You could spend an entire Toronto visit in the downtown core, walking between attractions like the Hockey Hall of Fame, Ripley’s Aquarium, and Rogers Centre, home of the Toronto Blue Jays.
But don’t stop there. This dizzyingly diverse megalopolis is, at its heart, a collection of neighborhoods with their own cultures and character, such as restaurant-heavy Harbord Village and shopping hub the Annex. And unlike downtown, where chain brands dominate, independent shops, restaurants, and hotels are alive and well in these urban villages. Which is exactly how locals like it. Home-grown establishments are prized here, and Torontonians are fiercely protective of neighborhood haunts.
Here are some of our favorite neighborhoods to explore. (Can’t pick just one? Toronto is an immensely walkable and bikeable city—rent one of Bike Share Toronto’s cycles and hop from one neighborhood to another using the city’s 530 miles of bike lanes.)
The Annex
Best for: Architecture walks and casual eats
About two miles northwest of the core, the Annex spans from Bloor Street north to Dupont Street between Bathurst Street and Avenue Road. Its streets reflect both its wealth and long history as a hangout for University of Toronto students. Head to Bloor Street for a mix of bookstores, ramen joints, vintage stores, and coffee shops, or go to Dupont for local favorites like the splashy Middle Eastern Fet Zun and upscale taqueria Playa Cabana. Catch touring bands at Lee’s Palace, Bloor’s grungy and beloved concert hall. And don’t skip the side streets, which boast pristine Regency revival and Victorian homes, including late urbanist Jane Jacobs’s beautiful Edwardian on Albany Avenue and Margaret Atwood’s place on Admiral Road.
Where to stay
Book now: The Jane
Proprietor Jane Harvey’s edgy art collection graces the Jane; the six suites of this bed-and-breakfast are outfitted in a style we might call Victorian-Italian-modern. Expect to see pieces from American photographer Larry Sultan and Canadian contemporary artist Joanne Tod.
Bloorcourt Village
Best for: A night out
Once a sleepy residential neighborhood dotted with dive bars, Bloorcourt Village has become Toronto’s buzziest strip for those looking for dinner and dancing. You’ll find Civil Liberties, where bartenders create on-the-fly custom cocktails; Paradise Grapevine, with hard-to-find wines, Ontario beers, and local ciders; and seafood-forward gastropub Chantecler, which recently relocated from Parkdale. There’s also chef Jesus Morales’s acclaimed Nicaraguan restaurant, La Bella Managua, and Tallboys, with Toronto’s largest selection of Ontario craft tallboy cans and solid burgers, wings, and salads. Later, dance the night away at music club the Piston, whose disco-themed Fridays are a must.
Where to stay
Book now: Annex Hotel
While Bloorcourt lacks lodgings, the nearby indie Annex Hotel, painted black with loft-like rooms, sets you minutes from the strip. Its Wine Bar is an ideal place to unwind with a biodynamic wine or the perfect gin martini.
Danforth Music Hall hosts a range of acts, including French music producer and artist Madeon, pictured here.
Photo by Aron Harris arichardphoto/Shutterstock
Greektown
Best for: Food and music adventures
Danforth Avenue—the Danforth to locals—anchors the city’s east-end Greektown. And while the established neighborhood now hosts brewpubs alongside tavernas, there’s still plenty of Greek flavor. Fridays and Saturdays are Greek music nights at modern eatery Soula’s, and the aroma of loukoumades, or Greek doughnuts, wafts from Athens Pastries. The Danforth is also heaven for music lovers, with record stores and musical-instrument shops lining the street. Dig through the crates at KOPS Records, Toronto’s oldest indie record shop, and take in a show at the intimate Danforth Music Hall, a one-time cinema where acts run the gamut from comedy shows to rock concerts.
Where to stay
Book now: Canopy by Hilton Toronto Yorkville
Hotel options near Danforth Avenue are slim. The modern-yet-cozy Canopy by Hilton Toronto Yorkville is only a 15-minute walk from all the action.
Find French classics with a local spin at Parquet.
Photo by Daniel Neuhaus
Harbord Village
Best for: Discovering hot new chefs
To get to Harbord Village, enjoy the walk west from Queen’s Park through the University of Toronto’s gorgeous neo-Gothic campus. You’ll land on Harbord Street, one of Toronto’s most happening restaurant rows. At newcomer Parquet, chef Jeremy Dennis riffs on French classics with local provisions—think cassoulet with Ontario pork. And Piano Piano touts phenomenal pizza and pasta, like the lush mushroom cavatelli. After dessert, stroll to nearby Major Street to drool over some of Toronto’s most beautiful—and priciest—Victorian homes. Note the laneways named for local notables, such as activist Leah Cohen and playwright David French.
Where to stay
Book now: Park Hyatt
The very glam, just-reopened Park Hyatt situates you less than a mile north of Harbord Street.
Kensington Market
Best for: A classic Toronto feel
Toronto’s onetime Jewish immigrant hub has evolved into a laid-back cobble of vintage shops, fishmongers, cocktail bars, and restaurants. Only one synagogue remains, but an old-school vibe prevails, thanks to locals’ successful crusades against chain stores and property development.
Don’t miss chef David Schwartz’s sexy Sunny’s Chinese, hidden in the Kensington Mall indoor shopping arcade, and wine bar Gray Gardens, a favorite for secret sake menus and unfussy small plates. The boutique Bungalow offers midcentury-modern furniture and clothes from brands like Kuwalla and Obey, and the Oud & the Fuzz is an Armenian bar and live-music venue that serves cocktails spiked with Armenian pomegranate juice and dishes like eetch (bulgur) salad.
Where to stay
Book now: Hotel Ocho
On foot, Kensington Market is just 10 minutes north of Chinatown’s industrial-chic Hotel Ocho.
Riverdale Park in Leslieville is a favorite for skyline views.
Photo by AevanStock/Shutterstock
Leslieville
Best for: Small-town feel
Stretching east of the Don River on Queen Street, low-slung Leslieville feels like a village within the city. It’s a must for travelers looking to bring something local back home: Scout offers home goods, jewelry, body products, and paper goods from Canadian makers, and Province of Canada sells long-lasting cotton essentials like striped pocket T-shirt dresses. For the cocktail curious, check out family-owned Reid’s Distillery, which sells its gin in Signature, Spiced, and Citrus varieties. A quick cab ride north drops you in the 44-acre Riverdale Park, with running tracks and skyline views that make it a favorite of Leslieville residents.
Where to stay
Book now: The Broadview
The Broadview, a former strip club, is now a high-design, low-profile hotel with the city’s best roof deck.
Little Portugal/Dundas Street West
Best for: The art lover
There’s still a Portuguese tang to this west-side neighborhood, with restaurants like Chiado, which specializes in “progressive Portuguese” cuisine such as grilled tiger shrimp with piri piri and an assorda soup with lobster and clams. But Little Portugal has also become an art and retail center. Stop at next-gen newsstand Issues to pick up a unique indie magazine, which you can peruse with a coffee at espresso temple Hamers Coffee. Continue your journey browsing the choice photography collection at Stephen Bulger Gallery, then strolling through 36-acre Trinity Bellwoods Park, where locals picnic and play on warm weekends.
Where to stay
Book now: Ode
Little Portugal’s hyper-stylish, compact Ode, one of Toronto’s few Black-owned boutique hotels, features commissions from Toronto artists in each of its rooms.
The Drake Hotel is a popular and historic boutique hotel, restaurant, and cafe in Parkdale.
Photo by Paul McKinnon/Shutterstock
Parkdale
Best for: A bit of everything
An only-in-Toronto kind of neighborhood, Parkdale mashes up galleries, indie shops, and artisan bakeries, along with restaurants catering to its large Tibetan population. Shop Matt Robinson’s elevated military-inspired men’s designs at Klaxon Howl, then take home a Toronto-made bauble from Made You Look, which showcases 100 local designers. Elaine Fleck Gallery displays top-tier Toronto artists like photographer Pengkuei Ben Huang and digital creator Brandon Steen, and the famous Milky Way laneway, aka Graffiti Alley, is a constantly changing outdoor “gallery” of street art. Sunset your Parkdale journey at Pretty Ugly, with one of its mezcal-forward craft cocktails.
Where to stay
Book now: The Drake Hotel
Built in 1890 and renovated in 2004, the 51-room Drake Hotel pioneered Parkdale’s artsy transformation—a sleek new wing opened last year.
