Sixteen Hollow - 1820-1880: by Judith Bourke

Settlement in the Township of Trafalgar began soon after the Mississauga Purchase in 1805. After this large area from Burlington Bay to the Etobicoke River was surveyed in 1806, Dundas Street, surveyed originally in 1795 ¹, was opened up. One of the duties of the first settlers was to clear the road allowance on their property. For this reason, pioneer settlement was particularly encouraged along Dundas Street. In order to get the road cleared as quickly as possible, the settlers undertook to do the work in eighteen months instead of the usual two years allowed ². The road was very rough, but however bad this road was, it was an important link to York (Toronto) which gave a head start to settlements along its route.

Robert Gourlay's Statistical Account of Upper Canada lists one grist mill and four saw mills in Trafalgar Township in 1817 ³. On a bend of Sixteen Mile Creek, north of the Smith-Triller Viaduct on Upper Middle Road, the remains of well-made banks and ditches clearly point to a mill site. This site lies across what were Lots 20 and 19 South of Dundas Street (SDS). While the owners of these lots were not assessed for mills, Philip Triller was. ⁴ Triller, known to be the owner of the first mill in Trafalgar, owned Lot 21 SDS and, with his sister Catherine, 61 acres of the north part of Lot 22 SDS ⁵. The assessment of 1818 lists Philip Triller as owner of a mill on Lots 21 and 22.  Over the next few years, the assessments show that he had a sawmill and a grist mill that eventually had two run of stones. Triller's property on Lots 22 and 21 had no easy access to the creek; his mills must have been sited on his neighbours' property to the east.

Samson Howell (Triller's brother-in-law and neighbour on Lot 24 SDS) had a letter from his father in New Jersey in November of 1816 who wrote. "Was glad to hear you had a mill built near you." ⁶ From this it would seem probable that the mill was built in 1815 or 1816.

Unfortunately for Triller, in 1827 George Chalmers, who first appeared in the assessment rolls in 1825 on Lots 22 and 23 NDS with a merchant shop, built a dam on the Sixteen north of Dundas Street to run both grist and saw mills. By 1830 Triller was operating only the saw mill and by 1833 this too was gone.

George Chalmers saw great potential in the power of Sixteen Mile Creek and invested heavily in land and industry in the settlement at Dundas Street, which for a while was known as Chalmers' Mills. In addition to the mills and shop, he had a storehouse, up to six houses, an ashery, a distillery, a tavern with barns, a blacksmith's shop, and other buildings as well as hundreds of acres of land. ⁷ Chalmers was a Colonel in the militia and he and his troops were called out during the Mackenzie Rebellion in 1837. A tale was told that when William Lyon Mackenzie was evading capture by Chalmers' militia after the incident at Montgomery's Tavern, he hid in the attic at Triller's farm while Triller's seven young daughters "entertained with food and drink the soldiers who were searching for him". ⁸ In his own thrilling account of his escape "hotly pursued" by the militia, Mackenzie only relates that Colonel Chalmers had posted guards at the bridge over the Sixteen and the creek had to be crossed. "We accordingly stripped ourselves naked and in a bitter cold December night, buffeted the current, and were soon up to our necks." This painful crossing of the icy creek was apparently made above Chalmers' dam. ⁹

During the 1830s Chalmers continued to buy property, including three lots in the New Survey of Oakville, but as the decade drew to a close, he began to have financial difficulties and became bankrupt. In 1840, he had already lost the mills, shop and storehouse ¹⁰ and it was necessary to sell 400 acres of land, the distillery and other buildings. By 1844 John Proudfoot was the owner of the mills, and the village became known as Proudfoot's Hollow. ¹¹

The 1850s were prosperous in the Hollow. A three-storey inn catered to the stagecoach trade along Dundas Street, and a tannery, ¹² carding mill and a steam stave mill were added to the earlier industries. In 1850, the inn served as the polling station for the first election of officers for the Municipality of the Township of Trafalgar. ¹³ Many small tradesmen and artisans had shops in the village including weavers, shoemakers, a wagon maker and a tailor. ¹⁴ There was a school at the top of the road on the west bank, ¹⁵ and the Knox Sixteen Presbyterian Church was built on the east bank in 1846. ¹⁶

After its brief boom, the village began to decline in the 1860s. There were several reasons for this. The railroad took much of the traffic away from Dundas Street, the grain market collapsed at the end of the Crimean War, and the big timber was gone. The inhabitants began to leave the village and Proudfoot sold his holdings and moved to Cleveland, Ohio. ¹⁷ By the 1880s only two houses remained occupied and the big three-storey mill closed down.

The journey to the village at the foot of the steeply sloping sides of the ravine was notoriously dangerous. The inn must have done a roaring trade with drivers of stagecoaches, drays and other vehicles coming in to calm their nerves after a hazardous descent and to fortify themselves for the coming ascent. The metal 88-foot (26.8 m) bridge built in 1885 was the first dependable bridge to carry Dundas Street over Sixteen Mile Creek but came too late for the villagers. It served well until the first concrete high-level bridge spanned the ravine in 1921, an engineering marvel which people came from miles around to see. The old tortuous road was finally closed in 1922. ¹⁸ In 1960 ¹⁹ the 1921 bridge was in its turn superseded by the present four-lane bridge, but the piers of the earlier bridge remain. Now in 2008, the bridge is again undergoing reconstruction with new piers built on the same line as 1921.

After he lost his property in the Hollow, Chalmers became the MP for East Halton in 1844 and, sadly, after being defeated in 1848, committed suicide in June of that year. ²⁰ At 80 years of age, Philip Triller died in 1866 at Wellington Square (Burlington) from injuries suffered in a buggy accident on his way to Smithville to celebrate his birthday at the house of one of his daughters. ²¹

Footnotes

1. Ontario Ministry of Transportation Publication; History of Ontario Highways: From Footpaths to Freeways.
2. Mathews, Hazel C., Oakville and the Sixteen (Toronto: University of Toronto Press, 1971), 5-7.
3. Gourlay, Robert, Statistical Account of Upper Canada (Wakefield, Yorks: S.R. Publisher, 1966), 402.
4. Trafalgar Township Assessment Rolls, 1818-1833. The lot numbers are not shown on the earliest assessments, and the columns are badly drawn leading to ambiguity in the type of mill.
5. Land Transfer Abstract Index, Trafalgar Township, 1 SDS, Lots 18-35.
6. Howell Family. Typescript copy of letters. Hamilton Public Library.
7. Mathews, Oakville and the Sixteen, 181; Trafalgar Twp. Assessment Rolls, 1825-1840.
8. Clarke, Gwen, Halton's Pages of the Past (Acton; Milton: Dills Printing & Publishing, 1955), 20.
9. Lindsey, Charles, The Life and Times of Wm. Lyon Mackenzie, (Toronto: P.R. Randall, 1862) 2 v. in 1, v. 2, 108.
10. Trafalgar Twp. Assessment Rolls, 1840.
11. Mathews, Oakville and the Sixteen, 181.
12. Land Transfer Index, Trafalgar Twp., Lots 18-35. The 1871 will of Samuel Bowman mentions "Tannery Dwelling Houses and Tannery plant on said lot". Samuel Bowman and his partner Clayton owned part of Lot 23 SDS from 1829.
13. Mathews, Oakville and the Sixteen, 294.
14. Clarke, Halton's Pages of the Past, 17.
15. Tremaine, George, Tremaine's Map of the County of Halton, 1858.
16. Information provided by Rev. G. Walter Read, Knox Sixteen Presbyterian Church, October 2000.
17. Mathews, Oakville and the Sixteen, 181.
18. Clarke, Halton's Pages of the Past, 17,20.
19. Information provided by the Ontario Ministry of Transportation.
20. Archives of Ontario, Surrogate Court Records. MS 638, Reel 43.
21. Inscription of headstone at Knox Sixteen Presbyterian Church; Canadian Champion, 21 June 1866, page 3, col. 1.