Historical Walking Tours

The Society offers four walking tours exploring various aspects of Oakville's rich historical heritage:

Heritage Houses in Old Oakville:

This walk explores the homes of the Old Oakville Heritage Conservation District, Oakville's first such area. It includes many of the Town's oldest homes, some dating back to the late 1820s. Included are some interesting insights into the lives of Oakville's early inhabitants, such as their approach to "domestic downsizing".

This tour leaves from and returns to the Oakville Historical Society offices and archive at 110 King Street, Oakville, ON. Tea and light refreshments are served afterwards, providing an opportunity for informal discussion and viewing of archival displays at our offices.

Duration: about 2 hours.

The Guide for this tour is available on our Walking Tour Guides page. Questions? Please contact us.

Heritage Main Street of Old Oakville:

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 St. until its transformation starting in the 1950's.

Walkers will gather on the south-west corner of Lakeshore Road and Navy Street, east of the bridge over the creek (click here for map). 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 street is not a Heritage Conservation District, however many buildings have individual heritage designations.

Arrangements have been made for participants to gather at Second Cup after the tour for informal discussion and refreshments as desired.

Duration: about 2 hours.

The Guide for this tour is available on our Walking Tour Guide page. The Guide is updated annually and a printed version will be provided to all those participating in the walk.

Historical Walk of Trafalgar Road:

This walk explores the homes and other buildings of the Trafalgar Road Heritage Conservation District (and a bit more).

Take this walk prepared (and usually led) by a descendant of the Town's founder to gain insights into many of the lesser known aspects of Oakville's historical heritage: 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 - and Tim Horton's; the Underground Railway connection; 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, 262 Randall Street, where tea and light refreshments will be served following the walk.

Duration: minimum 2 hours.

A web version of the tour is available by visiting our Walking Tour Guides page and selecting the appropriate link on that page.

Ghost Walks

A few of the 9th Oakville Trafalgar Beavers - photo thanks to IndiraCelebrate Halloween by joining Society volunteers for a guided walk around the oldest part of the Town with an eerie spine tingling sensation and a dash of old Oakville history. Hear about some of Oakville's ghosts and haunted happenings. Perhaps you'll see a spirit or two on your walk!

Particularly well suited for children and youth groups such as Guides, Brownies, Cubs and Scouts.

These walks start at 110 King Street and tend to fill up. Book early to avoid disappointment.

Duration: about an hour.

Dates and Times of All Walks for 2013 will be posted when available.

Heritage Houses in Old Oakville - 2 pm
Main Street of Old Oakville - 2 pm
Trafalgar Road
2 pm
Ghost Walks
6 pm
7 pm



Tuesday 15
Thursday 17
  6 pm 7:15 8:30 pm
Saturday 19
Tuesday 22
Wed 23
Thursday 24
Friday 25
Saturday 26
Monday 28
Tuesday 29

Chost Walks are $12 per adult, children 12 and under, $6. Infants free.
Historical Walks are $10 per adult, children $5, Family $25.
All Walks are Cash only
, payable at the beginning of the walk.

Reservations are requested (so we can inform you of any last minute changes and avoid disappointments): 905-844-2695 up to the morning of the walk.  We do our best to accommodate those who show up at the scheduled start time without reservations, but the risk is yours!  We do cancel walks for bad weather. Your reservation will allow us to contact you.  
Ghost Walk Special Guests - Photo thanks to Indira
Reservations may also be made by email (click here), but not less than 3 days before the walk.

Special groups may be booked at other than scheduled times - like the 9th Oakville Trafalgar Beavers pictured at right.

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