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"Middlebrook encampment" may refer to one of two different seasonal stays of the Continental Army in central New Jersey near the Middlebrook in Bridgewater Township in Somerset County. They are usually differentiated by either the date of the encampment or their chronological order (First vs Second). The First Middlebrook encampment refers to the spring encampment of the Continental Army, commanded by General George Washington, during the American War for Independence near the Middle Brook in Bridgewater Township, New Jersey (between Martinsville and Bound Brook) in 1777. The second, longer winter cantonment took place in 1778–1779, from December 1 to mid June. A cantonment is a protracted quartering of an army in a specific location, typically for the duration of the winter. A portion of the first encampment site, known as the Washington Camp Ground, was added to the National Register of Historic Places on July 3, 1975. The Campground is located in Martinsville, a section of Bridgewater Township. The Middlebrook Encampment site includes part of the ridge of the First Watchung Mountain. Its position provided a natural fortress not only protecting the Continental Army but also overlooking the plains towards New Brunswick, where the British forces were stationed in 1777. A surviving earthen redoubt believed to date to the 1777 encampment is also located on the mountain within Washington Valley Park. The strategic strength of the army's position on the Watchung or Blue Mountain ridge contributed ultimately to the success of the Continental Army by lengthening the war and wearying the British forces during both of the army's stays.

During the winter of 1776–1777, Washington initially encamped the Continental Army at Morristown, New Jersey. After his outpost garrison at Bound Brook was surprised and routed during the Battle of Bound Brook on April 13, 1777, Washington moved the encampment closer to Bound Brook. The army established its Middlebrook encampment on May 28 and stayed there until July 2. A total of 8,298 soldiers were housed in the encampment, but 2,660 of them were sick or disabled, unable to fight. In contrast, the British maintained a force of about 17,000 near New Brunswick, New Jersey. From the heights of the Watchung Mountains, Washington could monitor and counteract British movements. When General Howe decided to move against Philadelphia, concern over the threat by the Continental Army made him choose the safer sea route instead of the faster land route. This led to a significant delay in operations for the British and disrupted plans to reinforce British General Burgoyne in northern New York. On June 30, Howe moved his troops to Staten Island in preparation for his Philadelphia campaign, and two days later Washington left Middlebrook and moved the army to Pompton Plains, New York.

It is largely conceded that it was at the Middlebrook encampment that the first official flag of the United States was unfurled, after a law to adopt a national flag had been passed by Congress on June 14, 1777. This event is commemorated annually since 1889 on July 4 with a changing of the flag, a reading of the Declaration of Independence, and the delivery of an historical address at the Washington Camp Ground. Also, by special order of Congress, a Thirteen Star Flag is flown 24 hours a day at the Washington Camp Ground. ==Second Middlebrook or the Middlebrook Cantonment (1778–1779) The hutting constructed at Pluckemin for the artillery camp was more elaborate. Washington himself rented the Wallace House (now a New Jersey State Historic site) in Somerville for six months to serve as "Headquarters Middlebrook" and paid Wallace $1,000 for this inconvenience. General von Steuben lived at the Staats House in South Bound Brook. General Henry Knox lived at the Jacobus Vanderveer House near Pluckemin with the Continental Artillery encamped at the Pluckemin Artillery Cantonment Site. on the hills above Pluckemin. Nathanael Greene lived at the Van Veghten House in Finderne. General William Alexander, Lord Stirling, and on occasion, General Richard Henry Lee, occupied the Philip Van Horne House in Bridgewater. All five headquarters are publicly owned National Register sites. The main body of the much larger British army was based in New York that winter. Washington again used the security of the Watchung heights to monitor their troop movements and maintain a strong defensive position. Various other sites related to the Middlebrook encampment are accessible to the public. These include Washington Rock State Park, an observation site on top of the Watchung mountain ridge, in Green Brook, Washington Valley Park in Bridgewater (nearby, but separate from, the Washington Camp Ground). A sign commemorating the encampment also stands in a now developed area, at the corner of Chimney Rock and Gilbride Roads in Bridgewater. All five colonial homes that served as headquarters to the Generals during the cantonment were preserved at various times by local organizations beginning in 1898 with the Wallace House and all are now National Register Sites open to the public. See their respective websites for further information. A driving tour of the Middlebrook Cantonment area is available from the Heritage Trail Association and a "Five Generals Tour" is organized by Heritage Trail with the cooperating sites of the Middlebrook Cantonment.