As the capital of Ontario and the nation’s largest city, Toronto might just be the embodiment of what it means to be Canadian. Think of it as an ever-evolving celebration of cultures coming together to create something utterly original. It’s bold and sophisticated, edgy and elegant, while embracing its history and welcoming the future.
There’s so much to discover beyond the city, whether seeing fall leaves en route to Ottawa, driving south to wine country, or traveling to Ontario’s southermost point to witness the autumn migration of monarch butterflies. Before you set off on a three- to five-day adventure, check out Toronto’s arts, culture, and food scenes.
Artful encounters/experiences: September signals the start of film-fest season with the Toronto International Film Festival garnering big names like Canadians Atom Egoyan and Ellen Page. Mid-October brings the Planet in Focus Environmental Film Festival, which is celebrating its 20th season of using film as a catalyst to raise awareness about our planet’s health. From the world’s largest presenter of Indigenous screen content comes the eponymous imagineNATIVE Film & Media Arts Festival, with an original lineup of Indigenous-made media arts and exhibitions.
Art thrives outdoors too. Get acquainted with the city’s vibrant waterfront neighborhoods on foot while checking out the art installations that comprise the Toronto Biennial of Art, which kicks off in September and runs to December. Ponder the curatorial vision of the event — How Are We In Relation? — as you learn histories of the Indigenous people, immigrants, and settlers who shaped the city.
A different artful experience takes place on Toronto’s streets October 5 from sunset to sunrise for one night only. Nuit Blanche (White Night) is a free contemporary art event that invites people to view the city’s paradoxical and evolutional cycle through the lens of this year’s theme: Continuum.
Nature also puts on a show in fall when the leaves change color. It’s easy to revel in the beauty of the season right in the city. Just make your way to High Park or take a 13-minute ride on the ferry from Jack Layton Ferry Terminal to the nearby Toronto Islands, a car-free haven. Walk the pathways and cross bridges that connect the fifteen islands that make up this magical place.
Global eating: One of the best ways to get a taste for Toronto’s diverse cultures is through its cuisine. New resto Fet Zun offers a menu of Middle Eastern snacks like grilled halloumi cheese and smoky baba ghanouj, inspired by bites you’d find in markets. Mini-chain Planta serves 100 per cent plant-based pan-Asian dishes with inventive flourishes. Think spicy “ahi” watermelon sushi, and wonton soup made with shaved truffles.
Delve into the “inherently Canadian” menu at Nique for a cultural mosaic of eats like pork belly steamed buns, avocado toast with cotija cheese, and heritage pork accompanied by maple-bourbon mustard. Everything is made with sustainable and ethically sourced ingredients. And throughout October indulge your sweet tooth with a tasty walking tour during the Toronto Chocolate Festival.
Unique sleeps: All that mind-expanding and belly-stretching requires a good rest. The pet-friendly Bisha Hotel lets you continue your art-filled day with stylish rooms swathed in marble and crushed velvet. Splurge on The Bisha Suite, 2,000 square feet of crush-worthy space designed by rocker Lenny Kravitz. And if an urban resort sounds appealing, the Hotel X Toronto amply delivers with its lakeside location, rooftop pool, cinema, tennis courts, Guerlain spa, tri-level bar, among other amazing amenities. You can even create your own suite, linking your preferred combo of rooms together.
Get beyond the city — go southwest for wine and waterfalls
Hamilton (42 miles/45-minute drive)
Driving southwest from Toronto on Highway 403 takes you to Hamilton, which sits on the western shore of Lake Ontario. Once known as the steel capital of Canada, its burgeoning arts scene has added a new dimension to the city. See for yourself in mid-September at Supercrawl 2019. The free indie arts and music fest will host artists such as Canadian icon Buffy Sainte-Marie and Toronto-born Bahamas, among others.
When wandering downtown, drop by the Art Gallery of Hamilton to see cool exhibits like This is Serious: Canadian Indie Comics. Film fans should be sure to stroll past Hamilton City Hall at 71 Main Street West. The building, among others both in Hamilton and Toronto, was used as a set in the Oscar award-winning film, The Shape of Water. Thanks to its location on the Niagara Escarpment, Hamilton is a waterworld in its own right, with more than 100 cascades you can marvel at during a self-guided tour before resuming your journey.
Niagara-on-the-Lake (46 miles/1-hour drive)
Fall is crush season in Niagara-on-the-Lake, when 20-plus wineries harvest grapes, adding some extra excitement to this bucolic community. The region is composed of a range of microclimates, fertile ground for varietals that span the spectrum from Chardonnay and Cabernet Franc to Riesling and Vidal. Get an up-close look at this fascinating industry during the Niagara Grape and Wine Festival in mid-September, Canada’s largest wine festival offering more than 100 events, including pairings of local cuisine and wines.
Along with its historic downtown, Niagara-on-the-Lake is a center for world-class theater, with the Shaw Festival in full swing during fall. (If you’re not driving, hop the shuttle from downtown Toronto or Burlington.) Take in performances such as Mae West’s Sex, Tennessee Williams’ The Glass Menagerie, and comedy-heist The Lady Killers. A mere 25-minute drive (14 miles) south on Highway 405 is worth the detour to be wowed by Niagara Falls’ monstrous walls of water before making your way back to Toronto.
Extend your stay at the Shaw Club Hotel, conveniently located across the street from the Shaw Theatre. Snuggle in to 320-thread count sheets, read the complimentary morning paper when you awake, and if you want some extra company ask for a pet fish to be brought to your room.
Point Pelee National Park (180 miles/3-hour drive from Hamilton)
Want to witness another natural phenomenon? Make a push to Point Pelee National Park to see the mysterious migration of monarch butterflies that converge here in autumn. Located near Leamington on Lake Eerie (Cleveland is due south across the water), Point Pelee is the southernmost point of the Canadian mainland. It’s only 40 miles southeast of Windsor, where you can drive the Ambassador Bridge — the busiest international crossing in North America — to Detroit.
Go beyond the city — go northeast for autumn leaves and countryside
Prince Edward County (126 miles/2-hour drive)
When driving from Toronto northeast on Highway 401, take time to check out the fall foliage in Scarborough Bluffs Park (11 miles/30-minute drive). Walk among 11 parks (Sylvan Park has a trail to the lakefront) strung along nine miles of bluffs, which are significant geological features some 12 millennia old.
Prince Edward County, aka “The County” in local parlance (learn some charming “county-isms before you go), is a rural region with nine communities surrounded by 500 miles of shoreline. This sanctuary for wine-makers, farmers, and artists (take a studio tour in September) seems like it has been suspended in time —in a good way. Life is serene and it’s all about enjoying simple pleasures.
Sink your teeth into housemade pork sausage at Flossie’s Sandwich Parlor in the town of Picton, shop for antiques in the Carriage Barn at Hickory Tree in Bloomfield, and take a cheese-making workshop at Littlejohn Farm, where you can even stay the night. If you prefer a lakeside view and fireplace, opt for the Owner’s Suite at The Drake Devonshire (an outpost of the Drake Hotel in Toronto). The massive A-frame room has floor-to-ceiling windows on the water.
Kingston (57 miles/1-hour drive)
With its picturesque perch along the St. Lawrence River and swaths of sandy beaches, you might be tempted to spend your time in Kingston strolling the waterfront and soaking up the views. Go deeper on a self-guided tour of “limestone city” — named for the stone from which its historic buildings were constructed — to see the stomping ground of Canada’s first prime minister, Sir John A. Macdonald. Then imagine military life in the 19th century, complete with the sound of canyons firing and drums beating. Get the full-on experience by firing a Snider Enfield rifle at Fort Henry. This National Historic site is salso part of the Rideau Canal and Kingston Fortifications System that have been recognized as a UNESCO World Heritage site.
Kingston’s arts community is thriving too. Support the literary world during Kingston WritersFest, held over five days at the the end of September. More than 60 writers and 50 literary events promise to deliver enthralling and interactive experiences (readings, conversations, and performance) for all visitors. Hear the voices of diverse writers from various cultures and orientations, including Indigenous and Metis talents from Canada.
If you’re hungry, pop over to the Kingston Public Market to meet local artisans and farmers and buy treats to take home like maple syrup and honey. Ontario’s oldest market, it was established in 1801 and since then has been a community gathering place for the city. With so much to discover in this bustling city, it’s a great idea to make your base downtown. Immerse yourself in the historic Hochelega Inn, an 1879 French Victorian-style mansion features 21 unique and cozy suites, plus complimentary breakfast and an on-site boutique brimming with treasures crafted by locals.
Plan your next trip to Ontario on the Travel Ontario website.