The initial townsite was oriented around the Maitland River, with the assumption that its water power and transportation opportunities would make it the focal point for development.

The form of the settlement soon changed, however, when the proposed Canada North-West Railway line was surveyed to the south of the village in 1858.

It would be over a decade until the railway finally did arrive, but in the meantime, the town had developed a number of typical pioneer industries, including a woollen mill, a tannery, and a foundry.

[3] However, the commercial centre of the settlement gradually shifted to Josephine Street by the 1870s, especially after the arrival of the Wellington, Grey and Bruce Railway in 1872.

[2] Wingham has a "complex railway history" as noted in a Historic Sites and Monuments Board of Canada report.

This branch line would ultimately be routed through Listowel, Brussels, Wingham, Lucknow, and Ripley on its way to Kincardine.

It had taken over the Toronto, Grey and Bruce Railway, whose abortive Kincardine branch had been terminated in Teeswater in 1874 due to competition from the WG&B.

[7] In 1885, the CPR announced that a stagecoach service would connect Wingham with a point on the Teeswater line known as Glenannon (or Glenannan),[8] where a small station was built.

[2] This was soon followed by the end of activity on the Canadian Pacific line, which was built with lightweight rail and had suffered washouts in the 1950s; the last CP freight customer, Wingham's Premium Forest Products, switched to CN in 1983 after CP built an industrial spur to connect it to CN's Kincardine Subdivision.

On April 9, 2007, it was announced that Rogers Communications had filed with the Canadian Radio-television and Telecommunications Commission to purchase all of the A-Channel stations, including CFPL, CKNX, CKX-TV, Access Alberta and several cable channels that were for sale by CHUM Limited in the wake of CTVglobemedia's acquisition of the CHUM group.

[15] Wingham was also served by a CBC English TV station (Channel 45), which re-transmitted CBLT-TV Toronto via CBLN-TV London.

The main thoroughfare is County Road 4, called Josephine Street within Wingham, which connects to London, Ontario to the south.

Wingham/Richard W. LeVan Aerodrome is a general aviation airport to the southeast of Wingham with fuel services and private hangars.

Wingham was served by scheduled bus service to London, Owen Sound, and Stratford until 2013, when provider Aboutown entered receivership.