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Toronto’s hip Ossington Avenue using events to attract visitors

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Ossington Avenue in Toronto is quickly emerging as one of the city’s most vibrant and sought-after neighbourhoods. TIME OUT magazine recognized Ossington in 2022 as one of the “coolest streets in the world.” The area has been booming ever since and has plans to continue to grow.

To increase foot traffic and encourage businesses to stay open later, Meg Marshall, the manager of the Ossington BIA, says they are having an event this week: the Raccoon pop-up shop where everyone who participates wins a prize. 

“Ossington has gone through some transformations and is starting to see a lot more destination retail and more destination hospitality popping up. We don’t have a lot of vacancies and any of the vacancies that were available are now being renovated into different spaces. We have seen a lot of West Coast brands open their first Toronto brick-and-mortar store on Ossington, and Ossington is a first for a lot of national brands, luxury national brands,” says Meg Marshall.

Ossington Avenue in Toronto. Photo: Ossington BIA

Raccoon pop-up shop – happening this week! 

Taking place on Ossington is the Raccoon pop-up shop which will be open only on September 5th and 6th. The event aims to increase foot traffic, boost brand awareness, and support local retailers.

The event invites visitors into a mini convenience store, complete with raccoon-themed decorations and interactive activities: “It is a mystery shop, you have to come to find out what we have.”

The pop-up will feature white-labelled products, all branded with raccoon imagery, which visitors can purchase. The event donates the food items to the Allan Gardens Food Bank, and each transaction results in a prize. Participants can win gift cards or small products from local shops.

“We have thousands of dollars in prizes we have purchased: gift cards, food products, small little products from our member businesses. So everyone’s a winner, and it all goes back to supporting our hyper local economy and encouraging people to go into the shops and restaurants.” 

Grassroots Initiatives

Due to a grant from Toronto’s main street innovation fund, the event was possible. Marshall says local volunteers and family members, such as her mom, helped with wrapping and branding.  

“We have wrapped close to 300 products with craft paper and then we are branding it, so this is a very grassroots initiative. We are not working with a marketing agency, we are doing it all ourselves and it has been really fun.” 

The main goal of this pop-up shop is to increase foot traffic on Ossington and aims to extend retail hours in the area as the shop will be open until 10 P.M. 

We want to drive more people to the retail shops, bring more people to Ossington, and extend retail evening hours as lot of retailers close at around seven or eight. The Raccoon retailer pop-up shop is staying open until 10PM, so it kind of leans into the night economy of Toronto,” says Marshall. “If everyone is staying open later, then it becomes a hub for customers to want to come to Ossington and creates it as a destination.

Community impact and future outlook

Marshall says the Ossington BIA is looking to continue to grow and bring more events to the neighbourhood.

The OSS Festival is another event happening yearly. The event takes place on the last Saturday of July every year and continues to grow.

OSS Street Festival on Ossington Avenue in Toronto. Photo: Ossington BIA

“We have been running this street festival for eight years, and it has evolved naturally as the retail mix and hospitality mix in Ossington has also changed. It originally started off as a bike race, and then we just found that it was cost prohibitive and also didn’t exactly support our member businesses, so we transitioned it into a street festival, and year over year – it keeps growing.” 

As Ossington moves forward, the BIA’s approach will likely involve a mix of small-scale, community driven projectors and larger events.

“We just hope that people continue to come out and support these initiatives because Ossington is really about community. We are small, but we are mighty. Everything we do is about bringing people together and celebrating what makes this neighbourhood so special. It is not just about the businesses; it is about the people, the culture, and the energy that makes Ossington what it is.”

Shelby Hautala
Shelby Hautala
Shelby Hautala is a Retail Insider journalist currently based out of Toronto. She has experience writing for local newspapers and also internationally for Helsinki Times while she lived in Finland. Shelby holds a Bachelor of Journalism Honours degree from the University of King’s College and a Social Work degree from Dalhousie University in Halifax.

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