The 1777 Loyalist Jailbreak in Orange County, New York

John McAlpine: A Loyalist Caught in Revolutionary Upheaval

John McAlpine, a Scottish immigrant in upstate New York, remained loyal to the British Crown during the Revolution. Driven from his farm by Patriot forces, he fled to Canada and aided British operations, including supplying General Burgoyne’s 1777 invasion. Captured near Fort Ticonderoga, he was later released in a prisoner exchange but continued recruiting for the British cause. By late 1776, McAlpine was jailed in Poughkeepsie for treasonable correspondence and enlistment.

"Jailbreak! Tories Storm the Gaol" – The January 1777 Rescue

In January 1777, nineteen Loyalists—many McAlpine’s kin—stormed the Poughkeepsie jail and freed him. Traveling by night for 26 days, they reached British lines and joined Colonel Fanning’s King’s American Regiment. The Newport Gazette praised McAlpine as “a brave and hearty friend to his King,” and the jailbreak became a celebrated Loyalist exploit.

Patriot Response and Captain James Stewart’s Pursuit

Alarmed, Patriot officials dispatched Captain James Stewart to pursue the escapees. His expedition cost nearly £59, reimbursed by the Commissioners for Conspiracies. Though most Loyalists evaded capture, the Committee gathered evidence of McAlpine’s recruiting efforts, including testimony from Peter Drummond. The incident revealed the depth of Loyalist organization and the challenges of maintaining Patriot control.

Orange County’s Political Climate and Revolutionary Impact

Orange County was deeply divided. Governor Clinton noted jails were full of Tories, yet Loyalist raids persisted. Claudius Smith, another Loyalist outlaw, also escaped jail in 1777. These events led to increased militia presence, stricter security, and harsher punishments. Smith was eventually captured and executed in 1779.

McAlpine’s escape boosted Loyalist morale. He continued serving Britain and later resettled in Nova Scotia, publishing a memoir in 1780 recounting his adventures. The jailbreak exemplified the Revolution’s civil strife, where neighbors clashed over allegiance. It forced Patriots to confront internal threats and shaped the postwar social order in New York.

Sources

• Contemporary accounts in the Newport Gazette and Loyalist Institute
• Minutes of New York’s Commissioners for Conspiracies
• Public papers of Governor George Clinton
• The History of Orange County, NY
• Dictionary of Canadian Biography