Halloween Food, Drink, and Parties Near Oakwood Village 2026

Spooky Halloween cruise with costume contest and DJ.

Illustration of a Halloween party at dusk with costumed characters around a punch bowl, a ghost, pumpkins and string lights (Halloween on Church Street Block Party)

Halloween on Church Street Block Party

Toronto

Canada's largest Halloween street party taking over Church Street.

Illustration of a glowing Halloween party scene with a pumpkin, a witch figure, a cat and a cake on a purple dance floor (Ghostly Greetings from the Haunted Mill Halloween Party)

Ghostly Greetings from the Haunted Mill Halloween Party

Toronto

Spooky dinner and dance party featuring live music by Groove Marmalade.

Illustration of a vampire and a witch figure on a glowing dance floor with a large pumpkin and jack-o'-lanterns (Haunted Halloween Boat Party Cruise - Toronto)

Haunted Halloween Boat Party Cruise - Toronto

Toronto 6 mi $$$

Three-deck floating nightclub cruise featuring live music and skyline views.

Illustration of small costumed figures toasting with a frothy mug beside wooden barrels, pumpkins and autumn trees outdoors (Halloween Boat Party Cruise Toronto 2026)

Halloween Boat Party Cruise Toronto 2026

Toronto 6 mi

Costume boat party with a heated salon and open-air rooftop deck.

Illustration of a Halloween nightclub where costumed clay partygoers dance beneath purple and green lights near a stage (House of Horrors Halloween Costume Party)

House of Horrors Halloween Costume Party

Costume bash at Oria Nightclub with DJs and late bar service.

Illustration of costumed figures beside a table with two gold trophies on a hay covered stage with pumpkins and string lights (Nineties By Nature Halloween Party 2026)

Nineties By Nature Halloween Party 2026

Oct 30 – Oct 31

Costume dance party featuring nineties hip hop, R&B, and club anthems.

Oktoberfresh Fest 2026

Sat, Sep 19

Etobicoke 6 mi $$

Craft beers, German food specials, festival games, and live music.

Illustration of costumed figures near striped booths and pumpkin displays on a grassy town square with orange autumn trees (Toronto Fall Outdoor Market Festival & Food Festival)

Toronto Fall Outdoor Market Festival & Food Festival

Sep 18 – Sep 20

Toronto 7 mi Free

Outdoor market with local artisans, handmade goods, and food vendors.

Illustration of costumed characters dancing on a glowing purple dance floor surrounded by jack-o'-lanterns and lanterns (Don't F**K With The Old School Halloween)

Don't F**K With The Old School Halloween

Downtown party featuring classic hip-hop and house music.

Toronto Fall Pop-Up Market & Artisan Festival

Sep 25 – Sep 27

Toronto Free

Showcases handcrafted goods, jewelry, home décor, and gourmet baked goods.

Illustration of a Halloween costume contest on an outdoor stage with costumed figures, a ghost, a trophy and a watching crowd (Psycho Halloween Costume Day Party)

Psycho Halloween Costume Day Party

Daytime Halloween costume party featuring Hip Hop, RnB, and Afrobeats

Illustration of clay characters in Halloween costumes on a stage with a golden trophy, a ghost and an audience (Bodacious Curves Body Positive Halloween Party)

Bodacious Curves Body Positive Halloween Party

Oct 24 – Oct 25

Inclusive costume celebration featuring music from DJ AK Blaze and door prizes.

Fall In

Sep 25 – Sep 26

Toronto 8 mi $

Toronto dance party featuring Afrobeats, Amapiano, and Dancehall music.

Illustration of a Halloween costume contest on a decorated barn stage with ghosts, a trophy table and pumpkins in front (Ladies Only Halloween Costume Party)

Ladies Only Halloween Costume Party

Toronto $$$

Ladies-only costume dance party featuring DJ sets and an open bar.

Illustration of a glowing Halloween party where a vampire and a girl stand by a pumpkin disco ball near a cake and a cat (Disney Halloween Mashup Drag Bingo Brunch)

Disney Halloween Mashup Drag Bingo Brunch

Sun, Oct 25

Disney Halloween-themed drag performances and bingo rounds with prizes.

Fright and Fetish

Halloween party featuring magicians, burlesque performances, live music, and cash prizes.

Illustration of smiling ghost figures and a small costumed child beside pumpkins and paint cups on a wooden table (Trick or Treat: A Halloween Chocolate-Making Workshop)

Trick or Treat: A Halloween Chocolate-Making Workshop

Toronto $$$

Hands-on Belgian chocolate bar crafting with spooky toppings and painted moulds.

Illustration of a Halloween nightclub where costumed clay partygoers dance beneath purple and green lights near a stage (Obsession The Halloween Costume Bash)

Obsession The Halloween Costume Bash

Oct 30 – Oct 31

Downtown costume party with prizes, multi-genre music, and bottle service.

Run The Track 2.0 Halloween Party

Sat, Oct 24

Vaughan 10 mi $

Live music showcases, DJ sets, and a haunted house experience.

Halloween Masquerade Party

Scarborough 11 mi $$

House music costume party with live DJs and a midnight snack bar.

Illustration of a Halloween costume contest on an outdoor stage with costumed figures, a ghost, a trophy and a watching crowd (After Dark Halloween Bash)

After Dark Halloween Bash

Vaughan 12 mi $

Costume contest with prizes, an appetizer, and a complimentary drink.

Illustration of a Halloween costume contest on a small stage with a pumpkin, robot, witch, ghosts, trophy and audience (Halloween Pumpkin Carving, Painting, and Sip Night)

Halloween Pumpkin Carving, Painting, and Sip Night

Toronto 7 mi $$$

Features pumpkin crafting, studio drinks and snacks, and a costume contest.

Illustration of a candlelit Halloween dinner table with small pumpkins, a friendly ghost and two witch costumed figures (Fresh Spooky Pasta Workshop)

Fresh Spooky Pasta Workshop

Vaughan 10 mi $$$

Handcraft haunted orecchiette, bat-wing farfalle, and mummy fettuccine at individual work-stations.

Halloween Drag Bingo

Toronto

Drag performances, four bingo rounds, and prizes co-hosted by Toronto queens.

Illustration of a Halloween gathering at dusk with a smiling ghost, costumed figures, glowing jack-o'-lanterns and lights (Oktoberfest at The Distillery District, poured by Mill Street Brewery)

Oktoberfest at The Distillery District, poured by Mill Street Brewery

Sep 19 – Oct 4

Toronto 5 mi

Bavarian food, Mill Street beer, live polka, and courtyard games.

Illustration of costumed clay characters toasting with frothy mugs near barrels and pumpkins at an autumn beer festival (Oktoberfest Bierhalle at Liberty Village)

Oktoberfest Bierhalle at Liberty Village

Sep 19 – Sep 20

Features fresh beer releases, live music, and steinholding competitions.

Illustration of a Halloween costume contest on an outdoor stage with costumed figures, a ghost, a trophy and a watching crowd (Rock The Boat: Toronto's Ultimate Halloween Yacht Party 2025)

Rock The Boat: Toronto's Ultimate Halloween Yacht Party 2025

Ultimate Halloween yacht party with skyline views

Illustration of a rooftop Halloween bar at dusk with cocktails, a vampire bartender, pumpkin lanterns and a city skyline (Ripley's Aquarium of Canada: Dark Waters Halloween Event)

Ripley's Aquarium of Canada: Dark Waters Halloween Event

Toronto $$$

Aquarium after dark with tarot readers and costume contest.

Toronto Halloween Fright Fest at NEST