Old Oakville Ghost Walks 2026: Two Ways to Explore After Dark

"Join ghost characters from the 1800s for family friendly fun and learning about Oakville's history, followed by light refreshments and discussions." That line comes from the Oakville Historical Society's Ghost Walks page, and it describes something that has run every October for years.

The 2026 season starts tomorrow, Tuesday, October 13. Downtown Oakville's business association is running its own version on the same streets this year, with a different meeting point, a different set of nights and a pub drink at the end. If you live close enough to walk to Navy Street, you can pick either one, and the choice comes down to which evening you want and how many seats are left.

A Cottage With a Blue Door, and Fifteen Places Per Walk

The Society's own walks begin and end at its offices at 110 King Street. You enter through the big white gates at the corner of Navy Street and King Street and follow the path to the cottage with the blue door.

This year's walks run daily from October 13 to October 30, except Sundays. Each tour lasts an hour, and there are two a night, at 6:30 p.m. and 8:00 p.m.

Each walk takes a maximum of 15 people. October 18 and 25 are Sundays, which leaves 16 walk nights. Sixteen nights with two tours each gives 32 walks, and at 15 people per walk that comes to about 480 places for the whole season. That's the total for a tradition the Society describes as running "in October each year."

The Society's booking rules are on the same page:

• Adults and teens 13 and older pay $15. Children 2 to 12 pay $8.
• Anyone under 18 must come with an adult, at a ratio of one adult to every four minors, and every accompanying adult needs their own adult ticket.
• You have to reserve in advance. Online sales close four hours before each walk starts.
• Tickets are first come, first served, and the Society says it cannot take waitlist requests.
• You can change or cancel for a full refund up to 48 hours before your walk, using the "Manage Tickets" link in your confirmation email.

With no waitlist, a sold-out 8:00 p.m. walk stays sold out. Your options are the 6:30 p.m. tour or another night.

Tuesdays and Wednesdays Get a Second Version

The Downtown Oakville BIA's Boos & Brews listing describes "a guided Ghost Walk through Downtown Oakville" with the Oakville Historical Society, followed by "a spooky drink at a participating restaurant." It runs only on Tuesday and Wednesday evenings, six nights in total.

Each night has its own pub:

Each pub gets two nights. If you already have a favourite among the three, the table tells you which two dates fit.

Tickets go through TicketPro, not the Society's own booking system. The TicketPro page lists each evening at 7:00 p.m. and gives the location as Market Square, 54 Navy St. That's a different start time and meeting point from the Society's 6:30 and 8:00 p.m. walks at 110 King Street. Go by the listing you bought from. The Boos & Brews ticket price wasn't shown on the TicketPro page we reviewed, so check it there when you book.

Here are the two formats side by side:

The Society describes its own walk as family friendly and caps it at 15. The BIA version ends at a pub on a weeknight. They draw on the same history but make for different evenings.

The Stories the Walks Have Told for Years

Neither listing publishes a route. The stories themselves are well documented, though. An InsideHalton feature on the Society's ghost walks recounted the tales guides have told while walking through downtown and the neighbouring heritage districts, including which homes of early politicians and business owners are said to be haunted. These are legends and reported sightings. The article doesn't claim to have verified any of them.

The family at the centre of it

The narrator in that feature was Robert Murray Thomas, played in costume, with actors as his parents, Merrick and Esther Thomas. According to InsideHalton, Merrick Thomas worked for William Chisholm, the shipbuilder regarded as Oakville's founding father. When Chisholm bought the land at the Sixteen Mile Creek in 1827, Merrick came to Oakville to oversee its development and the building of the harbour. He married Esther, the sister of Chisholm's wife Rebecca, and in 1829 acquired a farm that ran west of the creek from Lake Ontario north to what is now the QEW.

The family link explains why the stories reach from the harbour to Erchless. The guides are telling the town's history from inside its founding family.

Five sites, five legends

InsideHalton reported these stories from the walks:

1. Knox Presbyterian Church. The church stands on the site of an old tavern. One of the tavern's owners reportedly entertained customers by tying a bear to a pole and feeding it a live pig.
2. A house near the lake. This story centres on a piano stool that belongs with an upstairs room. When the stool was once lent out, the commotion upstairs reportedly stopped only after it came back.
3. The old stables. People have reported seeing ghost horses at a former stable that burned one night. The stable keeper died trying to get the horses out.
4. St. Jude's. Sightings have been reported in the church's belfry.
5. Erchless Estate. Nine different ghosts are said to haunt the estate, including Rebecca Chisholm, the former lady of the house.

The cast and the exact route may have changed since that feature ran. Most of these sites are a short walk from the white gates at Navy and King.

The Farmhouse That Still Stands at 144 Front Street

The Thomas story doesn't end with the walk. The farmhouse Merrick Thomas acquired in 1829 still stands. The Society says the Thomas House was built in 1829, contains original Thomas family items, and sits at 144 Front Street. InsideHalton reported that it stands in Lakeside Park because the Historical Society saved it from demolition in the 1950s.

So the family whose son narrated the ghost walk lived in a house the same Society later rescued. If you walk past Lakeside Park on any ordinary evening this fall, you're walking past the starting point of the founding story the tours tell after dark.

October 31 Moves to Towne Square

The Society's walks end on October 30. On Halloween itself, the downtown events happen in daylight.

From 10 a.m. to noon on October 31, the BIA lists Tiny Tots trick-or-treating at participating downtown businesses. At 1 p.m. the same day, Tails & Treats takes over Towne Square with dogs in costume, treats and a costume contest.

Old Oakville's October calendar runs in this order.

• Ghost walks every night except Sundays from October 13 to October 30.
• Boos & Brews on six of those nights, with a pub at the end.
• Daytime Halloween events downtown on October 31, starting with the youngest trick-or-treaters and ending with the dogs.

When the lights come back on Lakeshore, the next date on the BIA's calendar is Light Up The Night in Towne Square on November 20 at 5 p.m., with holiday lights, Santa and the annual tree lighting.

The ghost walks are built on the homes and buildings of Old Oakville's earliest families. If you own one of Old Oakville's heritage homes and want to know how its story and condition affect its value today, Robertson Kadwell would be glad to help. Request your complimentary home valuation.