Lee’s orders called for his cobbled-together division to move toward the enemy encamped around Monmouth Courthouse at 3 a.m. A six-hundred-man detachment under Colonel William Grayson was to lead the procession (and double as the observation force Washington had requested); because of confusion over finding local guides, however, its first elements did not actually depart Englishtown until almost 6 a.m. In the interim, Lee was receiving reports from General Dickinson. At 5 a.m. Lee learned that the British had begun moving out some thirty minutes earlier. Then, around 8 a.m., even as the tail of his strike force was clearing Englishtown, Lee heard from Dickinson that the British were still around Monmouth Courthouse in strength. Both reports were correct, though Lee thought them conflicting since the first referred to the departure of Clinton’s leading division and the second to his trailing one.

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Dickinson’s first report was sent in duplicate to Washington, then traveling with the main body some three miles west of Englishtown. Once the army was marching, Washington dispatched an aide to Lee to let him know that support would be close at hand. What seems clear at this point is that Washington wanted there to be an attack on the British, though his instructions did allow Lee to refrain if ‘there should be very powerful reasons to the contrary.’ Statements such as these served only to reinforce Lee’s understanding that, as the commander of the advance force, he was sanctioned with what he later termed ‘a very great degree of discretionary power.’

Washington’s aide found Lee puzzling over Dickinson’s follow-up report. According to that aide, Lee ‘exclaimed against the contradictory intelligence’ he had received. Several of Lee’s unit commanders sought him out to discuss the matter and, not surprisingly, there was no clear sense of the enemy’s design. About three miles east of Englishtown, Lee reached the Tennent Meetinghouse, where the road jogged southward along a ridge before continuing eastward.

Descending from the high ground, Lee crossed the lone bridge spanning the swampy passage of Spottswood Middle Brook, also referred to as the West Morass. He met the militia commander, General Dickinson, and William Grayson on the other side. The militia leader, whose men had already had a sharp scrap with a small British detachment that morning, issued a warning. ‘General Lee,’ he declared, ‘…if you march your party beyond the ravine now in your rear, which has only one passage over it, you are in a perilous situation.’ Lee declined the advice, though he did take the precaution of grouping his three leading regiments (perhaps one thousand men) plus Lt. Col. Eleazar Oswald’s four cannons under the command of Anthony Wayne, and at the same time placed Lafayette in charge of what had been Wayne’s detachment. Lee also decided ‘to march on and ascertain with my own eyes the number, order and disposition of the enemy, and conduct myself accordingly.’

The American procession continued eastward, passing the Parsonage farm and next the Rhea farm, then tenanted by a merchant named William Wikoff Jr. It marched in fits and starts as each new piece of information was evaluated. Lee scouted ahead toward the courthouse and observed British cavalry and infantry shielding the Middletown Road at a point just north of the village. The tardy nature of the Continental advance that morning had an unexpected benefit. When the early morning hours passed without the appearance of any significant American force save the pesky militia, Sir Henry Clinton’s anxiety about his wagons (now some four hours away) convinced him to depart with most of his trailing division, leaving only a small detachment (possibly thirteen hundred cavalry and infantry altogether). It was this rear screening force that Lee targeted.

Lee rejoined his column and instructed Wayne to push ahead with his three regiments to engage the enemy, apparently intending that the Pennsylvanian follow the route into the village. But as Wayne’s units approached Monmouth Courthouse, he learned from a local guide of a little-used road that would take him around the right flank of the British line. Without advising Lee, Wayne proceeded to carry out his flanking maneuver.

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