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, 2026
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: September 25th & 26th, 2026
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: 50 Alexander’s Crossing, Ajax
When: October 3rd – October 31st, 2026
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 26th – October 31st, 2026
Halloween Nights of Lights & Pumpkinville
Taking place at Scarborough Town Centre from September 25th to November 1st, 2026, 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 25th – November 1st 2026
Pick the Perfect Pumpkin at Reesor’s Farm
Save this one for later in September.
Reesor’s Farm Market in Markham opens its pick-your-own pumpkin patch and corn maze on September 18, giving you seven acres of fall fun to explore together.
Wander through the corn maze, find the pumpkin destined for your front porch and stop at the farm market afterward for baked goods and other seasonal treats. Turn the date into a two-parter by taking your pumpkins home for a carving competition.
Where: 10825 Ninth Line, Markham
When: September 18th – November 1st, 2026
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 14th – 18th, 2026
Walk Through High Park When the Leaves Change
Sometimes the simplest dates are the best ones.
Once Toronto’s leaves start turning, grab coffees and head to High Park for a walk through the fall colours. With hundreds of acres of green space, trails and plenty of places to wander, you can easily spend a few hours here without needing much of a plan.
Make it even better by heading into Roncesvalles afterward for food or drinks.
Where: 1873 Bloor St W, High Park
Have a Spooky Dinner at Storm Crow Manor
For a spooky date night that you can do year-round, head to Storm Crow Manor at 580 Church Street. The sci-fi, horror and geek-themed restaurant feels made for Halloween lovers, with themed rooms and menu items like Dungeon Poutine and the Fire Walk Margarita.
It’s an easy pick if you want the creepy atmosphere without waiting for October, or if your ideal date night involves dinner with a side of the unexpected.
Where: 580 Church Street
When: Monday from 4–11 p.m.; Tuesday–Thursday and Sunday from 12–11 p.m.; Friday–Saturday from 12 p.m.–12 a.m
Spooky & Scary Date Ideas
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: October 3rd – October 31st, 2026
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 25nd – November 1, 2026
ROM After Dark
When: October 30 & 31, 2026
Spend Halloween after dark at the ROM with two nights of its 19+ ROM After Dark series. This year, you can celebrate All Hallow’s Eve on October 30 or keep the Halloween festivities going with Trick or Treat on October 31.
Explore the museum after hours while enjoying music, performances, food and drinks throughout the night. It’s the perfect Halloween date if you want to dress up, grab a drink and experience the museum in a completely different way.
Located: Royal Ontario Museum, 100 Queens Park, Toronto
When: All Hallow’s Eve on October 30, and Trick or Treat on October 31, 2026
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 26th – October 31st, 2026
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 5th – November 1st, 2026
Get Lost in a Corn Maze at Downey’s Farm
Nothing says fall date quite like getting completely lost in a corn maze together. Downey’s Farm is bringing back its fall festivities with an eight-acre corn maze, wagon rides, farm animals, the Boo Barn, duck races, jumping pillows, pedal carts and plenty more to explore.
If you’re visiting on the weekend, you’ll also get access to live entertainment, puppet shows and other activities that aren’t available during the week.
Grab your favourite person, throw on your best fall outfit and make an afternoon of it, just maybe don’t let the person with no sense of direction lead the way through the maze.
When: September 19 – October 31, 2026
Knox Pumpkin Farm
Lean into fall with a trip to Knox Pumpkin Farm, where you can spend the day soaking up all the classic farm fun and picking out the perfect pumpkin together.
Make an afternoon of exploring the farm, snapping some cute fall photos and hopping on a wagon ride which runs at 12, 2 and 4 p.m. on weekdays.
It’s an easy excuse to get out of the city, throw on your favourite fall outfit and fully embrace pumpkin season.
Located: 6325 Enfield Rd, Hampton, ON
When: September 26 – October 31, 2026 | 10 a.m. – 5 p.m.
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 10am-5:30pm (Open until 11pm Fridays and Saturdays)
Brooks Farms
Make the most of apple season with a fall date at Brooks Farms, where you can head into the orchard and pick your own apples together.
Once you’ve filled your bag, keep the date going with a stop at the Farm Market Bakery & Cafe or grab a bite and a cold brew at The Shady Sheep: Bites & Brews. There’s also the Barnyard Playland and seasonal farm events if you want to spend a little longer exploring.
During September and October, the farm is open from 9 a.m. to 4 p.m., with last admission at 3 p.m.
Come for the apples, stay for the baked goods, arguably the best part of any fall farm date.
Located: 122 Ashworth Road, Mount Albert
When: September 12th through October 2026
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 20th – October 31st, 2026
Applewood Farm & Winery
Trade the usual winery date for something a little more fall-inspired at Applewood Farm & Winery, where you can sip fruit wines, cider and mead made with fruit and honey harvested right on the farm.
There are also a couple of special dates worth adding to your calendar. On September 12 from 11 a.m. to 4 p.m., the farm is hosting its Fall Market & Mingle with local vendors, food, live music and drinks on the patio. Or make it a cozy evening date on September 18, when Applewood stays open until 9 p.m. for Campfire Night.
Starting September 25, the fall fun really kicks off with the opening of the farm’s giant corn maze and pumpkin patch, running on weekends throughout October. So you can sip something local, get lost in the maze and pick out a pumpkin all in one date.
Regular Winery & Patio Hours: Friday from 12–5 p.m. and Saturday–Sunday from 11 a.m.–5 p.m. The farm is closed Monday through Thursday.
Wine, pumpkins and a corn maze? Consider your fall date planned.
Located: 2055 Saintfield Road, Seagrave ON
When: Open Fridays from 12–5 p.m. and Saturdays and Sundays from 11 a.m.–5 p.m.; fall activities begin September 25 and run on weekends throughout October.
Looking for a date idea that’s a little less spooky? Check out Toronto’s Best First Date Spots That Aren’t Awkward for more places to keep in mind for your next night out.
