Preserving and Promoting Oakville's Heritage
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Phone: 905 844-2695

Guided Walking Tours

Step back in time with a stroll through historical Oakville!

Self-guided Tours are on another page. 
​
The Society has four Guided Walking Tours available for groups of six or more people. The price is $10.00 per person, with a minimum price of $60.00 for a Guided Walking Tour. The group may be smaller for the $60.00 minimum. No additional taxes.

These are arranged on a custom basis. If interested, please contact us. On the contact form, select walks. Other options are posted on on Contact page.

We hope our ever-popular Ghost Walks will return to normal this coming October.

For years we offered them on a scheduled basis but demand declined very suddenly and we switched to offering them by request only. If your small group, aka Social Bubble or Friend "of", is interested in one of these walks, we can set one up. Minimum six, maximum nine per walk. Our guides can maintain Social Distance.

​Our original walk is in the old part of 
town, between the Sixteen and Reynolds St, south of Robinson. Our Main Street Walk covers Lakeshore Road. The Trafalgar Road walk starts at St John's, goes north on Trafalgar to just below Cornwall Rd and back down Reynolds Street. Our newest walk takes us through Oakville St Mary's Cemetery. Each walk takes about 2 hours and costs $10 per walker. 
​
For groups of six to nine, 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:
  1. Oakville St Mary's Cemetery Walk;
  2. Old Oakville, Heritage Houses Walk in the old part of the town on the east side of the harbour;
  3. Main Street Walk and
  4. Trafalgar Road Walk from Randall St north to Spruce and back.
The cost is $10 per person. (All walks are cash only, payable at the beginning of the walk).

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.

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. Its border is in purple.

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 Guided Walking Tours.

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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  • HOME
  • Contact
    • DONATE
    • Internships
  • ABOUT
    • Our Story
    • Our Town
    • Our Downtown
    • Our Office and Grounds
    • The Thomas House
    • Our Interns
    • Our Sponsors
    • Our Plaques >
      • Plaque Process
      • Plaque Order and Payment
    • Supporting our Cadets
  • Publications and Resources
    • Newsletters
    • Reprints >
      • Beautiful Oakville - 1897
      • Garden of Canada - c1902
      • Telephone Book 1947
      • The Sumner Diaries
    • Audio Video >
      • Videos of Life in Early Oakville
      • Oakville Heritage Moments
    • Links
  • Collections and Exhibits
    • Archives, Photos and Libraries
    • Stories
    • Village Essays
    • Website
    • Basket Factory Memorial Plaques
    • War >
      • First World War
      • First World War Poppies Exhibit
      • Ontario Farmerettes
      • Munro Letters
    • Health Care As It Was >
      • Health Care As It Was - Continued
    • Oakville Images
    • Plaqued Houses and Buildings
    • Town of Oakville Online Collections
  • Membership
    • Join, Renew or Update
    • Why Be A Member
    • Our Volunteers
  • Activities
    • Speakers' Nights
    • Guided Walking Tours
    • Self-guided Walking Tours >
      • Downtown Oakville Historical Walk
      • Erchless Estate
      • Navy Street
      • Old Oakville
      • Trafalgar Road Heritage Conservation District
      • Trafalgar-Allan Corridor
      • Lot 12
      • Historic Reynolds
    • Black History Month
    • Indigenous History Month
    • Ghost Walks >
      • Survey
      • Photo and Video Submission
      • Photos 2022 Ghost Walks
      • Photos 2010 - 2022, Reviews 2016 - 2018
      • Reviews 2022 Ghost Walks
      • Volunteer for Ghost Walks
      • Ghost Stories
      • Video Ghost Stories
    • Doors Open
    • Culture Days
    • Historic Places Days
    • Yard Sale
    • Mayor's Historical Picnic
    • Family Activities >
      • Family Day
      • Annual Family Activities
      • Colouring >
        • Jigsaw Puzzles
  • Shop
    • Shop
    • Fine Art Prints
    • Shop Order Form
    • Art of Oakville
    • Payment