[1] It was preceded in Keene by a number of much shorter ventures, including The New Hampshire Recorder, The Cheshire Advertiser, The Columbian Informer, and The Rising Sun.
[2] On March 23, 1799, first issue of the New Hampshire Sentinel, a weekly paper was published by the owner, John Prentiss.
[4][5][6] In 1880, the founders grandson, William H. Prentiss, became part owner and worked as city editor.
In 1893, they incorporated, and Bertram Ellis, William Prentiss, Thomas Rand and Samuel Woodward became stockholders.
[4] In October, 1954, James D. Ewing, his wife Ruth, and business partner, Walter Paine, purchased the Sentinel, from Coffin, and the Prentiss family.
In May 2024, the newspaper sent out a memo to staff announcing it will switch to postal delivery, resulting in 11 independent carriers losing their jobs.
[12] In January 2025, the paper launched the "The Keene Sentinel Local Journalism Fund" along with a community advisory board.
[13] The Sentinel covers the city of Keene, and 30 towns in Cheshire County (Alstead, Chesterfield, Dublin, Fitzwilliam, Gilsum, Harrisville, Hinsdale, Jaffrey, Marlborough, Marlow, Nelson, Richmond, Rindge, Roxbury, Stoddard, Sullivan, Surry, Swanzey, Troy, Walpole, Westmoreland, and Winchester), Hillsborough County (Antrim, Bennington, Francestown, Greenfield, Hancock, and Peterborough) and Sullivan County (Acworth, Charlestown, and Langdon).