October 23-29 (Toronto)

BOO! We’re heading into the spookiest weekend of the year, and there are so many free Halloween events happening I can’t wait to share with you. While you’re managing costume changes, sugar highs, and pumpkin-carving chaos, I’ve got your weekend plans covered. 👻

My Top Picks This Week Around Toronto

1. 🎃 Riverside Halloween Fest (haunted house & dog costume party) – EAST END

2. 🍫 Inaugural Bloor Street West Candy Crawl! – WEST END

3. 🍬 In-Mall Trick or Treat at Woodbine Mall with costume contest – ETOBICOKE

4. 👕 The Great Kids Stuff Sale for gently used children's items – MIDTOWN

5. 🎨 Halloween Haunt UP street party with costume contests – UPTOWN

🎃 Fall into Greektown | EAST END
Friday-Sunday, October 24-26 (Family activities: Sat 2-5pm, Sun 3-6pm)
Location: The Danforth | Cost: FREE to attend | Age: All ages
🔗 Event Details
From family fun to GreekTown's very first pub crawl, you won't want to miss this. Support businesses in the area and you can win $1000!

📚 Queen Books: A Very Spooky Party | EAST END
Saturday, October 25, 4:00 PM - 8:00 PM
Location: Queen Books | Cost: $6.66/ticket | Age: All ages
🔗 Event Details
Story time, face painting, crafts, and a costume parade! From 6-8pm, an appropriately themed movie (TBA) for slightly bigger kids. Bring your own pillow, blankets, and snuggly things—popcorn provided!

🍎 Friends of Regent Park October Funfest | EAST END
Saturday, October 25, 1:00 PM - 3:00 PM
Location: Regent Park | Cost: FREE | Age: All ages
🔗 Event Details
Join for an afternoon of pumpkin carving, music, dancing, activities, and apple crisp.

🐶 Riverside Halloween Fest & Dog Costume Party | EAST END
Sunday, October 26, 11:00 AM - 3:00 PM
Location: Joel Weeks Park | Cost: FREE admission | Age: All ages
🔗 Event Details
Free kids activities including pumpkin decorating, treats, haunted house, DJ tunes, face painting, vendors, and more! Also free fun for your dogs, including a dog costume contest with judging and prizes, treats, free photobooth!

🎃 Pumpkin Carving and Pancakes | EAST END
Sunday, October 26, 10:00 AM
Location: East York | Cost: FREE | Age: Families with kids 12 and under
🔗 Event Details
Pumpkins from Prince Edward County and all the tools to make a jack-o-lantern. Apple & Cinnamon Pancakes for everyone. One pumpkin per family with all the pancakes you can eat. Registration required.

🎃 Kingsway Pumpkinfest | ETOBICOKE
Saturday, October 25, 10:00 AM - 2:00 PM
Location: The Kingsway | Cost: FREE | Age: All ages
🔗 Event Details
Annual Halloween celebration featuring pumpkin decorating, street market, balloon art, and costume prizes. Trick-or-treating at participating neighborhood stores included.

🎨 Fall MRKT | ETOBICOKE
Saturday, October 25, 11:00 AM - 4:00 PM
Location: Michael Power Park | Cost: FREE admission | Age: All ages
🔗 Event Details
Shop local vendors, enjoy free face painting, and snap a photo in the pumpkin patch.

🎃 Halloween Costume Contest & In-Mall Trick or Treat | ETOBICOKE
Saturday, October 25, 11:00 AM - 5:00 PM
Location: Woodbine Mall | Cost: FREE | Age: All ages
🔗 Event Details
Kids (and parents!) are invited to wear costumes and snap festive photos. Prizes for the top 3 costumes. Pick up your free trick-or-treat bag at Fantasy Fair Customer Service

🕯️ Montgomery's Inn Lantern Tours | ETOBICOKE
Saturday-Sunday, October 25-26, 6:00 PM - 8:00 PM or 8:00 PM - 10:00 PM
Location: Montgomery's Inn | Cost: $15/person | Age: Ages 12+
🔗 Event Details
Uncover eerie tales about past inhabitants of the Inn and Old Town of Islington. Explore the historic house and Islington burying grounds, learn about Victorian death practices.

🎃 Trinity Bellwoods Littles Monster Mash Halloween Party | DOWNTOWN
Sunday, October 26, 10:30 AM - 2:30 PM
Location: Blue Moon Brewery @ STACKT market
Cost: $12-$15/ticket Age: Families with children 6 and under
🔗 Event Details
This not so spooky celebration is packed with fun for kids 6-ish & under. Each ticket includes tasty snacks, monster themed photo area, sensory play stations, arts & crafts fun!

🦖 National Geographic Dig Event at Staples (REGISTRATION ONLY) | DOWNTOWN
Registration open now until sold out (Event: November 5)
Location: Staples Corktown | Cost: FREE | Age: Ages 6+ |🔗 Event Details

👕 The Great Kids Stuff Sale | MIDTOWN
Saturday, October 25, 9:00 AM - 12:00 PM
Location: Eglinton St. George's United Church | FREE to attend | Age: All ages
🔗 Event Details
Gently used, high quality items for children sized Newborn to Youth Medium. Recommend getting there early for best selection. October sale features Fall and Winter items. Now accepting credit cards (and cash or debit).

🎃 Granite Brewery Halloween Mom Meet Up | MIDTOWN
Thursday, October 23 | 1:30 PM
Location: Granite Brewery | Cost: FREE | Age: Moms & babies
🔗 Event Details
Calling all mamas and babies! Join for a relaxed mom meet up. Since it's that time of year, we're embracing Halloween—costumes optional for your little ones! RSVP!

🦖 National Geographic Dig Event at Staples (REGISTRATION ONLY) | MIDTOWN
Registration open now until sold out (Event: November 5)
Location: Staples Midtown | Cost: FREE | Age: Ages 6+ | 🔗 Event Details

👻 Yorkgate Mall Halloween Fun | NORTH YORK
Saturday, October 25, 1:00 PM - 4:00 PM
Location: Yorkgate Mall | Cost: FREE | Age: All ages
🔗 Event Details
The biggest, scariest, and spookiest Halloween celebration EVER! First 250 kids in costume receive a FREE loot treat box and Halloween bucket. FREE pumpkin for each family! Explore the spooky, creepy crawler exhibit. FREE Halloween book for kids.

🎃 Asian Halloween Market | SCARBOROUGH
Sunday, October 26 | 12:00 PM–6:00 PM
Location: Maeli Market | Cost: FREE | Age: All ages
🔗 Event Details
8 curated vendors, FREE Halloween gift packs for the first 100 kids, free face painting from 2pm to 4pm, scary costume contest, bubble blower, cupcake decorating!

🎃 Fairbank Village Pumpkin Giveaway | UPTOWN
Friday, October 24, 4:00 PM - 6:00 PM
Location: Hartley Ave & Eglinton W |Cost: FREE | Age: All ages
🔗 Event Details
Pumpkins, candy, and spooky fun await! FREE pumpkins at 5pm, trick-or-treat scavenger hunt, hotdogs, activities, and sweet prizes. Bring your family for a night full of fall fun!

🍬 Halloween Haunt UP | UPTOWN
Saturday, October 25, 11:00 AM - 5:00 PM
Location: Yonge St (between Roehampton Ave & Glengrove Ave)
Cost: FREE | Age: All ages
🔗Event Details
Annual street party featuring sidewalk sales, buskers, live music, costume contests for kids and pets, and face painting. Traffic closures expected on Yonge Street section. Heavily attended event.

🤸 SmartieGym Halloween Market | UPTOWN
Saturday, October 25, various time slots
Location: Smartiepants St Clair | Cost: FREE to attend | Age: All ages
🔗 Event Details
Children enjoy a FREE hour of play in SmartieGym while parents browse female-founded local vendors offering treats, crafts, and unique finds. Spots are limited!

🦖 National Geographic Dig Event at Staples (REGISTRATION ONLY) | UPTOWN
Registration open now until sold out (Event: November 5)
Location: Staples Leaside | Cost: FREE | Age: Ages 6+ | 🔗 Event Details

🎃 Junction Farmers Market Halloween Fest | WEST END
Saturday, October 25, 9:00 AM - 1:00 PM
Location: Baird Park |Cost: FREE | Age: All ages
🔗 Event Details
Come meet Halloween Panda and snag a special treat! Free face painting, free paint-your-own pumpkin station, kids costume raffle, dog costume contest, free spooktacular photo booth with props, and so much more!

🦇 Bats, Rats, and Moths, Oh My! High Park Walk | WEST END
Saturday, October 25, 10:00 AM - 11:30 AM
Location: High Park Nature Centre | Cost: $10/person | Age: Recommended ages 4+
🔗 Event Details
Who comes out after we go to bed? Can you hear the bats flying overhead, or the haunting who? who? of the owls? Join for a not so spooky nature walk to discover High Park after dark!

🎃 Pumpkin Fest | WEST END
Saturday, October 25 | 4:00 PM–8:00 PM
Location: Dupont & Christie | Cost: FREE | Age: All ages 🔗 Event Details 
Free pumpkins and painting party, live Day of the Dead band, trick-or-treating, giant skeletons, ghost photo booths, DJ dance party, and street food marketplace!

👻 Bloor West Halloween Fest | WEST END
Saturday, October 25 | 11:00 AM–3:00 PM
Location: Bloor West Village | Cost: FREE | Age: All ages |🔗 Event Details
Spooky Squad! Come celebrate Halloween Fest where little ghouls (and big kids too) can have a frightfully good time! Go on a trick-or-treating trail across the Village!

🍬 Bloor St W Candy Crawl | WEST END
Sunday, October 26 | 12:00 PM–4:00 PM
Location: Bloor St W (Bloordale & Bloorcourt) | Cost: FREE | Age: All ages
🔗 Event Details
The first-ever Bloor St W Candy Crawl at participating Bloordale and Bloorcourt businesses! Costumes are VERY much encouraged. Check the Candy Crawl Map!

🎃 Toronto Sunday Market: Halloween Market | WEST END
Sunday, October 26 | 11:00 AM–4:00 PM
Location: The Parkdale Hall | Cost: FREE to attend | Age: All ages
🔗 Event Details
A day of shopping, delicious treats, and Halloween-themed activities. Come in your best costume and explore all the unique vendors .Trick-or-Treat candy for the kids!

🎃 Sorauren Market Halloween Harvest | WEST END
Monday, October 27 | 3:00 PM–7:00 PM
Location: Sorauren Park | Cost: FREE | Age: All ages
🔗 Event Details
Dress up in your best costume (make sure you dress your dog up too!), paint a pumpkin, make some candy crafts, and get a trick-or-treat basket!