Street Festival Season! : Ossfest on Ossington Avenue

street festival toronto ossfest on ossington avenue between queen and dundas

With several choices of street festivals on any given weekend during these summer months, it's certainly the season to visit different neighbourhoods around town. On Saturday Nick and I took advantage of the few rain-free hours in the afternoon and headed over to Ossington Avenue to check out the second annual Ossfest, happening between Queen Street and Dundas.

I wrote about this area in detail last summer, (in this post), telling how that section of Ossington between Queen and Dundas is part of the oldest route into what is now Toronto. Back in the early 1800s, when Toronto was no more than a fort and a trading post, the main path through the woods from the west, included that stretch. Of course, the buildings came later, around the mid to late 1800s, but they were built right along that original path.

Luckily, many of the historic buildings are still there, home to a number of great indie shops, restaurants and bars that line the street. Many people, including us, usually go there for the fun and bustling nightlife, making this daytime look fresh and interesting.

There was a variety of things to see and do at Ossfest, including a stage for live music, different booths, activity areas, shops with special sales on, bars that are normally closed during the day, and restaurant food-stands.

We walked up to Dundas from Queen Street West, and then turned around and walked back down, which is why these photographs are taken from different directions.

parlour salon ossington avenue toronto at ossfest street festival

↑ People were clearly enjoying this booth where stylists from Parlour Salon had their chairs outdoors. ↑

parlour salon doing hair outdoors at ossington street festival toronto


↑ I rarely include pictures of small children who I don't know on these pages, however I can't resist posting this one I got by chance, when randomly shooting the basketball training area. ↑

ossfest ossington avenue street festival toronto

Reposado Tequila Bar on the right, is a place I'll always especially appreciate because it's where I first met one of my best friends.

They have a great patio outback, which was open for daytime hours thanks to the festival. ↑

line up at bang band icecream ossington avenue toronto

Bang Bang Ice Cream always seems to have a line-up, festival or not. Must be very good. ↑

bellwoods brewery ossington avenue toronto

Bellwoods Brewery is another place that's always busy. ↑

stage at ossfest street festival ossington avenue toronto

↑ There was a stage set up at the north end of the festival, with a full schedule of live music. The Tonkas were on stage. ↑

From there we turned around and walked back down.

This bar, Man of Kent, is usually a nighttime venue, but was open for Ossfest. Its lovely interior, as viewed through the open door, seemed to call us in for a beer.

man of kent bar ossington

The menu listed a bunch of delicious sounding sandwiches, so we decided to try one -- Nick ordered the bbq chicken with jalapeno cheese and kale sandwich, and I the Falafel Tahini Wrap, which contained chickpeas, sweet potato, lemon tahini sauce and pickled Ontario vegetables. Then we noticed that there wasn't a kitchen, so wondered what we'd get.

The food turned out to be very good, (so good, in fact, that Nick repeated that he liked his sandwich later, as we walked home!). I asked the server about the food and he said they got it from Foodbenders, a catering company with a shop at 1162 Bloor Street West, but who also supply quality healthy food made with locally sourced ingredients, to cafes and bars. All the bar had to do was quickly heat up the sandwiches in a press. Such a great idea!

man of kent bar toronto ossington avenue

beer and food

bar and flowers

man of kent bar ossington avenue toronto

We enjoyed our time at "Man of Kent" and were glad we went in. If not for the festival and their decision to open for it, we might never have discovered it.

omaw restaurant outside historic building on ossington avenue toronto

↑ This old building is named "LeVack Block" and was built in 1891. It's a restaurant now, called Omaw, which wasn't open when we passed. ↑

n and l

old buildings ossington avenue toronto

ossington avenue street festival toronto ossfest

places on ossington

street and do goodys emporium at ossington avenue street festival toronto

↑ This booth of handmade cute children's clothing was operated by volunteers from Do Goody's Emporium, who give all profit vulnerable Children in Africa & Canada. ↑

new building ossington avenue toronto and lulu lemon pop up for men

↑ As mentioned, many of the lovely historic buildings remain on Ossington, however, there is new development going on too. ↑

painted building on ossington avenue toronto

oysters ossfest street festival ossington avenue toronto

↑ Butcher Cote de Boeuf, further down the street, were shucking oysters for the occassion. Although they are a meat shop, I see on their site that in the evening from Wednesday to Saturday and all day Sundays they open for a special "bar á vin" where they serve wine and beer, French cheeses, charcuterie and oysters. ↑

One thing I noticed about this part of Ossington street that I wasn't aware of, is that it is a good place for shopping for mens' clothing. There were several stores featuring very nice things. They were crowded and Nick wasn't in the mood to shop, but we'll go back sometime to get him something.

tiger of sweden mens clothing shop on ossington avenue during ossfest

Tiger of Sweden offers clothes for men and women. ↑

outside lost and found mens clothing shop ossington avenue toronto

Lost and Found for mens' clothing, at 44 Ossington Ave, was a popular spot! ↑

guitar player joseph piilonen

↑ Excellent solo guitar playing by Joseph Piilonen. ↑

historic building and hello mural on ossington avenue toronto during ossfest

ossington avenue toronto street sign

We got back down to Queen Street just as more rain began to fall. At home later, we listened as it poured down, doing its best to ruin the rest of this outdoor festival. I'm sure people still had a good time though, in spite of the rain, by moving into one of the many bars and restaurants along this cool and vibrant street.

Thanks for reading,
xo loulou

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2 Responses to Street Festival Season! : Ossfest on Ossington Avenue

  1. Our town tries to do something like this ever year called Railfest. About two years ago they called out everyone and everything to set up some kind of booth at the last minute for free and it was SO awesome! It was so lively and busy! I guess my town hates success because they didn’t do it again after that and now it’s back to being the same ol “shop the plaza” and listen to bad music deal.

    • Loulou says:

      Hi Hollie. Here, many of the street festivals tend to be food-centric, which I don’t really get, because once you’ve eaten, then what? So, yes, this was a good one thanks to the variety of things going on. Maybe you should take on organizing Railfest II! Lol, like you have so much time. :)

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