17 Best Costumes from Halloween on Church St.

Hundreds of people celebrated Halloween from 6PM to 2AM last night on the pedestrian-only streets in the Church-Wellesley Village. There were so many creative costumes on this stretch spanning six blocks from Wood St. to Gloucester St. People came to strut their Halloween costumes, take pictures, enjoy the local pubs, watch fire juggling acts, and dance in a lively crowd. This street party is one of the best in the city!

I went to an event the other day dressed as pacman and the ghosts with a group, but the entire group wasn’t here today so I had to be creative.

There were some people who dressed up as really frightening monsters, but there were still many families who came out to enjoy the scene. Some people call it a street party, but besides the one area where a tent is set up for crowds to dance to the music, the rest of the environment is pretty relaxed and enjoyable. I really like that this event is (somewhat) suitable for all ages! This is my second time at Church/Wellesley for Halloween, and I would definitely recommend it for next year if you’re looking for something a little more low-key than a pub/club that captures the essence of innocent Halloween nights from your childhood.

I’m sure you’re dying to see what Halloween costumes are listed as the best!

Here is my list of the top 17 costumes last night.

1. The Toronto Sign
I LOVE THIS! If you can’t get to the Toronto sign at Nathan Phillips Square then don’t you worry because it’ll come to you. What a creative bunch of Torontonians, and they were all so friendly too!


2. Beekeeper, Bees and their Hive
That beehive is fabulous. You know you’re a true Halloween fan when you give up using your hands for the entire night just to show up in this costume. Atleast he won’t be hungry with all that honey in there.


3. Day of the Dead Skulls
Mexican Day of the Dead face paint, skulls and props were everywhere. There were paper mache masks and full-on skulls like this. There were also disco skulls which were pretty cool. It was selfie central all over!


4. Police Fashionista
This dress is outstanding. He used “do not cross” police tape for the entire dress and it was really bouncy and voluminous – this needs to be in Fashion Week! I hope this dress makes an appearance at pride as well when the police are welcome back into the parade. I wonder if there’s a political statement to this costume?


5. Dinosaur Group
I have been seeing dinosaurs everywhere this Halloween but to see five dinosaurs all at once is a treat. So cute!


6. The Left Shark
Having fun with Katy Perry’s left shark from her Superbowl performance years ago.


7. Baby Shark + Fam

Baby shark, doo doo doo doo doo doo
Baby shark, doo doo doo doo doo doo
Baby shark, doo doo doo doo doo doo
Baby shark!

Mommy shark, doo doo doo doo doo doo
Mommy shark, doo doo doo doo doo doo
Mommy shark, doo doo doo doo doo doo
Mommy shark!

Daddy shark, doo doo doo doo doo doo
Daddy shark, doo doo doo doo doo doo
Daddy shark, doo doo doo doo doo doo
Daddy shark!

You’re welcome. This costume is SO 2018!


8. Marilyn Monroe
Marilyn Monroe even has the whole flimsy dress blowing up in the wind thing going on. How beautiful!


9. Handmaid with a Child
This handmaid kept repeating: “HE’S PERFECT”. Should we be worried?


10. Prince Harry and Meghan Markle
I died laughing when I looked up at a bar and saw these two waving to the people below.


11. Weed Man
All smiles in weed land #Canada. This guy was so cool and chill I couldn’t not take a photo with him.


12. Home-made Snow White 
What a youthful spirit! This woman is so cute. She came out with the mission to spread her Disney joy and cheer to everyone. Her costume is home-made by the way! Best snow white I’ve ever seen.


13. Halloween Fashionistas
“This is Halloween, everybody make a scene. Halloween, halloween, halloween, HALLOWEEN!” I think these are the Pumpkin king and queen? Not sure, but they really embody the spirit of Halloween.

14. Lego People
Lego takeover everyone!! By the way… are there any air holes in those things?!


15. Sanrio Rilakkuma Bear
So cute!! I got the warmest, cuddliest bear hug from Rilakkuma. Best. Night. Ever.


16. Jellyfish
Someone call Ripleys! This jellyfish umbrella is so creative and magical. The string lights are a nice touch.


17. Buzz Lightyear
This moment with the child looking at Buzz Lightyear was too precious! I only hope he can breathe in there…

Have you been to Halloween on Church Street? What do you enjoy the most about this event? Have you seen an unforgettable Halloween costume here? Let me know in the comments below!

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