Pilot Grove was an important landmark on the trail from Dubuque to Waterloo. It was a grove of oak trees situated on high ground that was visible for miles. Travelers from the east looked for Pilot Grove and used it as a guide for the last few miles into Waterloo. An inn was even located here at one time.

The field notes of the original survey of Barclay Township mention the grove as being about 50 acres in size, located in the west half of the northeast quarter of Section 30.

The trail that crossed the Wapsipinicon River at Independence ran westward north of Jesup and on to Pilot Grove, then southwesterly to the Elk Run Creek Crossing, where it met the trail from Davenport. The completion of the Dubuque and Sioux City Railroad to this point by 1861 made the trails less important and landmarks such as Pilot Grove unnecessary.