The Tallahassee, an English built steamer, was originally employed as a trade steamer for the East Indian Trade route. Later, after being fitted with guns, she was converted to a gun boat.

In August 1864, during the American Civil War , the Confederate blockade runner,Tallahassee, came into Halifax Harbour. Badly damaged, she was in need of repairs and to restock coal. Captained by J. Taylor Wood, the Tallahassee was allowed a limited time in a neutral port under British law. The following day, despite much protest from the Northern States, the Tallahassee received an extension of 24 hours because mast repairs were not complete.

Reportedly , two Union cruisers were sitting off Chebucto Head waiting for the Tallahassee to leave Halifax Harbour. Captain Wood had to plan an escape. The only chance of getting out of the Harbour without having to contend with the Union cruisers, was a daring and dangerous route through the narrow Eastern Passage. The Eastern Passage is a channel between McNab's or Lawlor's Island and the mainland of Eastern Passage. (Anyone who has walked on the boardwalk at Fisherman's Cove , has seen this channel.)
A ship as large as the Tallahassee had never before passed through this shallow channel.

Jock Flemming, a senior Harbour pilot from Ketch Harbour came highly recommended to Captain Wood, and so he chose Flemming to guide his ship out through the Eastern Passage.

At high tide on August 20, under the cover of darkness , the Tallahassee left it's wharf and headed out of Halifax Harbour toward the Eastern Passage. She started her dangerous escape. With all lights extinguished, they would have to feel their way out. A boat was sent ahead to check for depth and mark the turns.

By midnight, the crew could see the lights of Devil's Island. Once the Tallahassee was off Devil's Island , Flemming lowered his boat into the dark water, successful after confidently demonstrating his mastery of the Harbour waters. Once the Tallahassee reached deep water it was full steam as she headed back to North Carolina, undetected by the enemy cruisers, Nasemount and Huron. The two cruisers after learning of the escape headed for the gulf of St. Lawrence as that is where Capt. Wood had hinted he was going. The Tallahassee arrived safely in Wilmington, late summer, 1864.

One of the Elementary schools in Eastern Passage, Tallahassee Comunity School, is named after the famous vessel.