The CSS Tallahassee was a twin-screw steamer and cruiser in the Confederate States Navy, purchased in 1864, and used for commerce raiding off the Atlantic coast.

Tallahassee was granted an extra 12 hours to fix a broken mast but was only allowed to load enough coal to take her to the nearest Confederate port.

Wood hired legendary Halifax pilot John "Jock" Flemming, who guided the warship through the narrow and shallow Eastern Passage between Dartmouth and Lawlor Island, a route only suited for small fishing vessels.

The first Northern warship, the gunboat USS Pontoosuc, arrived at the harbour entrance several hours after the Confederate cruiser departed.

The battery had been removed and she ran through the Union blockade on 24 December 1864 while the United States fleet was preoccupied with bombarding Fort Fisher.

Wilkinson made two attempts to enter one of the southern ports, but finding it impossible, he took Chameleon to Liverpool, England, and turned her over to Comdr.

On her arrival in England on 9 April 1865 the Chameleon was seized and sold by the British authorities and was about to enter the merchant service when the United States instituted suit for possession.

[3] In 1958, a new school in Eastern Passage, Nova Scotia, near Lawlor Island, was named after the Tallahassee to commemorate Flemming's 1864 navigational feat.