The Southeastern Railroad, the South Eastern Lumber Company, and D. W. Biggs Lumber Company were the first non-mercantile businesses to locate here, opening the way for Ashpole to become the commercial center for lower Robeson County.

In 1899, the Union City Land and Improvement Company constructed the first tobacco warehouse and had N. G. Wade operate it. Ashpole Tobacco Warehouse sold 500,000 pounds of tobacco that year. J. D. Kyle began operating it in 1900 and continued in the tobacco business here until his death in 1933.

Sam Dunie and brother Harris opened a clothing store in August, 1900. Dunie had previously travelled through the village selling his wares from his cart but this season decided to open a store. Dunie's department store remained a fixture in the area for forty years.

O. I. Floyd took advantage of the railroad access to have Peruvian guano shipped in for sale to farmers. He also organized a cooperative to sell farm produce to northern markets. He also owned a furniture that he dubbed "The Store in Blue".

Justin Floyd, active in business since 1872 in the community, in 1903 began construction on a new building, the largest in town, at the northeast intersection of Red Cross and Main Streets. Fairmont Tire & Recapping is housed in half of the building, the other half being destroyed by fire in the December, 1915.

Evander McDaniel constructed two buildings in 1904, occupying one with his dry goods business and leasing the other to the newly-formed Bank of Ashpole.

Dr. John P. Brown became engaged in serious real estate development as he and I. M. Thompson constructed brick buildings for J. D. McLean & Company's occupancy in 1904. In 1905 three more were built, one owned by Brown and occupied by his Ashpole Drug Company.

A. B. Pittman opened the Fairmont Novelty Works, an iron and woodworking business in January, 1905. They also performed buggy and wagon repairs.