These manly, wise, and patriotic words—this willingness to sacrifice himself, if necessary, for the good of his country—silenced his brother officers. Accompanied by Knowlton, he appeared before Washington the same afternoon, and received instructions concerning his mission. His commander also furnished him with a general order to the owners of all American vessels in Long Island Sound to convey him to any point on Long Island which he might designate.
Hale left the camp on Harlem Heights the same evening, accompanied by Sergeant Stephen Hempstead, a trustworthy member of his company, whom he engaged to go with him as far as it would be prudent. He was also accompanied by his trusty servant, Ansel Wright. They found no safe place to cross the Sound until they arrived at Norwalk, fifty miles from New York, owing to the presence of small British cruisers in those waters. There Hale exchanged his regimentals for a citizen's dress of brown cloth and a broad-brimmed round hat, and directed Hempstead and Wright to tarry for him at Norwalk until his return, which he supposed would be on the 20th. He directed a boat to be sent for him on the morning of that day, and left with Hempstead his uniform and his military commission and other papers.
There are somewhat conflicting accounts concerning Hale's movements after he left Norwalk. All agree that he was conveyed across the Sound to Huntington Bay, where he landed; that he assumed the character of a schoolmaster and loyalist disgusted with the "rebel" cause, and that he professed to be in quest of an engagement as a school-teacher. It is known that he entered the British camps in personal disguise and with the pretext of loyalty and the character of a pedagogue; that he was received with great cordiality as a "good fellow"; that he visited all the British camps on Long Island, made observations openly, and drawings and memoranda of fortifications, etc., secretly; that he passed over from Brooklyn to New York city and gathered much information concerning affairs there, the British having invaded Manhattan Island and secured possession of the town since his departure;[3] and that he returned to Long Island and passed through the various camps to Huntington Bay for the purpose of going back to Norwalk.
Tradition tells us that Hale was conveyed from Norwalk to Huntington Bay on a sloop, and was landed from her yawl two hours before daybreak in the neighborhood of a place called "The Cedars." Near there a Widow Chichester, a stanch loyalist (called "Widow Chich"), kept a tavern, which was the resort of all the Tories in that region. Hale passed this dangerous place with safety before cock-crowing, and at a farm-house a mile distant he was kindly furnished with breakfast and a bed for repose after his night's toil. Then he made his way to the nearest British camp, and was received without suspicion of his real character. Concerning his movements after that, until his return from New York, tradition is silent.
Hale, on his return, had reached in safety the point on the Long Island shore where he first landed, and prepared to recross the sound at Norwalk the next morning. He wore shoes with loose inner soles. Between the soles he had concealed the accurate drawings he had made of fortifications, etc., and also his memoranda, written in Latin on thin paper. He had given directions for the boat, from which he had landed, to come for him on a designated morning, which would be the next after his return. Satisfied that he was safe from harm, for he was remote from a British post, and happy with the thought that his perilous mission was ended successfully and that he should render his country most important service, he awaited the coming morning with patience and serenity of mind.
Feeling secure in his simple dress and disguised manner, Hale entered the tavern of the Widow Chichester, at "The Cedars." A number of persons were in the room. A moment afterward, a man, whose face seemed familiar to him, suddenly departed and was not seen again.
Hale passed the night at the tavern, and at dawn went out to look for the expected boat. To his great joy he saw one moving toward the shore, with several men in it. Not doubting they were his friends, he hastened toward the beach, where, as the vessel touched the shore, he was astounded by the sight of a barge bearing British marines. He turned to flee, when a loud voice called, "Surrender or die!" Looking back he saw six men standing erect, with muskets leveled at him. He was seized, taken into the barge, and conveyed to the British guard-ship Halifax, Captain Quarne, which was anchored behind a point of wooded land of Lloyd's Neck.
It has been asserted that the man who so suddenly departed from the room of the tavern at "The Cedars" when Hale entered was a Tory cousin of his, a dissipated fellow, who recognized his kinsman in disguise and betrayed him into the hands of the enemy; but there is no warrant for such an accusation.
Hale's captors stripped and searched him, and found the evidences of his being a spy in the papers concealed between the soles of his shoes. These formed as positive testimony as to his true character as did the papers found in André's boot, which convicted the adjutant-general of the British army of being a spy.