Though it was initially believed the storm struck Haiti, where considerable damage was reported along the coastline near Port-au-Prince, and ultimately deteriorated, modern reanalysis suggests the cyclone continued south of the island.

[6] The newly formed system intensified on a west-northwest course parallel to the Bahamas, attaining hurricane strength by 00:00 UTC on August 1.

The system weakened as it progressed through the Mid-Atlantic and into the northwestern Atlantic, and it was last considered a tropical depression around 06:00 UTC on August 4 about 105 mi (169 km) east of Nantucket.

[2] Despite the storm's small size, it produced wind gusts of 72 mph (116 km/h) in Wilmington, North Carolina, where the hurricane unroofed many houses, felled communication lines, shattered glass windows, and uprooted hundreds of trees.

On a west-northwest course, the system organized into the season's first Category 3 major hurricane around 12:00 UTC on August 19, attaining peak winds of 120 mph (190 km/h) six hours later.

The cyclone entered the Bay of Campeche as a strong tropical storm weakened to sustained winds of 40 mph (64 km/h) before moving ashore just north of Tecolutla, Veracruz.

Across Jamaica, numerous buildings were heavily damaged, including light-frame dwellings that were blown down or crushed under fallen trees.

[10] Trekking through the Caribbean Sea, the system coalesced into a tropical depression about 115 mi (185 km) east of the Isla de Cozumel by 12:00 UTC on August 18.

The system moved ashore northeast of San Fernando, Tamaulipas, with slightly weaker winds of 50 mph (80 km/h) before progressing inland and dissipating by 06:00 UTC on August 23.

[12] On September 8, a weak area of low pressure developed along the tail-end of a stationary front across the northern Gulf of Mexico.

The fledgling system moved north and then northeast, making its first landfall along the Mississippi River Delta with peak winds of 65 mph (105 km/h) around 19:00 UTC on September 10.

[2] That day, the crew of the USS Alacrity near the hurricane – then centered northeast of the Bahamas – observed a barometric pressure of 918 mbar (27.1 inHg), the lowest in association to the storm.

The cyclone weakened further to a Category 2 prior to making landfall near East Hampton, New York, around 02:00 UTC on September 15 and near Charlestown, Rhode Island, about two hours later.

After emerging into the Bay of Campeche early on September 21, it re-attained peak winds of 80 mph (130 km/h) and made a second landfall near Paraíso, Tabasco.

[6] The ninth storm of the season formed early on September 21, via a tropical wave that departed the western coast of Africa several days prior.

After reaching its peak as a Category 2 hurricane with maximum sustained winds of 100 mph (160 km/h) around 12:00 UTC the next day, an approaching cold front prompted the beginning of extratropical transition.

[2] On September 28, a broad area of low pressure developed adjacent to a dissipating warm front over the north-central Atlantic.

[10] The cyclone congealed over the next two days and attained tropical storm status by 00:00 UTC on September 30,[2] which was confirmed by a nearby ship report.

The system weakened to a tropical depression the following day and was subsequently absorbed by an approaching extratropical cyclone by 00:00 UTC on October 3.

[2] The eleventh tropical storm of the season was first detected about 80 mi (130 km) north of Barbados around 06:00 UTC on September 30, as indicated by many ship and land observations.

The short-lived cyclone moved northwest and then north ahead of an approaching trough, acquiring peak winds of 45 mph (72 km/h) shortly after formation before presumably dissipating on October 3.

[2][10] On the second week of October, a broad area of low pressure began to take shape along a frontal boundary across the northeastern Atlantic.

[2][10] The hurricane intensified significantly during this period, quickly attaining Category 4 intensity before reaching its peak strength with winds of 145 mph (233 km/h) on October 18.

The storm made landfalls over Isla de la Juventud and the Cuban mainland at peak intensity later that day,[2] passing 10–15 mi (16–24 km) west of Havana.

[10] Its center passed over the Dry Tortugas as a major hurricane late on October 18, before striking Sarasota, Florida, the following morning with winds of 105 mph (169 km/h).

[10] The storm weakened slowly over the Florida Peninsula, and the system eventually transitioned into an extratropical cyclone over South Carolina on October 20.

[9][10] The hurricane proved to be an important test of the American radiosonde network, whose upper-atmosphere data were successfully incorporated into tropical cyclone track forecasting, the first such instance on record.

[15][16] At least 300 people were killed in Cuba, though the full extent of casualties remains unknown as reports from rural areas of the island were never compiled.

[9] Heavy rains and gusty winds were felt throughout the Eastern Seaboard from the hurricane and its extratropical remnants,[11][20] causing widespread power outages.

The next cyclone, and the final system of the 1944 Atlantic hurricane season, developed from a frontal low east-northeast of Bermuda on November 13.