as the storm closed in once again.

At 7:30 that night, more than 24 hours after Portland had sailed, a lifesaver on his regular beach patrol found one of the steamer's lifebelts washed up on the beach. Fifteen minutes later several fourty-quart dairy cans were found in the surf. At 9:30 doors and woodwoork from Portland were found. Around 11:00 the rising tide brought in massive quantities of wreckage, giving clear evidence that Portland had been lost. It is said that this tragic news was communicated to the world via a bizarre relay - by telegraph across the trans-Atlantic cable to France, then to New York via another undersea cable, and from there on to Boston - for the telegraph cables between Cape Cod and Boston had been blown away by the storm.

All those aboard Portland, believed to be a total of 191 passengers and crew (the only passenger list was lost with the ship), were killed. Eventually 36 bodies were recovered along the beaches.

Many of the bodies wore wristwatches that had stopped at 9:15. It is unclear, however, if this indicates the ship was lost at 9:15 AM, or at 9:15 PM. Although there are several reports of the ship being sighted, afloat, between 9 AM and 10:30 AM that day, the exact times of those sightings are not known. If any of those sightings took place after 9:15 AM, then the ship must have survived until 9:15 PM that day, some 26 hours and 15 minutes after she had started her doomed voyage. However, Portland would not have carried enough fuel to remain at sea, in storm conditions, for over 24 hours. She could have burned furnishings, interior bulkheads, and other wooden materials to keep the boilers running, but the quantity of this material washed ashore tends to indicate this action was not taken. Also, it is highly questionable whether she could have held together for 24 hours, given the terrible sea conditions. Still, the fact that major debris did not begin to wash ashore until 9:30 PM suggests that Portland had survived into the night - surely, if she had been wrecked at 9:15 AM, debris would have been washed ashore in the morning. Because the exact time of the final sightings cannot be firmly established, it is impossible to conclusively determine the exact time of Portland's loss - either 9:15 AM, or 9:15 PM, on Sunday, November 27, 1898.

Portland's remains were eventually located on the seafloor about seven miles offshore, and have since been explored. The small schooner Addie E. Snow was also lost during the storm, and her remains lie less than 1/4 mile from Portland's grave. It is thought that the two vessels may have collided, hastening their ends.