Wilbur was born near Millville, Indiana, in 1867.

Orville in Dayton, Ohio, in 1871.

Both brothers attended high school, but did not receive diplomas. The family's abrupt move in 1884 from Richmond, Indiana, to Dayton, Ohio, where the family had lived during the 1870s, prevented Wilbur from receiving his diploma after finishing four years of high school. The diploma was awarded posthumously to Wilbur on April 16, 1994, which would have been his 127th birthday.

Orville dropped out of high school after his junior year to start a printing business in 1889, having designed and built his own printing press with Wilbur's help. Wilbur joined the print shop, and in March the brothers launched a weekly newspaper, the West Side News. Subsequent issues listed Orville as publisher and Wilbur as editor on the masthead.

In December 1892 the brothers opened a repair and sales shop (the Wright Cycle Exchange, later the Wright Cycle Company) and in 1896 began manufacturing their own brand.

In July 1899 Wilbur put wing warping to the test by building and flying a biplane kite with a five-foot (1.5m) wingspan.

In 1900 the brothers went to Kitty Hawk, North Carolina, to begin their manned gliding experiments.

The brothers flew the glider for only a few days in the early autumn of 1900 at Kitty Hawk. In the first tests, probably on October 3, Wilbur was aboard while the glider flew as a kite not far above the ground with men below holding tether ropes. Most of the kite tests were unpiloted, with sandbags or chains and even a local boy as ballast.

Hoping to improve lift, they built the 1901 glider with a much larger wing area and made dozens of flights in July and August for distances of 50 to 400 ft (15 to 122 m).

By 1902 they realized that wing-warping created "differential drag" at the wingtips. Greater lift at one end of the wing also increased drag, which slowed that end of the wing, making the glider swivel—or "yaw"—so the nose pointed away from the turn. That was how the tailless 1901 glider behaved.

From September 19 to October 24 they made between 700 and 1,000 glides, the longest lasting 26 seconds and covering 622.5 feet (189.7 m). Hundreds of well-controlled glides after they made the rudder steerable convinced them they were ready to build a powered flying machine.

With their new method the Wrights achieved true control in turns for the first time on October 8, 1902, a major milestone.

On March 23, 1903, the Wrights applied for their famous patent for a "Flying Machine", based on their successful 1902 glider.

In camp at Kill Devil Hills, they endured weeks of delays caused by broken propeller shafts during engine tests. After the shafts were replaced (requiring two trips back to Dayton), Wilbur won a coin toss and made a three-second flight attempt on December 14, 1903, stalling after takeoff and causing minor damage to the Flyer.

Following repairs, the Wrights finally took to the air on December 17, 1903, making two flights each from level ground into a freezing headwind gusting to 27 miles per hour (43 km/h). The first flight, by Orville at 10:35 am, of 120 feet (37 m) in 12 seconds, at a speed of only 6.8 miles per hour (10.9 km/h) over the ground, was recorded in a famous photograph.

In 1904 the Wrights built the Flyer II. They decided to avoid the expense of travel and bringing supplies to the Outer Banks and set up an airfield at Huffman Prairie, a cow pasture eight miles (13 km) northeast of Dayton. They received permission to use the field rent-free from owner and bank president Torrance Huffman. They invited reporters to their first flight attempt of the year on May 23, on the condition that no photographs be taken.

At Huffman Prairie, lighter winds made takeoffs harder, and they had to use a longer starting rail than the 60-foot (18 m) rail used at Kitty Hawk. The first flights in 1904 revealed problems with longitudinal stability, solved by adding ballast and lengthening the supports for the elevator. During the spring and summer they suffered many hard landings, often damaging the aircraft and causing minor injuries. On August 13, making an unassisted takeoff, Wilbur finally exceeded their best Kitty Hawk effort with a flight of 1,300 feet (400 m). Then they decided to use a weight-powered catapult to make takeoffs easier and tried it for the first time on September 7.

On September 20, 1904, Wilbur flew the first complete circle in history by a manned heavier-than-air powered machine, covering 4,080 feet (1,244 m) in about a minute and a half.

Their two best flights were November 9 by Wilbur and December 1 by Orville, each exceeding five minutes and covering nearly three miles in almost four circles.

The Wrights scrapped the battered and much-repaired aircraft, but saved the engine, and in 1905 built a new airplane, the Flyer III. Nevertheless, at first this Flyer offered the same marginal performance as the first two. Its maiden flight was on June 23 and the first few flights were no longer than 10 seconds.

The Wright brothers made no flights at all in 1906 and 1907. They spent the time attempting to persuade the U.S. and European governments that they had invented a successful flying machine and were prepared to negotiate a contract to sell such machines. They also experimented with a pontoon and engine setup on the Miami River (Ohio) in hopes of flying from the water. These experiments proved unsuccessful.

The Wright brothers wrote their 1903 patent application themselves, but it was rejected. In January 1904 they hired Ohio patent attorney Henry Toulmin, and on May 22, 1906, they were granted U.S. Patent 821393 for "new and useful Improvements in Flying Machines".

Their contracts required them to fly with a passenger, so they modified the 1905 Flyer by installing two seats and adding upright control levers. After tests with sandbags in the passenger seat, Charlie Furnas, a helper from Dayton, became the first fixed-wing aircraft passenger on a few short flights May 14, 1908.

Facing much skepticism in the French aeronautical community and outright scorn by some newspapers that called him a "bluffeur", Wilbur began official public demonstrations on August 8, 1908, at the Hunaudières horse racing track near the town of Le Mans, France.

Orville followed his brother's success by demonstrating another nearly identical Flyer to the United States Army at Fort Myer, Virginia, starting on September 3, 1908.

On September 9, he made the first hour-long flight, lasting 62 minutes and 15 seconds.

On September 17, Army lieutenant Thomas Selfridge rode along as his passenger, serving as an official observer. A few minutes into the flight at an altitude of about 100 feet (30 m), a propeller split and shattered, sending the Flyer out of control. Selfridge suffered a fractured skull in the crash and died that evening in the nearby Army hospital, becoming the first airplane crash fatality.

On October 7, 1908, Edith Berg, the wife of the brothers' European business agent, became the first American woman passenger when she flew with Wilbur—one of many passengers who rode with him that autumn.

The Wrights traveled to Pau, in the south of France, where Wilbur made many more public flights, giving rides to a procession of officers, journalists and statesmen—and his sister Katharine on February 15.

The Wright Company was incorporated on November 22, 1909.

On May 25, 1910, back at Huffman Prairie, Orville piloted two unique flights. First, he took off on a six-minute flight with Wilbur as his passenger, the only time the Wright brothers ever flew together. They received permission from their father to make the flight. They had always promised Milton they would never fly together to avoid the chance of a double tragedy and to ensure one brother would remain to continue their experiments. Next, Orville took his 82-year-old father on a nearly seven-minute flight, the only one of Milton Wright's life. The aircraft rose to about 350 feet (107 m) while the elderly Wright called to his son, "Higher, Orville, higher!"

There were not many customers for airplanes, so in the spring of 1910 the Wrights hired and trained a team of salaried exhibition pilots to show off their machines and win prize money for the company—despite Wilbur's disdain for what he called "the mountebank business". The team debuted at the Indianapolis Speedway on June 13.

The Wright Company transported the first known commercial air cargo on November 7, 1910, by flying two bolts of dress silk 65 miles (105 km) from Dayton to Columbus, Ohio, for the Morehouse-Martens Department Store, which paid a $5,000 fee.

Following a brief training flight he gave to a German pilot in Berlin in June 1911, Wilbur never flew again.

Before the year was over, pilots Ralph Johnstone and Arch Hoxsey died in air show crashes, and in November 1911 the brothers disbanded the team on which nine men had served (four other former team members died in crashes afterward).

Wilbur died, at age 45, at the Wright family home on May 30.

Orville succeeded to the presidency of the Wright Company upon Wilbur's death. Sharing Wilbur's distaste for business but not his brother's executive skills, Orville sold the company in 1915.

Orville made his last flight as a pilot in 1918 in a 1911 Model B.

On April 19, 1944, the second production Lockheed Constellation, piloted by Howard Hughes and TWA president Jack Frye, flew from Burbank, California, to Washington, D.C. in 6 hours and 57 minutes (2300 mi – 330.9 mph).

Orville died on January 30, 1948.

On November 23, 1948, the executors of Orville's estate signed an agreement for the Smithsonian to purchase the Flyer for one dollar. At the insistence of the executors, the agreement also included strict conditions for display of the airplane.

In October 1911, Orville Wright returned to the Outer Banks again, to conduct safety and stabilization tests with a new glider. On October 24, he soared for nine minutes and 45 seconds, a record that held for almost 10 years, when gliding as a sport began in the 1920s.