Harris-Moore is suspected of being responsible for approximately 100 thefts in Washington, Idaho, and Canada, including bicycles, automobiles, light aircraft, and speedboats. It is believed that he learned how to fly small planes by reading aircraft manuals, handbooks, watching a "How to fly a small airplane" DVD, and playing flight simulator computer games
. One plane he stole was a Cessna 182 belonging to KZOK-FM radio personality Bob Rivers, valued at US$150,000. The plane was later recovered from the Yakama Indian Reservation, though it was so badly damaged that it was a total loss. According to local sheriffs, he would often slip into a home just to soak in a hot bath or steal ice cream from the freezer. Initially, he would steal only what he needed for living in the woods as a survivalist. Once, he allegedly used a homeowner's computer and credit card to order bear mace and a pair of US$6,500 night vision goggles.
On May 30 or 31, 2010, police found a handwritten note and US$100 at a veterinary clinic in Raymond, Washington, approximately 95 miles (150 km) southwest of Seattle. The note read:
Drove by, had some extra cash. Please use this money for the care of animals
—Colton Harris-Moore, (AKA: "The Barefoot Bandit"), Camano Island, WA.
In late June 2010, Colton was suspected of vehicle thefts stretching as far east as Illinois. The trail of suspected thefts attributed to him passes through Idaho, South Dakota, Nebraska, Iowa, and Illinois. Police found a 2008 white Toyota Sequoia in Norfolk, Nebraska, which was reported stolen in Yankton, South Dakota. Later that day, several burglaries were reported at Karl Stefan Memorial Airport, located 1 mile (2 km) south of where the SUV was abandoned. A truck owned by the town of Ottumwa, Iowa was later recovered in Dallas City, Illinois. On July 4, 2010, a Cessna 400 single-engine plane was reported stolen from the Bloomington, Indiana airport – it was later found crashed in the shoreline waters of Great Abaco Island in the Bahamas, again leading to speculation that Harris-Moore was responsible. Shortly afterward, there were several break-ins reported across the island. The Royal Bahamas Police Force placed wanted posters across the island that featured the teenager. One bartender claimed to have spotted him in a sports bar on Tuesday, July 6, 2010, stating that he drank a beer and left after five minutes. He says that Harris-Moore was wearing a cap over his shaved head and was barefoot.