[4] In 1797, he purchased a tract of land in Castalian Springs known as Bledsoe's Station and oversaw the construction of Cragfont, a Georgian style mansion that was completed in 1802.

In March 1812, three months before the war with Britain began, Winchester was commissioned a brigadier general in the United States Army.

Winchester's seniority was confirmed in September, but he was forced to relinquish command several days later when Harrison was commissioned a major general in the regular army.

[3] In October 1812, Winchester met with Harrison in Sandusky where he was ordered to move up the Maumee river and to take back Detroit from the British.

While on the march, he established Fort Winchester in north west Ohio, which was the forward observation post on the front lines against the British.

On January 18, he led his men across the frozen Raisin river and took Frenchtown from a small Canadian militia force, planning to use the town as a launching pad for an attack on Detroit.

However, his men were attacked four days later by Col. Henry Proctor leading a larger force of British regulars and Canadian militia, allied with Wyandot led by Roundhead who were able to retake the town in The Battle of Frenchtown.

Despite Procter's pledge, the Wyandot accompanying the British executed 68 seriously wounded American prisoners of war in the Massacre of the River Raisin.