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Three Day (Winter) Toronto Trip

We went to Toronto over Thanksgiving since we both had time off of work. Our airbnb was on Queens street in the Fashion District. We loved this location – it was near a bunch of bars, restaurants and shops. We were only a short walk from a lot of sites. And there was free overnight parking on a few blocks nearby.

We tried to choose places that would keep us warm in the cold November weather.


Fahrenheit Coffee: We stopped here to start our day and this place was crazy! Everyone was dressed in costumes and they were all going insane when we walked in. It was the store’s birthday and all drinks were free! What a great start to the day.

Casa Loma Castle: We hopped in our car and drove over here. Anddddd found out tickets are a little bit pricey + you have to pay for parking (there are streets with free parking nearby). We opted out of the tour tickets and just walked around outside. They had cute holiday decorations up so it was still nice. They do have shows and other events at night, which may be more bang for your buck.

Bata Shoe Museum: This place was super cute and definitely worth a stop! The rooms get a little bit repetitive, but overall I would definitely stop in.

Hogtown Vegan: We went here for lunch and it was delish! There are two locations to choose from. The food was really good and the atmosphere was cuteeee.

We dropped off our car and headed out for shopping and more in Kensington Market. It’s a super cute area – definitely more hipster with street art, vintage, shops, record stores and breweries. We went to way more than this, but some of my faves places were:
-The Cocktail Emporium – SO CUTE. Great prices and unique stuff for making drinks. I tried to find some of the stuff on Amazon when I got home and couldn’t.
-Space Vintage
-Kensington Brewery
-Blue Banana Market
-Sonic Boom Record Store (a little bit further down)

We went to Gusto 101 for dinner – really good pasta and pizza. I would recommend making a reservation. Then got drinks at Bovine Sex Club – a divey bar with live music.


I realllyyyyyyyy wanted to go to The Crazy Doll House in Leslieville so I built our morning around this. So first stop – the house! It’s weird and cool and very Atlas Obscura.

Then we walked over and did some shopping at the Tiny Record Shop, Arts Market and Good Neighbour. All super cute and worthwhile stops. We got some avocado toast at Nutbar while we were at it.

Allan Gardens Conservatory: We drove over here next for some free plants! You can walk around the whole thing for free and it’s warm.

After a fairly atypical morning, we jumped back on the tourist wagon and went over to the Distillery District. It was all dressed up for Christmas. There are a ton of shops, restaurants and places to get drinks here.

Back near our airbnb, we got dinner at Pizza Libretto, which was SO GOOD. And ice cream at Cauldron Ice Cream.


We started off our day at the Art Gallery of Ontario. Definitely a must-visit, especially if you need indoor activities. We stopped at the Half House – another Atlas Obscura find – a house that looks like it’s cut in half!

Next up, we had lunch at Maker Pizza (the Downtown location). We love Matty Matheson so we had to give it a try and it didn’t disappoint! It’s mostly a takeout place, but they do have tables if you want to get a box and sit down.

In the afternoon, we headed over to the Ossington area. We got drinks at Bellwood’s Brewery and walked around taking in all the shops and cute streets. We stopped at Grasshopper Records and then got dinner at Hello123. Hello123 was very good. A little bit pretentious, but the food was fresh and all vegan! They had cute drinks that were on special. We then got some more ice cream at Bang Bang Ice Cream.

Toronto in the winter is definitely cold, but also definitely very COOL 😉


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