Thomas Cummings, a Scot, was John Burch's farm manager at Pappacunk, in the Catskills in New York. In the Revolutionary War, Cummings fought as a Loyalist and so in 1783 was granted 200 acres across the Chippawa Creek from his old boss. There he built his home in a pine grove and settled there with his mother, who had been Burch's housekeeper. He married Jane Christie in 1788 and the next year became the father of James, the first white child born in Chippawa. Two years later, his daughter Jane was born. She became the wife of James Crooks.

Thomas worked for the Commissiarat Department until 1815. When the British gave up control of Fort Niagara, Chippawa was chosen as the site for new warehouses and a fort. Fort Chippawa and a storehouse were built on property appropriated from Burch. Cummings built warehouses across the creek and operated as a general merchant.

During the War of 1812, the Lincoln Militia under Col. Thomas Clark were posted to Chippawa and used Cummings' warehouses as a barracks. In December 1813, these warehouses were destroyed by the militia. In the following July, the forces of Generals Riall and Scott fought the Battle of Chippawa and the village was devastated. Cummings alone claimed nearly £2500 for buildings and property damaged.

Thomas Cummings died in 1823 and is buried in the cemetery of Holy Trinity Church..

In 1807, James Cummings began to run his father's business but by 1811 he had started up in business for himself. He too was a general merchant buying goods from the US rather than Montreal.

In the War of 1812, James fought with the 3rd Lincoln Militia, being promoted to Captain in 1813. He took part in many raids with Hamilton Merritt's Daredevils and Fitzgibbon's Bloody Boys.

After the war, James resumed his business. By the 1830s, the merchants along the Niagara River were beginning to suffer as the Welland Canal began to lure traffic from their businesses. In 1831, James, along with Thomas Clark, Samuel Street Jr., and others applied for a charter to build a railway. After much opposition from the backers of the Welland Canal had caused considerable delay, the charter was granted in 1835 and the Erie and Ontario Rail Road Company came into being. The relatively smooth section from Niagara Falls to Chippawa began to operate in 1839. The section from Queenston to Niagara Falls took longer because it had to get up the slope to the Queenston Heights. The railway was horse-powered: three horses being required to pull the train up Queenston heights but only one being required for the rest of the trip.

James was a Member of the Legislative Assembly for many years, and, when Chippawa was incorporated as a village in 1849, James was the first reeve. The square at the foot of the bridge across the Welland River is called Cummington Square after James. Between 1830 and 1840, he built a grand house, Willoughby Hall, on the banks of the river between the bridge and the Niagara River. The house is still there, though now it is called Willoughby Manor and is a retirement home.

James Cummings and family outside Willoughby Hall

Willoughby Manor near the same spot