Your Ultimate Guide to Toronto Fall Date Ideas

Festivals, spooky dates, and the perfect ideas for colder weather are here!

At datenight, we always welcome October with open arms! Seasonal drinks and treats, date ideas galore whether you love everything spooky or everything cozy, and so many fun things to do before the weather turns and a long winter arrives. You can find fall dates at virtually every corner you turn in Toronto and the GTA this season, so we’re bringing you the ultimate list of events, festivals, fairs, and farms to check out with your date this October!

See below for the ultimate fall date ideas round-up:

Festivals, Events & Fairs

Nightmarket TO Harvest Festival

Our favourite time of the year is here and we’re thrilled that Nightmarket TO is bringing back their annual Harvest Festival to Mississauga! NMTO will be hosting a 10-day harvest festival at Square One Shopping Centre with rides, games and a harvest marketplace.

Located: Square One Shopping Centre Lot P3, Mississauga

When: September 29th – October 8th, 2023

Toronto Oktoberfest

Toronto’s favourite fall festival, Toronto Oktoberfest, is back! Just because summer’s done doesn’t mean the party stops, and we can’t wait for this epic Bavarian-style fall festival full of music, food, and of course beer!

You and your date can look forward to non-stop fun among Bavarian communal tables and benches direct from Germany lining the Festhalle, an outdoor Bavarian Village, and an atmosphere so authentic you’ll feel like you’ve been transported to Munich.

Located: Garrison Common at Fort York

When: October 6th & 7th, 2023

Spooktacular Light Show

Experience the largest family friendly Halloween Light Show like none other! Spooktacular Light Show will be featuring over 2 million lights on a 2km route of your family fun favourite characters, pumpkin filled drive thru tunnel, from 2D to 3D displays, music lights and much more this Halloween season!

Located: 1389 Brock Rd, Pickering, North of Hwy 407 and 10232 Fourth Line Nassagaweya, Milton

When: September 29th – October 31st, 2023

Pumpkins After Dark

Pumpkins After Dark is Canada’s award-winning outdoor Halloween event. Featuring over 6,000+ hand-carved pumpkins, this one-of-a-kind walk-through experience is the must-see event of the fall season. Grab some car snacks and drive your way through a 2.5km tunnel and trail of light installations. The whole event will take you around 45 minutes to one hour, perfect for heading out to dinner in the area afterwards!

Located: Country Heritage Park at 8560 Tremaine Road, Milton

When: September 23rd – October 31st, 2023

Halloween Nights of Lights & Pumpkinville

Taking place at Scarborough Town Centre from September 30th to October 31st, 2023, Halloween Nights of Lights will now be a thrilling, immersive walk-through experience for the 2023 season.

Bigger and better, this year’s experience will feature more than 2 million LED and RGB lights animated and synchronized to your favourite Halloween tunes. Continue the fun inside Pumpkinville, a fun fair located at the end of the Nights of Lights trail featuring larger-than-life pumpkin sculptures and village featuring over 25,000 real pumpkins.

Located: Scarborough Town Centre, 500 Progress Ave

When: September 30th – October 31st

The Burton Bar

If you’re a huge Tim Burton fan then you’re going to want to explore this Halloween popup in Toronto at The Burton Bar. Coming soon in October is this Tim Burton inspired, immersive Halloween bar with haunting decor, themed drinks and spooky quests! You’ll want to also try out their secret, dark cocktails. Each ticket comes with: 

  • 1 x Boozy Welcome Drink (non alc versions available)
  • 90 minutes in our themed Halloween bar
  • Games, additional activations and a Ghost Host

Located: MADO, 144 Yonge St., Toronto

When: October 4th – 31st, 2023

Toronto After Dark Film Festival

Save the dates as the Toronto After Dark Film Festival is back! This festival is one of the world’s leading showcases of New Horror, Sci-Fi and Action Movies with thousands of people including film lovers, press, industry and filmmakers who attend. This year, expect 2 prime time evening screenings and a matinee screening on each of the weekend days as well as 2 pre-screening social events on site at the theatre.

Located: Scotiabank Theatre, 259 Richmond St West, Toronto

When: October 18th – 22nd, 2023

Howl’oween at the Bentway

Halloween is set to be a memorable day for our furry friends! Howl’oween is returning to The Bentway and will be taking place on Saturday, October 28th, from 12pm to 4:00pm. The Bentway warmly welcomes all local canines and their companions to partake in a whimsical dog costume parade. This event will include fantastic prizes, musical entertainment, a fun photo selfie corner, cozy beverages, and local pet-friendly vendors. Get ready for an unforgettable canine costume celebration!

When: Saturday, October 28th, from 12pm to 4:00pm

Location: The Bentway, 250 Fort York Blvd

Try This New Drink at Chotto Matte

Introducing Chotto Matte‘s latest seasonal cocktail, the El Ramo Immortal, this drink draws inspiration from Peruvian Day of the Dead traditions. Available for one week only, This exclusive cocktail incorporates seasonal ingredients that will have you wanting more!

The El Ramo Immortal is a well-aged rum concoction featuring dry Vermouth, banana cordial, elderflower, lime, and Peychaud bitters. Indulge in an evening at Chotto Matte to celebrate the Day of the Dead and savour the diverse flavours of Nikkei cuisine paired with this fruity-bitter drink crafted exclusively for this year’s festivities!

When: One week only starting October 30 until November 5

Location: 161 Bay St., Toronto

Spooky & Scary Date Ideas

Haunting of Hexwood

Get ready this spooky season for Canada’s largest haunted town experience! Haunting at Hexwood is a 23 acre modern day small town sitting on a 90 acre plot of land. This space is located in Pickering, ON and was specifically built for feature films, tv series & commercials. Expect to see 6 main attraction haunts, 13 store fronts and activations including:

  • Full functioning tattoo parlour with shop FYink
  • A haunted photo gallery partnership with photographer Briony
  • Give away station with large Toronto based brand of Ghost drops official
  • A haunted coffee shop with deadly grounds, a shop specializing in gore
  • A psychic, tarot reader, crystal shop 
  • A Halloween themed candy shop and so much more!

Located: WFW Backlot Film Studio, 3800 Sideline 32, Pickering, ON

When: October 6th – 31st, 2023

The Isabella Street Seance

If the other horror attractions are baby food for you and your date, this experience is SURE to scare the socks off you. This is truly a once in a lifetime experience (because you may be too scared to go back)!

Jaymes White is a celebrity mentalist, mindreader (and possibly witch), inviting groups of brave souls to a chilling recreation of an authentic Victorian Séance at one of Toronto’s oldest and most haunted Inns.

To be warned: this soul-shaking psychological experience is not intended for the weak or faint of heart.

Located: Meet in front of 640 Church Street (beside A&W). You will then be escorted a short walking distance to the Séance Location.

When: September 29th – November 25th, 2023

Casa Loma Legends of Horror

Usually, Casa Loma is a romantic castle to stroll through, or enjoy garden and terrace dinner dates at. In October, it’s a terrifying immersive horror experience. Brave the castle with your date while walking through a 2 km trail of the castle’s gardens, tunnels and some of the “darkest spaces never open to the public.” As if that’s not scary enough, they’re bringing the castle walls to life, literally, with 3D projections, theatrics, and live actors.

Located: 1 Austin Terrace, Toronto

When: September 29th – October 31st, 2023

Halloween Haunt

What’s spooky season without this staple haunt happening at Canada’s Wonderland? If a wonderland full of opportunities to get scared sounds like your fall cup of tea, you have to make a point of heading here.

The dark tunnels under the mountain are no place for humans, especially after dark. When the creatures of the pit awaken, they use their mind-warping tricks and luminescent traps to confuse their prey, luring them to a ghastly demise. The vibrant lights may appear to promise salvation, but they’re only a harbinger of the pandemonium that is about to ensue, as you’re embraced by the cold, dark death of the shadows and the creatures that live within.

Located: 1 Canada’s Wonderland Drive, Vaughan

When: Select nights, September 22nd – October 29th, 2023

ROM After Dark

This 19+ monthly themed series has officially returned with several events including “Trick or Treat” on October 27th, 2023 where you can party it up after hours while exploring Canada’s most visited museum. Expect curated music, visual arts, pop-up performances, and food & drink for an entry price of $40. Each ticket comes with a drink!

Located: Royal Ontario Museum, 100 Queens Park, Toronto

When: Once a month from September – December, 2023; 7:30 PM – 11:30 PM (last entry: 10:30 PM)

The Black Lagoon Pop-Up

Black Lagoon is an immersive, creepy-as-hell experience that pays homage to the macabre and throws in a splash of goth and metal for good measure. Wear your costume to these dark dungeons of drink and enjoy innovative and deliciously spooky cocktails!

Located: Bar Mordecai, 1272 Dundas Street West, Toronto

When: October 17th – October 31st, 2023

Snyder’s Fear Farm Haunted House

If you haven’t gotten your fix of fear in the city, venture out east and visit Fear Farm in Bright, Ontario this season. The farm has six different haunted attractions you can explore including a hay ride through the haunted grounds, a pitch-black corn maze, a multi-level haunted house, and a carnival.

If you need a bit of a snack after all that screaming then make sure to head over to one of the many food vendors on the farm that will be serving up some of your favourite fall treats including butter tarts and a warm glass of apple cider.

Located: 936685 Blenheim Rd, Bright ON

When: September 30th – October 29th, 2023

Fall Farm Date Ideas

Pingles Harvest Festival at the Farm

Celebrate fall on the farm with apple and pumpkin picking, wagon rides for the kids, a giant 6.5-acre corn maze, the Playland, a fall-inspired menu, an on-farm bar, multiple coffee shacks and more! Pingles Farm has been known to up their Harvest Festival game each year with delicious and inventive food and drink items, take-home food for your fall feasts, installations and activities, and market items to purchase!

Located: 1805 Taunton Road East, Hampton

When: September 8th – October 29th, 2023

During the week (Tuesday – Thursday) enjoy a more peaceful experience, for a discounted rate!  
*No food, live music, bar, or food access Tues – Thurs.

Pumpkin Fest at Downey’s Farm

Of course these guys made the list. Downey’s Farm has been the site of some iconic fall photography around the GTA with their iconic pumpkin patch and farm-front. Did you know that behind all of that, is an insanely fun Pumpkinfest happening right through the gates? Enjoy lots of fun activities at their play area including wagon rides, live entertainment, farm animals, and an 8-Acre Corn Maze. Check out this map for a full list of  EVERYTHING you can do!

Located: 13682 Heart Lake Rd, Caledon

When: September 23rd – October 31st, 2023; Daily 9am-5pm

Knox Pumpkin Farm

Visit Knox Pumpkin Farm away from the busy city life this fall season and immerse yourselves with nature. Just a short drive east from Toronto to Hampton, ON, you can sample delicious homemade goods and frolic through the pumpkin fields.

Located: 6325 Enfield Rd, Hampton, ON

When: September 23 – October 31st, 2023; 5pm-10pm

Chudleigh’s Entertainment Farm

If you haven’t been to his Milton farm famous for their delicious Apple Blossom desserts, you need to put it on your list. Walking through the entrance brings you to a whole new fall farm world with a huge patio and live music area, a Cidery to taste flights of their own hard apple cider (and some fun cocktails), rows and rows of apples and pumpkins, farm animals, photo opps, and a market to bring a little but of Chudleigh’s home with you.

Located: 9528 Regional Road 25, Halton Hills

When: Open daily 8:30am-6pm (Open until 11pm Fridays and Saturdays)

Brooks Farms

While you may think it’s just a regular pumpkin patch farm, Brooks Farms also invites you inside to their 2nd annual “After Dark Spooky Festival” for thrills and chills. This transported Halloweentown includes lots of excitement, attractions, and activities for those who want to be frightened.

Located: 122 Ashworth Road, Mount Albert 

When: Friday and Saturday evenings in October

Muskoka Lakes Winery & Farm

Johnston’s Cranberries at Muskoka Lakes Farm & Winery have started up their Harvest activities again. Visit this marsh and wade through 400,000 pounds of cranberries with your friends or date for a truly unique experience.

Spend the day at Muskoka Lakes Winery & Farm and go on a wagon tour, have a guided wine tasting, shop for fresh cranberries, and explore the hiking trails with beautiful scenery, too. Open seven days a week!

Located: 1074 Cranberry Rd, Bala

When: September 23th – October 31st, 2023

Applewood Farm & Winery

This family-run farm and winery has all the fall aesthetic you need and love for the season. Pick your own pumpkins, get lost is a corn maze, and check out the cute installations and animal enclosures at this spot northeast of the city.

October 5th is the Thanksgiving centerpiece workshop from 6-8pm led by @perennialpetals 

Located: 2055 Saintfield Road, Seagrave ON

When: September 16th – October 31st, 2023 ; Open Thurs-Fri 11am-4pm, Sat-Sun 10am-4pm

We’re sharing more date ideas throughout this season from all things haunted, to all things pumpkin spice, and more. Stay tuned and keep your eyes peeled here for the best Toronto and GTA date ideas!

Subscribe to receive our weekly newsletter

Your destination for date ideas and experiences across Canada

Articles, Giveaways, Gift Ideas & More