the grandnephew of naval hero Commodore Oliver Hazard Perry was the 1st to fly across country, using IFR (I Follow Rails) to fly his Wright Brothers Model EX pusher biplane. October - November 1911 (thanks Steve!)

The publisher William Randolph Hearst had offered a US$50,000 prize to the first aviator to fly coast to coast, in either direction, in less than 30 days from start to finish.

In June 1911, Calbraith Perry Rodgers, 32 year old former football star, yachtsman, auto racer, and grandson of Oliver Perry (hero of the Battle of Lake Erie) a risk-taking sort of sportsman, was visiting his cousin John, a naval aviator, who since March was studying at the Wright Company factory and attending flying school in Dayton, Ohio.

 Rodgers became interested in aviation, took about 90 minutes of instruction from Orville Wright,  became the first private citizen to buy a Wright airplane, a Wright Model B modified and called the Model EX and in June 1911 before soloing, and had won an $11,000 air endurance prize in a contest in August.

Since the airplane would need a considerable support crew, Rodgers persuaded J. Ogden Armour, of meatpacking fame, to sponsor the attempt, and in return named the plane after Armour's new grape soft drink Vin Fiz.

 The support team rode on a three-car train called the Vin Fiz Special, and included Charlie Taylor, the Wright brothers' bicycle shop and aircraft mechanic.

The flight began at 4:30 pm, September 17, 1911, when Rodgers took off from the Sheepshead Bay Racetrack in Brooklyn, New York flying without instruments or navigational aids or maps, certainly no heater or other creature comforts, at a breathtaking (and time-consuming) 45 to 55 miles per hour.

To avoid the Rocky Mountains, he took a southerly route, flying through the Midwest until reaching Texas.

Although the plan called for a large number of stops along the way, in the end there were 75, including 16 crashes, and Rodgers was injured several times. Taylor and the team of mechanics rebuilt the Vin Fiz Flyer when necessary, and only a few pieces of the original plane actually made the entire trip.

On November 5, having missed the prize deadline by 19 days, Rodgers landed in Pasadena, California, in front of a crowd of 20,000. On the 12th he took off for Long Beach, California, but crashed at Compton, with a brain concussion and a spinal twist. He was hospitalized for three weeks. Finally, on December 10 he landed on the beach, and taxied the Flyer into the Pacific Ocean, completing the unprecedented journey of over 4,000 statute miles (6,400 km). Actual flying time totalled under 84 hours.

In 1986 the Vin Fiz flight was re-enacted in a replica to celebrate the 75th anniversary of the original journey.

http://www.aerofiles.com/vinfiz.html
https://en.wikipedia.org/wiki/Vin_Fiz_Flyer
https://en.wikipedia.org/wiki/Calbraith_Perry_Rodgers