During the first few decades of the twentieth century, Orange's dominance as a railroad center began to decline. Trains continued to stop in town through the 1930s, but the trains were rapidly being replaced with automobiles, which could be obtained from a number of Orange dealers. In 1906, there were approximately 600 automobiles registered in the State of Virginia with about 40 of these in Orange County alone. In 1910, the Orange Automobile Club was established and served as exclusive agents for selling autos. In February 1913, the club, renamed the Orange Automobile Company, opened a garage at the corner of Wall (Chapman) and Church streets and sold Ford, Reo, and Buick products. The company then changed owners and by 1920 was known as Roberts Brothers and sold Ford cars and trucks, Fordson tractors, and Oliver farm equipment. Other automobile dealers opened around Wall Street including Bates Brothers (1914), selling Dodge and Nash cars, and the garage of James Riley Macon and Manley Carter (1915) for Overland autos. Both of these dealerships had originally operated livery stables in Orange. Indian motorcycles were also sold in Orange by C.D. Quisenberry.
The popularity of the automobile soared in the next two decades. By 1930, there were over 373,000 autos licensed in the State of Virginia. The town of Orange became a regional center for automobile sales and service, perhaps due to its convenient location at the intersection of Route 15 and Route 20. Practically any make of automobile could be purchased in Orange at that time. Bates Brothers Motors sold Plymouths and Chryslers. Fords were sold by Orange Motors and W.C. Graham sold Hudsons and Dodges in a garage located on Madison Road.
Powell Motors, on Caroline Street in the building presently occupied by the James Madison Museum, sold Nash and Star autos. The parking lot behind the National Bank was the site of Ware Chevrolet Sales and Services. In total, there were 32 businesses in Orange County that dealt in automobiles and their accessories and many of them were located along the former Wall Street in the Town of Orange. Some of these dealerships still existed until recently. Reynolds Pontiac, Cadillac, and Suburu is Orange's oldest dealership under the same family management.
