Step back in time with a stroll through historical Oakville!
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For groups of eight or more, we’re pleased to offer Live Guided Walking Tours throughout old Oakville.
Our insightful and engaging tour guides will delight you with a glimpse into the history of key landmarks and facts on previous property owners. We can also include tea and light refreshments served afterwards at our offices. Our tours make great company outings and school trips! More details on the following four walks are below:
Please contact us at least two weeks in advance. For individuals and small groups, just ask about pricing.
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Guided Walking Tour of Old Oakville
This tour explores the exterior of the homes in our Old Oakville Heritage Conservation District, Oakville's first area of this kind. You will be able to appreciate many of the Town's oldest homes, some dating back to the late 1820s. Our lively tour guides will delight you with interesting insights into the lives of Oakville's early inhabitants, such as their approach to "domestic downsizing".
The tour leaves from and returns to the Oakville Historical Society offices and archive at 110 King Street, in Oakville, Ontario
Duration: about 2 hours, if following the guide.
Book your spot to learn more when you take this guided walking tour. If using the contact form, select Walks.
The tour leaves from and returns to the Oakville Historical Society offices and archive at 110 King Street, in Oakville, Ontario
Duration: about 2 hours, if following the guide.
Book your spot to learn more when you take this guided walking tour. If using the contact form, select Walks.
Self Guided Walking Tour of Old Oakville
Purchase a copy of The Walker’s Guide to Old Oakville (2019) for $5.00
Contact us to pick up your copy.
Contact us to pick up your copy.
Guided Walking Tour of Old Main Street
This walk covers the original business section of the town which has extended since the 1830's from the Sixteen Mile Creek to Trafalgar Road. From that point eastward, the street was mainly residential to Allan Street until its transformation starting in the 1950's.
This tour starts on the south-west corner of Lakeshore Road and Navy Street, east of the bridge over the creek (click here for map) in Oakville, Ontario. From Navy Street, the tour proceeds along the south side of Lakeshore Rd. to Trafalgar Rd. to view the north side, returning on the north side to view the south.
(The Downtown Oakville Heritage Conservation District went into effect on March 9, 2013. Its irregular shaped border includes Lakeshore from west of Navy Street to Dunn Street).
Duration: about 2 hours, if following the guide.
Book your spot to learn more when you take this guided walking tour. If using the contact form, select Walks.
This tour starts on the south-west corner of Lakeshore Road and Navy Street, east of the bridge over the creek (click here for map) in Oakville, Ontario. From Navy Street, the tour proceeds along the south side of Lakeshore Rd. to Trafalgar Rd. to view the north side, returning on the north side to view the south.
(The Downtown Oakville Heritage Conservation District went into effect on March 9, 2013. Its irregular shaped border includes Lakeshore from west of Navy Street to Dunn Street).
Duration: about 2 hours, if following the guide.
Book your spot to learn more when you take this guided walking tour. If using the contact form, select Walks.
Guided Walking Tour of Historical Trafalgar Road
You may find this to be your favourite walking tour! This historical walk of Trafalgar Road explores the homes and other buildings of the Trafalgar Road Heritage Conservation District (and a bit more).
Our most comprehensive tour, this walk provides fascinating insights into many of the lesser known aspects of Oakville's historical heritage such as Trafalgar, a wood plank toll road; the Great Fire of 1866 that sent flaming kerosene all the way down the Sixteen to the harbour; the connection between the Temperance movement; the Underground Railway connection; and The Hamilton Radial Railway....
Because of the distance covered, a comfortable pair of walking shoes is recommended.
This tour starts and ends at St. John's United Church, at 262 Randall Street in Oakville, Ontario.
Duration: minimum 2 hours, if following the guide.
Book your spot to learn more when you take this guided walking tour. If using the contact form, select Walks.
Our most comprehensive tour, this walk provides fascinating insights into many of the lesser known aspects of Oakville's historical heritage such as Trafalgar, a wood plank toll road; the Great Fire of 1866 that sent flaming kerosene all the way down the Sixteen to the harbour; the connection between the Temperance movement; the Underground Railway connection; and The Hamilton Radial Railway....
Because of the distance covered, a comfortable pair of walking shoes is recommended.
This tour starts and ends at St. John's United Church, at 262 Randall Street in Oakville, Ontario.
Duration: minimum 2 hours, if following the guide.
Book your spot to learn more when you take this guided walking tour. If using the contact form, select Walks.
Interested in a self-guided walk? Explore the Erchless Estate
For a charming self-guided tour you may wish to see the Erchless estate, home of the Chisholm family from the early 1830’s until the 1960’s. After standing empty for several years, the estate was acquired by the Town of Oakville for $550,000 in the 1970’s.
The cottages are now the offices of the Oakville Historical Society.
A complimentary pamphlet about this walk is available for pick up in our office.
The cottages are now the offices of the Oakville Historical Society.
A complimentary pamphlet about this walk is available for pick up in our office.
Guided Walking Tour of St. Mary's Pioneer Cemetery
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This Tour might be offered again
Love history? Join us on a guided tour of Oakville and St. Mary's Cemeteries led by community experts from the Oakville Historical Society. Learn about local historical events, unique carved symbols and their meanings, and some of the town's earliest settlers. The cemetery lands were donated by Oakville's first mayor in 1858 and is the resting place of Oakville's founder, Colonel William Chisholm. Please meet at the cemetery entrance at 659 Lyons Lane. Rain or shine. Required preregistration is now closed for a maximum of 15 participants. This walk may be offered again. |
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This tour covers the history of St. Mary's Pioneer cemetery, an Ontario Heritage Act historic site and the burial place of Oakville's founder, Colonel William Chisholm.
You will learn about the cemetery's 1858 origins when the land was donated by the first mayor of Oakville, George K. Chisholm. Interestingly, the land was surveyed by George C. Tremaine, whose Map of Halton County, Canada West appeared the same year. After clearing the trees, the land was surrounded by a white picket fence and a line of hitching posts was placed on Sixth Line. Pines that still exist in the cemetery today were planted along the road. A sale of lots was held at Town Hall and those purchased were marked with little white stakes bearing the names of the owners. Chisholm suggested the old cemetery on Reynolds Street, north of Palmer Avenue, be moved to the new town cemetery to make way for a public school. This necessitated the removal of remains from the old cemetery over the next 20 years, creating considerable interest among the residents at the time. |
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