Orange County
Historical Society

Corridor Through the Mountains

Smith's Clove: Wartime Line of Communication and Passageway for the Continental Army, 1776-1783

Richard J. Koke

[Editor's Note: Richard J. Koke authored a series of five articles that appeared in Volumes 19 -23 of the OCHS Journal between 1990 and 1994. These articles will be presented in multiple sections over the next few years.]

Part II:
War in the Clove
Chapter 1:
Prelude to War

Seventeen seventy-five was the year of the siege of Boston and of the Canadian invasion; a year in New York when royal authority was usurped by extra-legal congresses and committees. In Orange, it was a year of preparation and watchful waiting while the fighting went on elsewhere.

"The Retreat through the Jerseys, November 1776" Illustrated by Howard Pyle. Courtesy New-York Historical Society.

With the reorganization of the county militia in conformity with a new militia law adopted in August by the Provincial congress, Cornwall precinct was divided into seven districts or drumbeats, each required to furnish one company for the precinct regiment - at that time, the East Orange north of the mountain - then under recruitment by Colonel Jesse Woodhull, the enterprising Blagg's Clove farmer, sheriff and delegate to congress.

Three of the districts were fixed in Smith's Clove and the company commanders of each were chosen by the associators in their respective drumbeats who had subscribed to the General Association supportive of the Continental Congress. In conformity with the elections and commissions dated and issued on September 14, 1775, Francis Smith, tavern keeper, was commissioned captain of the Woodbury Clove Company, formerly under command of his elder brother Austin; Garret Miller was commissioned captain of the Upper Clove Company; and Steven Slot, tavern keeper, was commissioned captain of the Southwest Company, so-called because his drumbeat lay "in the Southwesterly parts of the precinct" abutting onto the Sidman lands and Precinct of Haverstraw. When Woodhulls regiment - later the 1st Orange - was ordered into Fort Montgomery in the summer of 1777, the Clove companies of Captains Miller and Smith were among the several that were sent across the mountains to the Popolopen fort.

The mustering of precinct companies, interestingly, was coincidental with an early wartime journey through the Clove by a commission charged by the Continental Congress in Philadelphia to treat with the Six Nations. Contrary winds on their return down the Hudson from Albany in September forced them to debark at Newburgh to finish the trip by land through the mountains.

A fourteen-mile journey brought them and their cavalry escort to Francis Smith's tavern in the Clove where they spent the night, and on the next morning they continued with intent to cross into New Jersey and reach Hackensack by nightfall. Tench Tilghman, their secretary and treasurer, remembered the trip well and had nothing good to say about it. "Tho' we were prepared for [a] bad Road," he wrote, "we found it worse than we expected, the whole way till within 14 miles of Hackensack thro' the Gap of the Mountains. It put me in mind of Don Quixote's rambles."

From what he related, it is quite apparent their dreary journey was even more arduous than that taken by Jeffrey Amherst on the same road fourteen years earlier, and that the Clove Road, soon to be a lifeline of the Continental Army, had advanced but little from its early primitive state.

Twelve days after his hosting of the Indian commission of the thirteen rebellious colonies at his mountain tavern, innkeeper Smith was accorded his captain's commission for the Woodbury Clove Company.

With the coming of 1776, the center of military operations transferred to New York, where Washington and the Contimental Army was dug in to defend the city and the Hudson River estuary against the British attack that was expected by sea. The campaign was a disaster for the Americans. The high hopes of early spring - the defense was essentially because of political considerations - vanished in the course of hard-fought battles and skirmishes, adroit naval exploits, and in withdrawal and retreat that finally brought both armies into Westchester in October, and after a drawn battle at White Plains they turned their backs on one another and moved in opposite directions - Washington to Peekskill, and Sir William Howe to the investiture of Fort Washington on northern Manhattan which still blocked the Hudson to the ships of the Royal Navy.

On November 11, one day after his arrival at Peekskill from central Westchester, Washington, accompanied by five generals and his chief engineer, reconnoitered the Highland defense at Forts Montgomery and Constitution on the river and on the following day examined the Gorge of the Mountains in northern Westchester; and on his return to Peekskill assigned command of the Highland posts on both sides of the Hudson to Major-General William Heath with orders that they be made secure with all possible haste and a proper distribution of troops be made.

All through 1775 and 1776, attention had focused on the defenses commanding the river, and it was only with the withdrawals from the lower Hudson and imminence of operations in New Jersey, coupled with the establishment of a new defense line across northern Westchester and along the Highland barrier, that attention was further directed to the passes and roads leading into and through the mountains.

The security of the river remained paramount throughout the war, but by the end of 1776 it was also obvious that the passes had to be blocked to prevent flanking movements through the mountains east and west of the Hudson that could allow the forts to be bypassed and permit land passage into the upriver country or attacks on the river positions from flank and rear. When security of the river was mentioned, it was always in conjunction with the security of the passes.

In his written instructions to Heath on the twelfth, before departing for New Jersey, Washington pointedly ordered him to secure the passes without delay, including that "on the west side of Hudson's River," and not lose one moment in selecting grounds where works should be erected, not only because of military necessity but, considering the late season of the year, before frost could impede spadework. He suggested that the cheapest kind of barracks be erected, preferably of logs.

The security of the western pass -- Tilghman's Gap of the Mountains -- had already been discussed by Major-Generals Nathaniel Greene and William Alexander, titular Earl of Stirling, who wrote to the commander-in-chief from Haverstraw on November 10: "The great pass through Highland lies fourteen miles back from the river, and will be best supported with troops from Tappan; and on consulting General Greene, a proper body of troops will be sent there."

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