On one occasion, Outerbridge was serving aboard the steamboat "Robert E. Lee". Departing from Wilmington at about 9 p.m. (at high tide, which is when the large ship could get over Wilmington's sandbar), the "Robert E. Lee" joined a small fleet of blockade runners which was soon attacked by two Man-of-War ships, flanking the fleet on either side. The Man-of-Wars immediately attacked with heavy cannons, destroying a winch (and severely wounding a number of foreign sailors). One of them approached the "Robert E. Lee" close enough for small arms fire, though there were no casualties.
While the captain - Wilkinson - studiously ignored the attack, Outerbridge, the mate and a number of crewmen had gone to the forecastle to watch for other craft. A round shot hit close to Outerbridge, causing him to fall unconscious while the other crewmen fled. The following day, Outerbridge was commended by the ship's officers for his bravery, and the crew picked small bullets from the woodwork (but not, strangely and thankfully, from each other).
At the time, the "Robert E. Lee" was en route to Halifax with a number of Confederate officers on board. The Confederates were bound for England to collect two Man-of-Wars for the Confederate government (the "Viper" and the "Vixen"). Interestingly, the British government seized the officers and sent them to Bermuda. The "Robert E. Lee" also set course for the island.
Not all of Outerbridge's adventures in the Civil War would be as pleasant, as he would be twice captured by the North. One one of these occasions, he was serving on the steamer "Sirene". Originally owned by the British government and used as the Dockyard duty boat, the ship was mothballed and sold to Mr. Fininsey, the popular Confederate Consul in Bermuda. Fininsey deployed the "Sirene" to Wilmington with a crew, to bring back another steamship, the "Cape of Good Hope", to act as a cotton freighter. At the time, the "Cape of Good Hope" was a passenger boat between Wilmington and Smithfield, a role that the "Sirene" would then fulfill. Captain Jeremiah Peniston was selected as the ship's Master, with Outerbridge's brother, Eldon, as first officer and Outerbridge himself as second officer. A Virginian man by the name of Mr. Tab was the ship's Purser.
A week out of Bermuda, the rather slow "Sirene" reached the American coastline off Bowford, North Carolina. She head southwards towards Cape Fear under sail, hoping that it would deceive the Blockade fleet. Only an hour later, the Man-of-War "Key Stone State" (which was later purchased by a Mr. Webb of New York, renamed the "San Francisco" and used as a mail ship to, ironically, Bermuda) intercepted the "Sirene" and towed it into Bowford, with the crew having a merry laugh at the blockade runners' pitiful craft.
The following day, the crew were transferred onto a receiving ship in Bowford's harbour, where they found a welcoming presence in the ship's captain. Having visited Bermuda several times in a Whaler, the ship's captain was kind towards his prisoners. However, they spent the next ten days treated like fighting cocks. Four days into this, the "Sirene" crew witnessed another blockade running steamer, the "Pavince", being chased on shore by the Man-of-War. The steamer was fast enough that the crew had the leeway to abandon the ship and row ashore on small craft, but they were immediately captured by Union soldiers. The "Pavince" was at that time on fire, and exploded. With the crew of the "Pavince" - also familiar with the Captain from his time in Bermuda - aboard, the blockade runners "had a good time as long as [they] were there".
After the ten days, the blockade runners disembarked into Camp Hamilton, which was under military authority. Treatment was severe. Four days into the stay, the Union wardens sent all imprisoned masons - including the both blockade runner captains and some fifteen thousand Confederate soldiers.
At "Point Look Out", the blockade runners were stripped, with their possessions to be returned at the end of their imprisonment. Described conservatively as "a real pest hole", "Point Look Out" was a mile square, surrounded by fifteen foot tall lumber walls. Around this wall, stationed every thirty feet on a platform four feet from the top, Union soldiers kept watch. Many of these were former slaves liberated by the North, who apparently exacted their revenge by shooting Southern soldiers. Each morning, Outerbridge woke up to fifteen to twenty corpses for former Confederates.
The prison was hard for Outerbridge. Like the other prisoners, he had to sleep in the open air, and ate a loaf of bread a day (with a quarter pound of fresh beef delivered thrice a week). The wagons that delivered the daily bread "carried out something else". Luckily for him, however, Eldon had managed to sneak a Gold sovereign under his tongue. Eldon and Thomas used this money to trade with settlers immediately outside the camp, through a small hole in the wall. Initially, the brothers tried to send letters to Lord Lyon, the British Ambassador to Washington, requesting aid. These letters would never be received, however.
Mr. Tab - the "Sirene"'s Purser - would prove invaluable at this point. With the help of the local Chaplain, he managed to get a letter through, and soon the brothers were free.
Unfortunately, the money and possessions that had been removed from the brothers was nowhere to be found. With a gift enough to get them to New York, the brothers secured a loan from a Mr. Middleton, the Bermuda Agent, to pay for their trip back home (a loan that was promptly repaid). They returned to Bermuda as crewmen aboard the barque "Lapflerene", where they were well-treated by the captain - William Peniston - and his wife for the eight-day journey.
Upon returning to Bermuda, the crew made for Castle Harbour, proceeding up the old Quarry as close to the Outerbridge's homes at Bailey's Bay as they could get.
Near the close of the war, the Outerbridge brothers entered the employ on one John Tory Bourne. Bourne named them captain (Eldon) and chief officer (Thomas) of his "Sarah Ann". The ill-fated brig would be blown ashore and wrecked in a hurricane on the main island of St. Thomas
Thomas Outerbridge would also sail the "Harvest Queen", the "McMillian" and the "T.H.A. Pitt", as was the long-time Master of Mr. J.S. Darrell's tug "Clover". It is believed that the last sailing ship her had charge of was the brigantine "Peeress", belonging to one Mr. H.C. Outerbridge. Thomas took the "Peeress" north for general cargo and a deckload of livestock. On his return, the ship's well-kept glass readings showed an approaching hurricane. Outerbridge went north and then west of Bermuda to avoid the damaging storm. They finally arrived in Hamilton without any damage - attributed to Outerbridge's skill as a mariner.
He would marry Alice Hollis, and have five sons by her. Unfortunately, two of them - Gordon and William - would predecease them. Surviving him were Ernest Seon Outerbridge; Thomas Reginald Outerbridge; and George Harrison Outerbridge.
His funeral at the Holy Trinity Church was described as "very largely attended" - many attending from a distance - with numerous, beautiful floral arrangements. In attendance were his faithful follower John Virgin, his nephews F.C. Outerbridge, Bernard Wilkinson, Wickwire Davis, Stephen Wilkinson, Malcolm Hollis and Sturgis Davis (who acted as the carriers), and was performed by the Rev. Canon Earp, Rector of Hamilton and Smith's, and the Rev. A. T. Tucker, Rector of St. George's.