The land in what would become Dundas County was granted in 1784 to United Empire Loyalists, most of whom had fought with the King's Royal Regiment of New York during the American Revolution.

[2] The loft of Hummel's homestead served as the local gathering place during the early years of the village, and political meetings were often held there.

In December 1827, the Merkley brothers, Jacob (1794-1827) and Michael (1797-1827), travelled to Waddington, New York along with Solomon Sterns to secure supplies for a raising bee, but on the return trip a snowstorm blew over the St. Lawrence River and their canoe upset, drowning all three men.

[4] Historical records suggest that although the post office and village were officially named Winchester, the community was known locally as Chesterville as early as the 1840s, and for a short time as Hummelville.

[10] Many of the original early settlers in the Chesterville district were Scottish and Irish immigrants as well as some Loyalist Germans from Williamsburg, Matilda, Stormont, and Grenville.

[11] Following the destruction of the Second World War in Europe, many Dutch families immigrated to Canada in the early 1950s-60s, settling in the Chesterville area.

[12] Many of these immigrants would go on to become successful and prominent members of the community, and Chesterville district continues to be home to a large Canadian-Dutch population.

In May, a by-law was prepared by the village council to mandate that only "fireproof" buildings (such as brick and stone) could be constructed in the business section of town.

[18] After losing their printing presses in the fire, the Chesterville Record staff worked from a temporary office in Thomas McMahon's blacksmith shop on Main Street south of the CPR line.

Shelters were established throughout North Dundas, and Chesterville hosted 100 beds, 75 at the Fawcet Pub, and 25 at the Legion Hall.

The military history of Dundas County and Chesterville dates back to the early settlement days, when Loyalist veterans of the American Revolution were granted plots of land in Upper Canada and raised a local militia.

His son, John Irvin Ker, left Chesterville and fought in the American Civil War with the 4th Minnesota Infantry Regiment.

A prominent local man, Major Robert Gray, served as a captain in the 1st Dundas Militia at Prescott in 1838 and later commanded the 4th Winchester Battalion.

[25] With the passage of the Militia Act of 1855, the counties of Leeds, Dundas, Stormont and Glengarry became part of Military District No.

Militia officer lists for the 4th (Winchester) Battalion from the 1850s and 1860s include some early Chesterville district settlers: - Major George Fitchel (merchant/tavern keeper) - Captain Robert H. Rose (merchant) - Captain Giles W. Bogart (reeve) - Captain Matthew Rae (cabinet maker) - Captain John Capel (harness maker) - Lieutenant John Halliday (general merchant) - Lieutenant John McCuaig (merchant/clerk of the division court) - Lieutenant Alexander Stallmire (farmer) - Lieutenant David Rae (farmer) - Lieutenant William Hiller (grocer) - Ensign Henry W. Moad (blacksmith) - Ensign Ezra Fetterly - Ensign James O'Brien - Ensign Peter Bogart (general merchant) - Quarter Master Martin Coyne (trader) Men from Chesterville and district served during the Fenian Raids period, including Isaac Wingard and Joseph Dillabough who served with the Williamsburg Rifles.

The reserve militia existed until the early 20th century, with all men in the township nominally enrolled and an annual muster occurring.

Wesley B. Lawson from Chesterville served on active duty in Toronto with the 2nd Queen’s Own Rifles during the North-West Rebellion, and local doctor Robert Reddick was Assistant Surgeon for the Northwest Field Force.

[28] During World War One, many men from Chesterville served with the 154th (Stormont-Dundas-Glengarry) Battalion, CEF and other regiments in France and Belgium.

Men and women from Chesterville and district have since served in United Nations and NATO Peacekeeping missions around the world, and during the War in Afghanistan (2001-2021) and the newest generation of Chestervillians continue the legacy of military service.

On 10 November 1957, the Chesterville Legion unveiled the cenotaph on the grounds of the Community Hall (1 Mill Street) to honour those lost during the World Wars.

In the spring and summer of 2015, the park was updated and a new pathway, flag pole, and benches were installed, along with extra floodlights and shrubbery.

A new black granite monument was erected beside the original cenotaph and features the names of all the local veterans who served in the World Wars, Korea, NATO and UN missions, and Afghanistan.

A kiosk stands beside the clock, built in honour of Leon Marcellus, a prominent Chesterville businessman, and hosts regular historical displays.