The Underground Railroad & Oakville

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The Underground Railroad & Oakville
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Nolan A Machan

Nolan A Machan

Nolan Machan is the Publisher of OakvilleNews.Org and has over 41 years of local Oakville knowledge. He is committed to providing Oakville residents with the most up-to-date information about our great town.

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From 1820 to 1865, the Underground Railroad secretly transported thousands of fugitive slaves who traveled from the southern U.S. across the border to freedom in Canada. For many escaped African Americans, Oakville harbour was their first view of Canada, the beginning of their new life of freedom, and the last stop on the Underground Railroad.

“People are absolutely amazed. They have no idea what a large part Oakville played in the Underground Railroad,” Bill Nesbitt, Museum Supervisor at the Oakville Museum at Erchless Estate

Oakville native, Captain Robert Wilson helped hundreds of blacks cross Lake Ontario on his ships. One individual, James Wesley Hill crossed the border in a packing box in the late 1840’s, settled on a farm near Oakville, and went on to help many escaped slaves by giving them work picking strawberries.

James Wesley Hill Also known as “Canada Jim” Alvin Duncan Heritage Collection

James Wesley Hill
Also known as “Canada Jim”
Alvin Duncan Heritage Collection

He sent his first earnings  back to his former owner as payment on his purchase price.

Hill first stayed with his friend Warren Wallace in Bronte. He became employed in Oakville by John Alton about 1850, to remove stumps and clear underbrush from a cleared wood lot. Hill rented a house from Alton and later rented the 100-acre Samuel Harris farm on 9th Line. He built a house which still stands today at 457 Maple Grove Drive. His strawberry farm helped to make Oakville a one-time strawberry industry capital of Canada.

James Wesley Hill made several trips back to Maryland, leading an estimated 700-800 African Americans to Oakville along the Underground Railroad. Hill’s reputation as a “Conductor” led to a price being put on his head, and in the United States he was wanted “dead or alive”.

Hill had married Adeline Shipley in Maryland in 1859. His children Ruth and Frank remained in Oakville throughout their lives, and neither married. Today James Wesley Hill’s memory continues to be honoured in Montgomery County, Maryland, where he was known as “Canada Jim”.

Oakville’s influx of newcomers led to integrated schools and church groups in addition to new businesses – there was a distinct change in the fabric of early Oakville society. Emancipation Day was celebrated in St. George’s Square. Freed slaves from all over Ontario returned to Oakville to remember the occasion and march up Trafalgar Road to Captain Wilson’s house (which still stands at 41 Navy Street).

Slavery was abolished in Canada in 1834. Oakville continues to celebrate it’s role in the emancipation of slaves and the underground railroad with a picnic held at Erchless. This year’s Emancipation Day Picnic is on Monday, August 5 from 1:00 to 4:00 PM.

 

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