The Ottawa River, which drains into and out of Lake Timiskaming, has been a well-travelled route from the earliest times, including by Native peoples.

In 1886, Alexander H. Telfer led a survey trip up Lake Timiskaming and gave a report to the Temiskaming Settlers' Association.

William Ogilvie, who had recently distinguished himself by accurately surveying the Canada – Alaska boundary, led the expedition.

From the head of Lake Timiskaming, they proceeded north to James Bay, fixing accurate positions of the provincial boundary at regular intervals using geodesy data derived from star transits.

The settlers founded a prosperous agricultural center, taking advantage of the rich soil in the Little Claybelt region.

In 1901, Dymond Township was incorporated, and two years later in 1903, the Town of New Liskeard was established, with John Armstrong as its first mayor.

Farr encouraged settlement in the area, penning his own promotional pamphlet, entitled "The Lake Temiskamingue District", in an effort to attract new settlers to the region.

Marketed to settlers as prime agricultural land, Haileybury had only a handful of residents until the arrival of the Temiskaming and Northern Ontario Railway in the early 1900s, and the subsequent discovery of large silver deposits in neighboring Cobalt in 1903.

During the Cobalt Silver Rush, Haileybury became a 'bedroom community' that served the needs of the many miners and, most famously, many mine owners and managers.

Haileybury suffered the worst damage, and approximately ninety percent of the town was destroyed, leaving only Millionaire's Row and a few other neighborhoods intact.

[8] In more recent history, Dymond still functions largely as an agricultural centre, while the commercial and industrial interests in the area have mostly shifted operations to the former town of New Liskeard.

[10] A strong link to agriculture means that Temiskaming Shores has largely avoided the boom-and-bust cycle typical of most mining- and forestry-dependent small towns in Northern Ontario.

The Ontario Northland bus service makes scheduled stops in New Liskeard, Dymond and Haileybury.

The city's one enclosed shopping mall, Timiskaming Square, is located in the Dymond area at 883303 Highway 65 (47.51 N, 79.67 W).

Since then, large Walmart and Canadian Tire stores have been built nearby, resulting in a decline in mall business.

As of 2021, the mall only has 7 stores and services left: Food Basics, Dollarama, Giant Tiger, Pet Valu, TD Canada Trust, DriveTest, and Pop's Cannabis.