Montgomery's own account made clear that he considered the technology of the second and third gliders of 1885 and 1886 as effective, but the airfoil designs were a disappointment in terms of lift-generation as they produced much shorter gliding flights in comparison to the first craft of 1884. He realized he was getting increasingly farther from understanding the mechanism of lift and began controlled laboratory experiments to investigate airfoils. In 1886 he briefly considered filing a patent caveat for lateral balancing, but did not.
About 1885 Montgomery began a long series of experiments with a whirling arm device, a smoke chamber, a water current table and large wooden surfaces angled into the wind in order to understand the physics of flow around curved surfaces. He also used dried bird wings placed in wind currents to observe the effect. His work in the 1880s confirmed that mechanical systems used by a pilot could preserve lateral balance and some degree of equilibrium in gliding flight. His experiments also confirmed the value of a cambered surface for obtaining lift.
In 1893 Montgomery visited the World's Columbian Exposition in Chicago, intending initially to attend a lecture by electrical expert Nikola Tesla. Upon arrival, he heard of the International Conference on Aerial Navigation to take place the first week of August. He introduced himself to Octave Chanute and Albert F. Zahm, who were collaborating in chairing the conference. He did not present a paper, but was subsequently invited by Chanute and Zahm to participate in the conference by giving two lectures of his own. His first focused on his experiments with surfaces in air and water currents. This talk was revised into an article and included in the conference proceedings. The article was later published in the July 1894 edition of Aeronautics. With encouragement from Chanute, Montgomery decided to give a second lecture. Although he refrained from providing enough detail that might be useful to designers, he did discuss use of hinged wing sections for lateral control. His second lecture was not published as part of the conference proceedings, because Chanute thought Montgomery wanted to seek patent protection. Instead, Chanute presented his own comments on Montgomery's flight experiments in his article series Progress in Flying Machines which was published serially in the American Engineer and Railroad Journal in 1893, and in the following year as a book of the same name. Montgomery reprised his second lecture in a talk to the Aeronautical Society of New York in 1910, and the contents were later published in several journals and books.
From 1893 to 1895, while teaching at Mt. St. Joseph's College in Rohnerville, California, Montgomery conducted further experiments into the physics of flow over a wing and lift generation using a smoke chamber and water table. From these experiments he developed a theory of lift based on vorticity, or what modern aerodynamicists refer to as a circulation theory or lifting-line theory. Montgomery compiled his results into a 131-page manuscript entitled Soaring Flight and attempted to have it published by Matthias N. Forney and the editors of Scientific American with the help of Octave Chanute. Chanute was reluctant to endorse it due to his disagreements with some of its theoretical content and suggested that it be edited to distinguish between experimental results and theoretical inferences. Scientific American rejected the manuscript, but later published an abstract. Chanute also directed one of his collaborators, Augustus Herring, to study the manuscript as he considered it instructive in understanding ground effect.
In 1884 Montgomery received a patent for a process to vulcanize and de-vulcanize India rubber. In 1895 and again in the period 1901 to 1904, Montgomery occasionally supplemented his aeronautical research with work in other branches of science, including electricity, communication, astronomy and mining. In 1895 he received four patents (American, German, British, and Canadian) for improvements in the efficiency of petroleum burning furnaces. In 1897 he took a teaching position at Santa Clara College and directed study of wireless telegraphy with Father Richard Bell. They were first to successfully transmit messages from Santa Clara College to San Francisco. Montgomery also patented two gold concentrator devices to assist miners in extracting gold from beach sands.
In early 1903 veteran balloonist Thomas Baldwin sought Montgomery's knowledge of aeronautics. Baldwin had also been assisting August Greth in constructing and experimenting with an airship (dubbed the California Eagle) at San Jose, California. Baldwin wanted improved propeller designs for dirigibles. He stopped working with Greth and came to Santa Clara College for an extended period to learn aeronautics from Montgomery. Their work together included wind tunnel tests at the college. At Baldwin's suggestion, they entered into a business arrangement in 1904 to make public exhibitions with manned Montgomery gliders launched at high altitudes from unmanned Baldwin balloons. By late May 1904, Montgomery made test flights with a new glider. However, Baldwin abandoned their collaboration and instead constructed his own airship (the California Arrow) at San Jose incorporating Montgomery’s propeller design and a 7-horsepower motorcycle engine (the Hercules of G.H. Curtiss Mfg Co.). The California Arrow would be first in America to make repeated circuits under control. During a protracted period of acrimony between Montgomery and Baldwin, Baldwin entered the California Arrow in the aeronautic competition at the St. Louis World’s Fair in November, 1904 and took first place.
In the fall of 1904 Montgomery conducted tests of his tandem-wing glider, the Montgomery Aeroplane, with associates Frank Hamilton and Daniel J. Maloney. On March 16, 17 and 20, 1905, in Aptos, California, Daniel Maloney made several successful flights in the glider at Leonard's ranch (Rancho San Antonio, now known as Seascape), after releasing from a hot-air balloon at high altitude. The resulting glides were well-controlled, and flights lasted up to 13 minutes. News of these flights received attention in both the U.S. and Europe. After this success, Montgomery gave a press conference to provide for the first time a history of his efforts in aeronautics and announced a patent application for his aeroplane. On April 29, 1905, Montgomery, Maloney, and Hamilton provided a public demonstration of the Montgomery Aeroplane, rechristened that day as The Santa Clara in honor of Santa Clara College. In view of hundreds of spectators and members of the press, Maloney released from the balloon at an approximate altitude of 4,000 feet above Santa Clara College. Maloney performed a series of pre-determined maneuvers and made a soft landing near the college grounds. This exhibition brought widespread recognition for Montgomery and was generally accepted as a milestone in aviation. In the following months Montgomery and Maloney made many exhibitions with The Santa Clara in the San Francisco bay area. On July 18, 1905 Maloney was killed when a rope from the balloon damaged the glider during the ascent, causing structural failure after release.
Following the catastrophic 1906 San Francisco earthquake, Montgomery’s gliding experiments were curtailed until 1911. Montgomery began experimenting with a new control system in which pitch and roll of the glider were managed by wing warping, while the tail assembly was fixed. Montgomery intended to add a motor and apply for a patent. This glider, The Evergreen (named after the region where flight tests occurred on the hillsides east of San Jose, California), was flown by Montgomery as well as another aeronaut Reinhardt more than 50 times in October 1911. On October 31 Montgomery was attempting to land at low speed and encountered turbulence, which caused a stall. He crashed and died at the site of his injuries. The hillside (now known as Montgomery Hill) is just behind Evergreen Valley College. John J. Montgomery was buried at Holy Cross Cemetery in Colma, California on November 3, 1911.
In 1946, Columbia Pictures released a full-length movie titled Gallant Journey based on John J. Montgomery's life and work. The film was directed by William A. Wellman, and starred Glenn Ford as Montgomery, Janet Blair as his wife Regina (née Cleary), whom he had married in 1910, and Charles Ruggles. The stunt pilots for the film were Paul Mantz, Paul Tuntland and Don Stevens. The film included several different historical reenactments of Montgomery’s glider flights. Gallant Journey premiered in San Diego, California on September 2, 1946 and had its full national release September 24, 1946. As part of the publicity for the movie, Columbia Pictures sponsored a cross-country Boston to Los Angeles tour featuring a 1911 vintage auto, the same vintage as Montgomery’s last flight. William Wellman had served previously in the U.S. Army Air Corps and was stationed as an officer at Rockwell Field, San Diego, California and Glenn Ford had also served in San Diego during World War II.
In 1945, the County of San Diego purchased 7 acres of land for the purpose of developing a monument to honor John J. Montgomery. By March 1946, this was expanded through the acquisition of 18 adjacent acres for the purpose of the development of Montgomery Park. The land acquisition process was led by Paul Mannen and Gordon Wiggins of the San Diego Junior Chamber of Commerce. Bob Wilson served as research chairman for the project, he later became a Congressman representing California's 41st District. On April 1, 1946, Regina Cleary, Montgomery's widow visited San Diego to review the location and planned monument.
The monument was designed by pioneering modernist Lloyd Ruocco. Around the monument base is a terrazzo walk with the names of aviators who followed Montgomery set into the stone. Set nearby is a tablet with an inscription to Montgomery's winged flight.
The Montgomery Memorial was officially dedicated on Sunday May 21, 1950 with John Montgomery's brother James Montgomery and sister Jane Montgomery in attendance. Robert Wilson was the Chairman of the Montgomery Memorial Committee, with William Brotherton serving as Master of Ceremonies. Jerome Rudrauff presented the Memorial as President of the San Diego Junior Chamber of Commerce. It was formally accepted by James A. Robbins, Chairman of the San Diego County Board of Supervisors
The Montgomery Memorial is recognized as a California Historical Landmark. It is also a Historic Landmark designated by the San Diego Historical Resources Board The Montgomery Park land originally acquired by the San Diego Junior Chamber of Commerce became the Montgomery-Waller Recreational Center in 1964 following the donation of another parcel of land next to the site by the family of Luckie Waller for a park named after her son. In the 1970s, an early hang glider Montgomery Meet was held on the hill near the Monument. In the 1970s another nearby recreation center was dedicated in the area as the Silver Wing Recreation Center.