During the Battle of Long Island, which led to British victory and the capture of New York City, via a flanking move from Staten Island across Long Island, Hale volunteered on September 8，1776，to go behind enemy lines and report on British troop movements. He was ferried across on September 12. It was an act of spying that was immediately punishable by death, and posed a great risk to Hale.
在长岛战争期间，英国通过侧面攻击从斯塔顿岛到长岛的移动的方式取得了胜利，并占领了纽约城。1776年9月8日，在长岛战争中，黑尔主动到敌方后线去侦查英军的动向。他于9月12日被横渡过去，在这次间谍行动他受到惩罚，黑尔的生命受到威胁。
During his mission, New York City (then the area at the southern tip of Manhattan around Wall Street) fell to British forces on September 15, and Washington was forced to retreat to the island's northern tip in Harlem Heights (what is now Morningside Heights.)-On September 21, a quarter of the lower portion of Manhattan burned in the Great New York Fire of 1776. The fire was later widely thought to have been started by American saboteurs. to keep the city from falling into British hands, though Washington and Congress had already denied this idea. It has also been speculated that the fire was the work of British soldiers acting without orders, intending to punish and/or intimidate any remaining Patriots in the city - with unintended consequences, however. In the fire's aftermath, more than 200 American partisans were rounded up by the British.
9月15日，他执行任务期间，纽约市（当时在纽约曼哈顿华尔街周围南端区）落到英军的手里。华盛顿被迫撤退到海岛的哈莱姆区高地（北端在现在莫宁赛德髙地)。 9月21日，曼哈顿楼低层的四分之一在纽约市的大火中被烧毁。后来人们普遍认为大火是由美国破坏者发起，以防止纽约落入英国人手中，尽管华盛顿和国会已经否认了这一说法。也有人推测， 火灾是无命令行事的英国士兵的发起，打算惩罚和或恐吓任 何留在城市爱国者，但却带来了意想不到的后果。在火灾结束后，200多名美国游击队员被英军围捕。

An account of Nathan Hale's capture was written by Consider Tiffany, a Connecticut shopkeeper and Loyalist, and obtained by the Library of Congress. In Tiffany's account, Major Robert Rogers of the Queen's Rangers saw Hale in a tavern and recognized him despite his disguise. After luring Hale into betraying himself by pretending to be a patriot himself, Rogers and his Rangers apprehended Hale near Flushing Bay, in Queens, New York. Another story was that his Loyalist cousin, Samuel Hale, was the one who revealed his true identity.
美国国会图书馆从一个名叫考律蒂芙尼的康涅狄格保皇派店主获得了内森黑尔被捕时的情况描述。蒂芙尼的描述中称，尽管黑尔伪装了自己，女王的流浪者队陆军少校罗伯特罗杰斯在一个小酒馆里看到黑尔并认出了他。他假装自己是一个爱国者引诱出卖了黑尔，罗杰斯和他的流浪者队在在纽约皇后区的法拉盛湾附近拘捕黑尔。另一个故事说，黑尔的保皇派表弟，塞缪尔黑尔，才是表露他真实身份的人。
Statue of Hale, sculpted 1908-1912 by Bela Lyon Pratt, was cast in 1912 and stands in front of Connecticut Hall where he resided while at Yale. Copies of this sculpture stand at the Phillips Academy in Andover, Massachusetts; the Nathan Hale Homestead in Coventry; the Connecticut Governor's Mansion in Hartford, Fort Nathan Hale in New Haven, the Department of Justice in Washington, D.C.; Tribune Tower in Chicago; and at the headquarters of the Central Intelligence Agency, Langley, Virginia.
黑尔的铜像，于1908年由贝拉里昂普拉特开始雕刻，铸成于1912年，被安放在他在耶鲁居住过一段时间的康涅狄格州厅前。这个雕像的复制品被安放在马萨诸塞州安多弗菲利普斯学院，内森黑尔在考文垂的宅基地。康涅狄格总督在哈特福德的大厦堡，在纽黑文，华盛顿特区的司法部，在芝加哥的论坛大楼。以及在兰利的中央情报局，在弗吉尼亚州的总部等很多地方。