It passed over the Swan Islands before moving ashore the Yucatán Peninsula on October 15 near the border between British Honduras and Mexico.

The hurricane restrengthened as it accelerated towards the U.S. Gulf Coast, reaching a peak with winds of 110 mph (180 km/h) shortly before making landfall near Pensacola, Florida, on the morning of October 18.

The resulting storm produced gusty winds over much of the Eastern United States and was blamed for the loss of 49 lives on Lake Erie in what became known as Black Friday.

The 1916 Pensacola hurricane arose from this broad area of low pressure, though its initial developments were not well-observed; a summary of the storm in the October 1916 issue of the Monthly Weather Review described its origins as "uncertain".

[1] The Jamaican Weather Service noted that it was difficult to differentiate the barometric influence of the developing tropical cyclone from the Virgin Islands hurricane.

[2] A reanalysis of the hurricane, conducted by the Atlantic Oceanographic and Meteorological Laboratory in 2008, determined that it began as a tropical depression east of Jamaica on October 9.

The hurricane maintained these winds for the remainder of its trek in the western Caribbean, eventually making landfall on the Yucatán Peninsula just north of the British Honduras–Mexico border on October 15.

The hurricane weakened as it traversed the Yucatán Peninsula and emerged into the Gulf of Mexico as a tropical storm by 12:00 UTC on October 16.

[3][4] As it was accelerating north towards the central U.S. Gulf Coast on October 18,[3] the hurricane's winds once again reached 110 mph (180 km/h), equivalent to a Category 2 on the modern Saffir–Simpson scale.

[1] The storm quickly weakened after moving inland, tracking over Alabama, Tennessee, Kentucky, and Illinois before ultimately merging with another area of low pressure near the Great Lakes by 12:00 UTC on October 19.

[3][4] This resulting combined system was initially broad and diffuse, but a dominant center of circulation soon emerged over Illinois on October 19.

[10] Beginning on October 14, the Weather Bureau began advising ships in the Gulf of Mexico of the storm's possible approach via the Yucatán Channel.

[11] Storm warnings were issued by the Weather Bureau for a stretch of the U.S. Gulf Coast between Bay St. Louis, Mississippi, and Carrabelle, Florida, on the morning of October 17.

[1] Hurricane warnings were issued for areas between New Orleans, Louisiana, and Apalachicola, Florida, on October 18 as the cyclone drew nearer.

[8]: 97  Rough seas along Santa Rosa Island and the Fairpoint Peninsula caused $10,000 in damage to railroads as embankments were eroded.

[3][nb 2] The anemometer in Pensacola was blown away a minute after recording the peak gust and shortly before the storm's eye passed overhead.

[30][31] Rainfall associated with the hurricane was heaviest farther away from the storm's center to the west and east,[1] with totals above 5 in (130 mm) across much of the Mississippi River Delta.

[32] Most rain occurred ahead of the system as it was approaching the coast, with drier conditions prevailing to the storm's south after it moved inland.

[1][8]: 98  Winds reaching 60–75 mph (97–121 km/h) on Lake Erie claimed the lives of 49 people and sank 4 ships in what became known as Black Friday.