Toronto is home to a host of iconic businesses, but many of them are so ingrained in our experience of the city that we fail to appreciate just how influential and old they really are. It's not easy to keep a business prosperous through generational shifts and the radical transformation of consumer taste, but some enterprises have truly stood the test of time.

Here are 10 Toronto businesses that have outlasted the rest.

Henry's
Henry's was started as a jewellery store by Harry Stein in 1909, but by the late 1950s the company had shifted its focus to photography equipment. The location(s) at Queen and Church date back to the 1970s, which preceded the near closure of the business in the '80s only for it to storm back to prosperity during the digital age. There are now 28 locations in Canada.

Harbord Bakery
Wonderful smells have been wafting out of Harbord Bakery since 1929, making it one of the oldest bakeries in Toronto. Perhaps more importantly, it's been run by the Kosower family since 1945, who have used the same recipes for over 70 years at the Annex staple.

Hotel Victoria
The massive King Edward and Royal York might get all the attention, but the generally unheralded Hotel Victoria might be considered Toronto's original boutique hotel. It wouldn't have been considered small when it opened in 1909, but a major renovation in the 1980s brought the historic hotel back to life.

Kops Records
Founded in 1976, Kops Records has witnessed massive changes in the way that music has been consumed. None of the other record shops from the '70s heyday in Toronto remain in business, but thanks to the resurgence of vinyl, Kops is now up to three locations.

Glad Day Bookshop
The store has been forced to change locations over the year, but it remains the longest standing queer bookshop in the world. Established in 1970, the store pre-dates the official existence of the Pride Parade in Toronto and has served as invaluable community hub for over 45 years.

The Senator
One of the oldest restaurants in Toronto, the Senator dates back to 1929. The room hasn't changed a whole lot since then, and that's just fine with customers who flock to the old diner for staples like bacon and eggs and deli sandwiches served with a side of nostalgia.

Duke's Cycle
Founded in 1914, Duke's Cycle has been a fixture on Queen Street for a century. The store was driven away temporarily after a fire consumed the original location in 2008, but after a stint on Richmond, the shop returned to Queen West in 2011, where it expanded its footprint.

Curry's
Curry's first opened shop near Yonge and Bloor and has been a staple on the street ever since. The business has shifted focus over the years - from framing services to drafting materials for the aviation industry - but it's always broadly been about art supplies.

The Horseshoe
There are certainly older bars in Toronto (e.g. The Wheat Sheaf), but the Horseshoe gets the nod here for its continued relevance. From legendary bartenders to legendary Rolling Stones shows to being the key "my-band-has-made-it" stage in the city, the Horseshoe is as important today as it was when it opened in 1947.

Tom's Place
With the closure of Stollery's in 2014, Tom's Place immediately became the most prominent long-standing men's fashion retailer in Toronto. The shop has been a staple in Kensington Market since 1958, a period that's seen much of the rest of the Market turn over numerous times.

Thanks to Moosehead for sponsoring this post.

Photo by Tanja Tiziana in the blogTO Flickr pool.