Night on the Old Town: A Historic Tale of Hotels & Taverns

People have always enjoyed a little cheer with their food, and Oakville and Burlington have provided both to our community for almost 200 years. Of course, the past holds secrets and surprises, so letโ€™s look back and see what we find.

ย The idea of animal entertainment isnโ€™t new, but the variety provided by one of Oakvilleโ€™s most infamous taverns wouldnโ€™t fly today. Thomas Lloyd kept a bear chained outside his tavern on Dunn Street and when business was slow, the bear would be fed a live pig to both excite and attract customers!

Oakville House, the townโ€™s first inn, was more respectable. Owner William Sumner boasted that he offered โ€œbeds [that] are clean and comfortable โ€“ a larder well stored [and] good liquors purified by Ontarioโ€™s beautiful waters.โ€ This building too has a bear in its origin story. Legend tells that during construction, local dogs treed a bear nearby. That bear faced a different fate as it soon became a rug to adorn the floor in front of the main fireplace.

When well-known writer Anna Jamieson visited Sumnerโ€™s Inn in 1837, she was not impressed by the โ€œvile printsโ€ on the walls but was amused to find a copy of Don Juan in the parlour, a most sophisticated and modern addition. Sumner also hosted the to-be Lieutenant-Governor Sir Francis Bond Head, who โ€œobserved that it was the best tavern he had been to since leaving Albanyโ€.

The Oakville House remained a fixture until the 1950โ€™s when it was demolished – but only after surviving an astonishing seven fires! Luckily the tradition of good food continues today, as the building that houses Paradiso stands in that spot.

In 1896 The Toronto Cycling Club had a track built from Toronto to Oakville, and the Queenโ€™s Hotel at the corner of Dunn and Colborne billed itself as the โ€œHeadquarters for horsemen and bicyclistsโ€ – hoping to attract the thirsty โ€œwheelmenโ€ after their races.

Heading West, the oldest hotel remaining in Oakville sits at Navy and Robinson Streets. It began as the Canadian Hotel in 1857, but became the Murray House in 1896. Now restored as offices, this handsome building is worth taking a minute to admire.

In 1845, adventurers continuing along the lake road would come to Thompsonโ€™s Hotel in Bronte. Over the years, the site was a grocery store, candy shop, post office, and a summer hotel! Named โ€œGlendellaโ€ since 1887, it has recently been restored and is in use as boutique suites.

Today you can stroll around the corner to the Cove Bar and Restaurant, a trendy spot inhabiting an original 1840โ€™s house. By 1900 a family of fishers lived here, making the prevalence of fish on Coveโ€™s menu seem historically appropriate.ย 

Steady your legs as we hop on the stagecoach to Burlington, where you could linger at โ€œthe Zimmerman house โ€ฆ a first-class resting place for The weary traveller.โ€  Later it became the Queenโ€™s Hotel, and today the same spot is The Queenโ€™s Head, which operates as a classic British Pub.

On the waterfront stood the Estaminet Standard Hotel, managed by Emma and George Byrens. In 1919, โ€œCanadaโ€™s House of Hospitalityโ€ served notables from Louis St. Laurent to Liberace! Emma would greet patrons accompanied by her parrot. The venue lived on to become the well-known Emmaโ€™s Back Porch named in her honour.

Our final stop is the once fabulous Brant Inn. In the 1940โ€™s, people came to dance the night away with Louis Armstrong, Ella Fitzgerald, Benny Goodman, and Count Basie. Demolished in 1969, only a plaque now sits on the site. But donโ€™t despair, nearby Spencer’s at The Waterfront affords dining with virtually the same lovely view of the lake.

The names may have changed but you can still have an excellent food and drink adventure while retracing the steps and places in our local hospitality history.

Julian Kingston has deep experience interpreting culture, art, history and the natural world. He currently takes care of the Oakville Museum at Erchless Estate, exploring as many ways as possible to tell Oakville’s stories. You should totally go.

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