Riding Southwest towards Millersburg, the gang came across a farmer driving his wagon. He noticed that Cole and Jim were riding on either side of Bob holding him in his saddle. He asked if he was their prisoner and one of the outlaws assured him that he was their prisoner and they were taking him to jail. The confused farmer told them they were going the wrong way. One of the outlaws turned and said, "Oh, no! We're taking the right way."

Eleven miles outside of Millersburg, the gang stopped a farmer and stole his horse because Bob's horse was weak. Later, they stopped another farmer and stole his saddle, but the girth broke spilling Bob Younger onto the road. Bob was once again put behind Cole.

Receiving a telegraph message, fifteen men from Faribault took off to Shieldsville. To the outlaws luck, the posse went into Haggerty's Saloon and left their guns outside. The gang rode into town and stopped in front of the saloon at a pump to take water for their horses and their wounds. One posse member tried to come out of the saloon but the gang pushed him back inside and rode off shooting.

The gang continued to ride on Old Dodd Road. The Faribault posse came close behind and started firing at the gang as they ascended a hill. Charlie Pitts was thrown from his horse. When he tried to re-mount, the cinch broke. He jumped up behind Bob Younger, whose horse was being led by Cole, and the gang went and hid in the woods. It was at this time a downpour of rain came into the area and it would last off and on for two weeks.

Famous from the Civil War, General Pope was put into charge of the round up of the gang. He established picket lines throughout Southern Minnesota and stationed everyone from law officers to volunteers to help capture the gang.

Near German Lake, the gang knew they were surrounded and abandoned their horses and took only their bridles. They managed to escape on foot though the picket lines. The Faribault posse didn't find the horses until the Twelfth. They could not find a reason as to why the gang escaped.

The outlaws, now weak and weary, have traveled less than fifty miles in five days; however, they did manage to slip through several picket lines. A couple of miles from Mankato, the gang came across a deserted farmhouse and stayed there for two nights. They needed to be cautious because now the reward for the robbers was now three thousand dollars a man and people saw that money in their pockets.

Minnesota was going through what some claimed was "the wettest two weeks." Due to this, many rivers were flooded and bridges deemed "unsafe." In Mankato, the gang kidnapped a local farm boy and commanded him to show them the way through the city and across the Minnesota River. Since the bridge was out, the gang had to cross at a shallow part in the river. After a mile, the gang turned the kid loose and he quickly told the sheriff.

A posse from Mankato and another from Lake Crystal searched the area around Mankato for the band of outlaws. At Minneopa Falls at six in the morning, the posse smelled smoke in the dense woods. As they went to investigate, they heard the scurrying of men on the other side of the ravine, but the woods was so dense they could not see them. The gang left behind a part of a roasted chicken, some green corn, a hat, and a rubber overcoat.

Just South of Mankato at Bush Lake (now called Rush Lake) the robbers escaped the woods from Minneopa Falls. They made the important decision to split up and go in different directions. The gang would split up into two, one group consisting of the James brothers and the other the Younger brothers and Charlie Pitts. Not only would the James brothers had a better chance of escaping, but they were more wanted making most of the posse's trying to capture them instead of the Youngers and Pitts; giving them a better chance of escaping also.

While the Youngers and Pitts traveled Southwest on foot, the James brothers headed West. It is unknown exactly where they went, but it is believed they went through the Southeast corner of South Dakota and headed South back home in Missouri.