His men later recalled Allen making three owl hoots, his signal for them to follow him. Allen and the Boys slipped silently past the outer works of the fort. The ghostly line of frontiersmen hugged the crumbling granite south wall of the main, star-shaped fortress until they reached a breach where, after years of peacetime neglect, the stones had parted.

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When they arrived on the Vermont shore early the day before, Allen and his militia had been confident that it would be possible to enter and seize the strongest British fortress in North America by surprise. Allen had dispatched two of his subordinates, Captains Noah Phelps and Ezra Hickok, to stroll inside the fort and pass themselves off as a pair of fur trappers coming down from the hills to have their long, unkempt beards and matted hair trimmed by the fort's barber. Once inside, they'd had time to note the laxity of the sentinels, the poor condition of the walls, and the fort's strengths and weak spots.

Because he had so often been among them, Allen was aware that all sorts of people on the New York–Vermont frontier—hunters, trappers and fur traders, merchants, farmers and Indians—wandered in and out of the fort. Phelps and Hickok had been able to learn that the fort's main gates were no longer locked at night. Somebody even said that the keys had long ago been lost. Even better, Allen's two spies had discovered that the British garrison was made up of just forty-six regulars with their wives and children and two officers.

Ticonderoga's Redcoats had not yet heard that fighting had broken out far to the east, outside Boston, that hundreds of British regulars had been killed or wounded, and that a state of rebellion existed. Military dispatches or mail of any type did not travel quickly from Boston west to Lake Champlain. News that fighting had broken out nearly a month earlier had to be sent by Royal Navy courier aboard a man-of-war, first from Boston north to Halifax, Nova Scotia, then forwarded around eastern Canada and up the St. Lawrence River to Quebec. There, it had to be transferred to a supply ship that sailed only periodically from Quebec to Montreal, where the British officer in charge had to read it and write his own orders, to be put aboard another vessel that carried it south along the Richelieu River to St. Jean, in southern Quebec province.

After receiving a written warning two months earlier from the British commander in chief, Sir Thomas Gage in Boston, Ticonderoga's commander, Captain William Delaplace, had asked Sir Guy Carleton, governor-general of Quebec, for reinforcements. The first of those left Canada on April 12. A second group of ten, under Lieutenant Jocelyn Getham, arrived on April 29, but those troops did not know about Lexington and Concord.

On May 10, the communiqué describing the bloody battle outside Boston was aboard a sloop-of-war tied up at a dock in Canada, at Lake Champlain's northern tip, nearly 125 miles away from Fort Ticonderoga. However, that ship would sail for Ticonderoga any day now. With it would undoubtedly come British reinforcements and skillful resistance.

Allen knew the strategic importance of the mission. His targets were two of colonial America's most strategic strongholds, midway in a line of fortified lakes and rivers that ran from Quebec through Montreal to New York City. The keys to this chain of forts were Ticonderoga and, twelve miles to the north, Fort Amherst at Crown Point. To the south was another pair of forts at either end of Lake George, just to the north of the Hudson River, which was navigable all the way to the Atlantic Ocean. Unless they took Ticonderoga and Crown Point and controlled the 116-mile-long Lake Champlain, American revolutionaries to the south and east would be exposed to invasion from British bases in southern Canada. If the British kept control of Lake Champlain, they and their Indian allies could harass the Vermont and New York settlements, eventually splitting off rebellious New England from the more moderate Middle States.

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