Hogg's Hollow is named after James Hogg, a Scotsman from Lanarkshire, who settled in the area in 1824. Hogg operated a whisky distillery and a grist mill, and was considered the most successful of all the millers in the valley. In 1856, James Hogg's sons John and William subdivided their late father's estate under the name "Hogg's Hollow". The Hogg's Hollow subdivision included one hundred and forty-one lots, however only a handful of houses were actually built at this time.

Four of the original Hogg's Hollow houses are still standing. These include two former mill workers cottages that were relocated in 1986 to 4150 Yonge Street, where they now serve as the entrance to the Auberge du Pommier Restaurant. The other two original houses are located at number one and number five Old Yonge Street. Both of these houses have undergone extensive renovations. The Jolly Miller tavern, circa 1857, situated at 3885 Yonge Street, and the George S. Pratt House, circa 1886, located at 17 Mill Street, are the other historic landmarks in this neighbourhood.

The present day Hogg's Hollow neighbourhood began to be subdivided in the 1920's. The neighbourhood grew in stages and was finally completed in the 1960's.