Chipman was a thriving, bustling community by the end of the 1920s. After that, growth in Chipman began to level out and then decline. This reversal of fortunes was exacerbated by three events. The first of these events was the laying of the CPR line from Edmonton to Lloydminster, passing just ten miles north of Chipman. Although this was a boon to the farmers living as far away as the North Saskatchewan River, it was a blow to Chipman, for the new villages of Andrew and St. Michael drew a large proportion of the business which had previously gone to Chipman. 

The second and more dramatic event took place in 1931, when a disastrous fire started in Kuzyk's Store and spread to the drug store, garage, butcher shop, hardware and ultimately wiped out most of the business block lying on the east side of main street. The third event was more insidious, and affected not only Chipman, but all of America and the world. This was The Great Depression. Triggered in 1929 by the crash of the stock market, and followed by a drop in wages, loss of jobs, decline in prices, the depression was felt in every home. Grain and livestock prices fell so low that farmers could no longer make the payments on their farms, pay their taxes, buy machinery or even pay for their groceries. Businesses went under one by one, until the entrepreneurial spirit was virtually destroyed. Young men could no longer get jobs, and some rode the trains from city to city looking for work. Often when a freight train stopped in Chipman, numerous unemployed men scattered throughout the village looking for handouts of food. Seldom if ever were they refused, for most families shared willingly what they had, even if it was only bread and butter. To make things worse, the dry years came and lasted for most of the 1930s. 

But life went on in the town of Chipman. Around 1932 the first curling rink was built out of old lumber from a demolished elevator annex. It was a low, one sheet rink that was built, furnished and maintained by the local curling buffs. In 1939 many of Chipman's young people went off to war in Europe. After the war the complexion of the town changed once again, some did not return and others drifted away from the area or returned with different expectations. The economy had improved, and with the help of the veteran's allowances, they were soon launched into businesses, farming or more education. 

Just as an indicator of how depressed the economy had been, by 1946, there were only three telephones left in Chipman, and only one rural line with seven subscribers on it. Compare that with today's figure of over 300 telephones. 

The 1950s brought major improvements to Chipman. Northwestern Utilities extended their gas lines to serve Chipman with natural gas, a water and sewer system was installed and a new town office and fire hall were built. The Chipman School had been centralized to accommodate elementary and junior high school pupils from a wide area. In November, 1960, a bus-train accident claimed the lives of 17 local young people who were being bused to high school in Lamont. One of the highlights of the town's history came in 1978 when Queen Elizabeth II and Prince Phillip visited on an official tour. Large crowds gathered to greet her, and were thrilled to have her mingle and visit with them. The old railroad station was torn down, and a new park built in honour of her visit. A new subdivision opened up in the late 1970s and a number of new homes and a trailer court were constructed.

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