[1][2] Despite objections from his father, he desired a better education than the rudimentary courses he received in the local school, so he studied surveying and then began a career as a schoolmaster.

Moving to Dexter, Maine, at the age of 21, he was forced to confront unruly pupils who had "flogged and ejected" the last several teachers who had attempted to discipline them.

"[2] Although he received some military experience fighting Indians as a colonel in the Maine militia in the 1830s,[3]: 196  the majority of his time before the Civil War was engaged in a variety of business pursuits.

[4] He was prominent in civic affairs as a selectman, director of a railroad, trustee of Tufts College, and a member of the Maine State Senate in 1841.

"[7]: 19  During the fighting against Stonewall Jackson at Brawner's Farm, Cutler was severely wounded in the right thigh, causing him to miss the Maryland Campaign and the Battle of Antietam of September 1862.

[3]: 196 In the spring of 1863, Cutler was given command of the 2nd Brigade, James S. Wadsworth's 1st Division, I Corps, which he led at the Battle of Chancellorsville in May, but his unit was only lightly engaged.

For the remainder of the three-day battle, Cutler's brigade occupied defensive positions on Culp's Hill and, taking advantage of the entrenchments there, suffered few additional casualties.

At the Battle of Globe Tavern on August 21, 1864, he was struck in the face and badly disfigured by a shell fragment and he was forced to leave field command.

He died from a stroke,[7]: 20  which doctors attributed to complications from his Globe Tavern wounds,[3]: 197 [note 1] in Milwaukee, Wisconsin, and is buried there in Forest Home Cemetery.