The first hotel was a three-storey structure built by Sam Calvert in 1905, on almost the same location as the present hotel. Soon after the hotel was built it was followed by Gordon and Gordon's General Store, Henry Betin's Butcher Shop, Conrad Gach's Livery Barn, Flour and Feed, and A.E. Halberg's Blacksmith Shop. The first grain elevator was the Gillespie Grain Co., which remained in operation until the early 1990s. The first school was built in 1906, a one-room school located on the east side of the village. The first school trustees were John Ulan, Andrew Watson and James Kirkpatrick, and the first schoolteachers were Miss Doze and Mr. Moir. 

The second postmaster in Chipman was D.J. Simons who arrived in 1907 and left in 1909. After that, postmasters did not change very often. Mrs. Jennie McLennan had the position from 1909 to 1925. Mrs. Eunice Davies was postmistress for the next three years, and then George (Chappy) Chapman was postmaster from 1929-1946. John Motyka came next from 1946-1982 and presently the postmaster is Mrs. Carol Stribling. 

In 1913 Chipman was incorporated as a village, and the first councilors were Martin Wiltzen, John Kudrick, and Andrew Watson. By 1912 Chipman had a population of 175. There was one blacksmith shop, one chopping mill, one elevator, one hotel, two implement agents, one insurance office, two livery and feed stables, one lumber yard, one real estate office, two stock yards, three stores, a Methodist church, a school and a railway station. Land could be purchased for $12 to $25 per acre, and only 20% of the land was under cultivation. Chipman was becoming an important trade centre. Farmers from a long way to the north and east would bring their grain and livestock, and have their wheat milled into flour at the four mill owned and operated by Stafford and Garret. In winter one could look out to the north and see a long line up of teams waiting to unload. In 1915 a local of the United Grain Growers was organized. John Warshawski established a livestock buying station. When Canada entered into World War I many Chipman boys volunteered and saw service overseas. A local reserve unit of the 19th Alberta Dragoons, a mounted rifle unit, was formed and trained throughout the war. During the summers men and horses traveled from Chipman to Calgary for training at Sarcee. Casualty lists from overseas were awaited with dread, and before the cessation of hostilities in Europe, five local boys were killed, including R.E. Calvert, V.H. Junk, R.C. MacLennan, L. Sarah and B.S. Sipe. These names are inscribed on a monument made by stone mason, Frank Hisey which stood in the ball park just to the north of the recreation centre (curling rink) until recently when it was moved to Memorial Park, on Main Street.