This road enters Norwood at the railroad tracks north of Dana Avenue, traveling north through the heart of Norwood to the bridge over the old B.&O. Railroad tracks and the Norwood Lateral (SR-562), and then up the hill in a curving manner and continuing to Norwood's northern line and beyond.

The name probably came from the Village of Montgomery, through which the road travels. In early times, as a dirt road, it had other names. One of the earliest, for the part from Cincinnati through Norwood, at the time known as Sharpsburg, was the name "Cincinnati-Sharpsburg Road" or "Cincinnati & Sharpsburg Turnpike." The entire road was called Cincinnati, Montgomery, Hopkinsville, Sharpsburg, Rochester and Clarksville turnpike. Other names may have been the "State Road," the Cincinnati and Montgomery turnpike, Montgomery and Hopkinsville Turnpike Road, Montgomery Pike, Montgomery Boulevard and Main Avenue. Many "oldtimers" just call it "The Pike."

Starting as a dirt road connecting Cincinnati with parts of Ohio to the north, the section of Norwood became the central route through the city. A the village and city grew, the street developed into central business district. Over 100+ years, the street has been straightened, leveled, resurfaced by various methods and widened. In modern times the street became populated with business and multistory brick buildings. By the 1960s, urban renewal had started to drastically change the look and feel of the street. The changes continue to today, as most of the old buildings have been demolished, and shopping centers have replaced the "Main Street" experience.

It was started as a dirt road to provide a route from Cincinnati to parts of Ohio to the north. As maintenance was required, it became a turnpike, and users were required to pay a toll. The turnpike ownership became a sore spot, about the time Norwood was being incorporated as a village, when the growing populance desired a better means of travel to and from Cincinnati namely a street car line. With the county commissioners and State of Ohio's help, this "roadblock" to a modern commuter system was removed and an electric car track was built. One of the early riders of the street car remembered the road as having so many dips and hills, that it was like riding a roller coaster.

Bills were passed in Columbus relating to Montgomery Road. In 1892, Ohio House Bill No.96 attempted to take control of the road from private interest and give it to the county commissioners. However, this law may have been declared unconstitutional by the Ohio Supreme Court. The following year, Ohio Senate Bill No. 345, provided the county commissioners with the legal authority to widen, resurface and otherwise enhance the road from the Cincinnati limits, through Norwood and Pleasant Ridge, to Plainfield Road.

After Council approved a resolution to issue bonds to rebuild Montgomery Road on September 3, 1929, the citizens approved the proposition by a vote of 5,341 to 1,543 on November 4, 1929. Bids were let with the Gradison Construction Company the winner. The company started work on removing the exisiting granite block roadway on May 28, 1930, and completed the 4,250 feet long by 55 feet wide section in 99 days, much less than the 200 days allocated. The new road was built with reinforced concrete with a strength of 4,800 psi. Since street cars were still operating at this time, the rails were left in the street.

One of the early families of Sharpsburg, later Norwood, living on Montgomery Road was the Mills family. George E. Mills, son of Edward, became one of Norwood's mayors.

The residents and businesses on the entire Montgomery Pike in Norwood in 1896!