The Pioneers was the first of the Leatherstocking Tales to be published (1823). It takes place in and around an upstate New York town with thinly veiled parralels to Cooper's home of Cooperstown, with the character of Judge Marmaduke Temple an equally transparent analog to the author's father Judge William Cooper.

The story starts on Christmas Eve, 1793, with Judge Temple bringing his daughter Elizabeth (Bess) home to Templeton by sleigh after a number of years of formal schooling in New York City. The sleigh is driven by Aggy, a black slave, and all are bundled in furs against the cold. Bess is to become the lady of Temple's manor house after the recent death of his wife.

A few miles from Templeton, within Temple's patent, they hear a dog barking, which Temple recognizes as Natty Bumppo's old hound Hector. The juge then spots a deer and pulls out his fowling piece. He fires, but the deer bounds away, then falls after a louder shot is heard. The aging Natty (Leather-Stocking) and a young stranger come out of hiding, and a discussion ensues about who shot the buck and who will take it home. Natty remarks that the Judge's fowling piece is insufficient for deer hunting, and the stranger points out that all but one of Temple's pellets are in a nearby tree. The Judge still claims that the one piece of shot could have brought the deer down, but the stranger proves him wrong by showing the hole in his shoulder caused by the projectile.

The Judge convinces the young man to accompany them with the deer to Templeton to have his wound attended by the town Doctor. As they depart, Leather-Stocking shoots a pheasant and they leave him to spend Christmas Eve in his own cabin with his freshly killed dinner.