Leutenant Colonel Francis Smith of the 10th Regiment of Foot had seldom felt less dignified than he did on that April day in 1775. He was wearing an old-fashioned broad-brimmed hat and an old gray coat. Beneath his leather breeches were cheap blue stockings. His belongings were tied up in a handkerchief with a stick thrust through it and slung over his shoulder. And the man he was traveling with, John Howe, was not even an officer! But orders were orders, and General Thomas Gage had detailed the two men to pose as journeymen looking for work and to locate the supplies Gage knew the Whigs were collecting.

Smith was chosen for the mission because he would lead the column that would seize those supplies and forestall open rebellion in Massachusetts. Howe, a 22-year-old sergeant of the 52nd Foot, accompanied him because Howe had already made two previous spying expeditions. A few weeks earlier, Gage had sent Captain William Brown of the 52nd Foot and Ensign Henry De Berniere of the 10th Foot to map the roads to Worcester, where he suspected the American seditionists had cached a quantity of ammunition and weapons, including cannons. Brown had insisted on taking his batman, John Howe, and Howe proved to be an invaluable member of the team on that expedition and on a later one to Concord.

Smith and Howe set out before dawn. They had taken a rowboat to Cambridge, then walked west. Smith, called ‘Fat Francis by his troops (when he wasn’t around), was an old infantryman and did not mind walking. After traveling six miles on an empty stomach, though, he told Howe they were going to stop at a tavern for breakfast. The tavern belonged to Jonathan Brewer, an ardent Whig who would later command troops at the Battle of Bunker Hill. His employees shared his views.

A black waitress–whether she was a slave or a freedwoman is unknown–approached the Britishers. Smith, before ordering, asked her if she knew where they could find work.

Smith, the young woman replied, you will find employment enough for you and all of General Gage’s men in a few months.

That reply, Howe later reported, about wound up our breakfast.

A hasty retreat from the inn would have confirmed any suspicions, so Smith tried to brazen it out. When the tavern owner came around to ask how they liked their breakfast, the colonel said, Very well, but you have got a saucy wench here. Brewer agreed she was a saucy wench; he also said that she had been living in Boston and had got acquainted with a great number of British officers and soldiers and might take you to be some of them. He told them they could probably find work up the road.

The two Englishmen paid their bill and got out of sight as quickly as they could. Hiding behind a stone wall, they agreed that it would be dangerous for Smith to continue. The colonel gave Howe his journal book, 10 guineas and letters from Gage addressed to various Tories. He promised the sergeant a commission if he got back alive. Then Fat Francis took off, as Howe later described it, running through the barberry bushes to keep out of sight of the road.

Howe continued on to Waltham, telling people he met that he was a gunsmith, expert at making and repairing all types of arms, but that he had not yet raised enough money for a shop of his own.

A farmer told him to go to Springfield, where they were in want of hands to work at that business. Springfield was about 100 miles away, suggesting to Howe that the provincial congress was expecting British thrusts deep into the heartland.

The farmer asked Howe if he would like a drink. The sergeant said he would greatly appreciate a New England and molasses. The drink, rum sweetened with molasses, was popular in New England, but (understandably) unpalatable to anyone from anywhere else. During that period of heavy immigration from England, accent was a poor indicator of nationality. A request for a New England and molasses, though, would be considered a sure sign that the asker was a local person.

Walking on, Howe met a trapper in Weston who, in the course of conversation, casually pointed out a large tree near a causeway and said the townspeople were going to cut it down to stop the regulars from crossing with their cannon. Howe wondered where he could find a drink, and the trapper directed him to two taverns. He recommended the first, kept by Joel Smith, a good tavern and a good liberty man; the other was kept by Captain Isaac Jones, a wicked Tory, where a great many British officers go from Boston.

Howe arrived at Smith’s tavern at the same time that two teamsters from Boston came out to harness their teams. They had heard about the two suspicious journeymen in Watertown, and they gave Howe a hard look as he approached.

He looks like one of them rascals we seen in Boston, one of them said. Howe ignored them, went inside and ordered another New England and molasses. But one of the teamsters followed him in and told the landlord his new customer might be a spy. Howe remarked that he had actually come from the other direction–from Springfield, where he had been gunsmithing. He said he had grown tired of Springfield and trekked east, but his money was running low and he needed work. The landlord said that he didn’t have any jobs himself, but suggested that the other tavern owner, Captain Jones, might give him temporary work.

That gave Howe a chance to deliver Gage’s letter, but it was also a Patriot trap. If Howe lingered at the Tory’s tavern, the Patriots would be sure that he was a spy. Jones had his hired man take the Englishman out the back door to the home of a Loyalist named Wheaton. Soon after, a party of Whigs called at Jones’ tavern and unsuccessfully searched for the suspected spy.

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