Discover the Authentic Toronto Through Its Must-See Neighborhoods

You could easily fill your Toronto itinerary with the downtown core, hopping between attractions like the Hockey Hall of Fame, Ripley’s Aquarium, and the Rogers Centre, where the Toronto Blue Jays play.

But don’t stop at downtown. This vibrant metropolis is fundamentally a tapestry of neighborhoods, each with its own unique culture and charm—like the restaurant-rich Harbord Village and the shopping-centric Annex. Unlike downtown, where chain stores reign, these urban enclaves are bustling with independent shops, eateries, and hotels, exactly as locals prefer. Home-grown businesses are cherished here, and Torontonians fiercely defend their beloved local spots.

Here are some of our top neighborhood picks to explore. (Can’t decide on just one? Toronto is incredibly walkable and bike-friendly—rent a bike from Bike Share Toronto and glide from one neighborhood to another along the city’s 530 miles of bike lanes.)

The Annex

Ideal for: Architectural strolls and casual dining

Located about two miles northwest of downtown, the Annex stretches from Bloor Street to Dupont Street, nestled between Bathurst Street and Avenue Road. Its streets showcase both affluence and a rich history as a popular spot for University of Toronto students. Explore Bloor Street for a blend of bookstores, ramen spots, vintage shops, and cozy cafés, or visit Dupont for local gems like the vibrant Middle Eastern Fet Zun and the upscale taqueria Playa Cabana. Don’t miss Lee’s Palace, Bloor’s gritty yet cherished concert venue, and wander the side streets to admire beautiful Regency revival and Victorian homes, including the charming Edwardian once owned by urbanist Jane Jacobs on Albany Avenue and Margaret Atwood’s residence on Admiral Road.

The Jane, owned by Jane Harvey, features an edgy art collection; its six suites are styled in a mix we could call Victorian-Italian-modern. Look out for works by American photographer Larry Sultan and Canadian contemporary artist Joanne Tod.

Bloorcourt Village

Perfect for: A lively night out

Once a quiet residential area filled with dive bars, Bloorcourt Village has transformed into Toronto’s hottest spot for dinner and dancing. Discover Civil Liberties, where bartenders whip up custom cocktails on demand; Paradise Grapevine, featuring rare wines, Ontario beers, and local ciders; and the seafood-centric gastropub Chantecler, which has recently moved from Parkdale. Don’t miss chef Jesus Morales’s renowned Nicaraguan restaurant, La Bella Managua, and Tallboys, home to Toronto’s largest selection of Ontario craft tallboy cans alongside delicious burgers, wings, and salads. Later, groove the night away at the music club the Piston, famous for its disco-themed Fridays.

Where to Stay

While Bloorcourt doesn’t have accommodations, the nearby indie Annex Hotel, adorned in black with spacious loft-style rooms, is just minutes from the action. Its Wine Bar is the perfect spot to relax with a biodynamic wine or an expertly crafted gin martini.

Greektown

Ideal for: Culinary and musical explorations

Danforth Avenue—affectionately called the Danforth by locals—serves as the heart of the city’s east-end Greektown. This well-established neighborhood now features brewpubs alongside traditional tavernas, but it retains its rich Greek character. On Friday and Saturday nights, enjoy Greek music at the trendy eatery Soula’s, while the sweet scent of loukoumades, or Greek doughnuts, drifts from Athens Pastries. Music enthusiasts will feel at home here, with record stores and musical-instrument shops lining the avenue. Explore the collection at KOPS Records, Toronto’s oldest indie record shop, and catch a show at the cozy Danforth Music Hall, a former cinema that hosts everything from comedy to rock concerts.

Where to Stay

Accommodations near Danforth Avenue are limited. The stylish yet inviting Canopy by Hilton Toronto Yorkville is just a 20-minute stroll from all the excitement.

Harbord Village

Perfect for: Exploring exciting new chefs

To reach Harbord Village, enjoy a pleasant walk west from Queen’s Park through the stunning neo-Gothic campus of the University of Toronto. You’ll arrive at Harbord Street, one of Toronto’s vibrant restaurant hotspots. At the trendy Parquet, chef Jeremy Dennis puts a fresh spin on French classics using local ingredients—imagine cassoulet made with Ontario pork. Meanwhile, Piano Piano serves outstanding pizza and pasta, including rich mushroom cavatelli. After dessert, take a stroll to nearby Major Street to admire some of Toronto’s most stunning—and expensive—Victorian homes. Don’t miss the laneways named after local figures, like activist Leah Cohen and playwright David French.

Where to Stay

The stylishly renovated Park Hyatt is located less than a mile north of Harbord Street.

Kensington Market

Ideal for: Experiencing a classic Toronto atmosphere

Once the heart of Toronto’s Jewish immigrant community, this area has transformed into a relaxed maze of vintage shops, fish markets, cocktail bars, and eateries. Only one synagogue remains, yet the old-school charm persists, thanks to locals’ efforts to fend off chain stores and large-scale developments.

Be sure to check out chef David Schwartz’s stylish Sunny’s Chinese, tucked away in the Kensington Mall indoor shopping arcade, along with the wine bar Gray Gardens, known for its secret sake selections and simple small plates. For midcentury-modern furniture and clothing, visit the boutique Bungalow, featuring brands like Kuwalla and Obey.

Where to Stay

Kensington Market is just a 10-minute walk north of Chinatown’s trendy industrial-chic Hotel Ocho.

Leslieville

Ideal for: A quaint, small-town vibe

Extending east of the Don River along Queen Street, the charming, low-rise Leslieville feels like a cozy village in the heart of the city. It’s a must-visit for travelers wanting to take home something local: Scout features home goods, jewelry, body care products, and stationery from Canadian artisans, while Province of Canada offers durable cotton staples like striped pocket T-shirt dresses. For cocktail enthusiasts, family-owned Reid’s Distillery provides gin in Signature, Spiced, and Citrus flavors. A short cab ride north leads you to the expansive 44-acre Riverdale Park, boasting running paths and skyline views that are a hit with Leslieville locals.

Where to Stay

The Broadview, once a strip club, has transformed into a stylish, understated hotel featuring the best rooftop deck in the city.

Little Portugal/Dundas Street West

Ideal for: Art enthusiasts

This west-side neighborhood still carries a hint of Portuguese culture, highlighted by restaurants like Chiado, known for its “progressive Portuguese” dishes, such as grilled tiger shrimp with piri piri and a rich assorda soup with lobster and clams. Additionally, Little Portugal has blossomed into a hub for art and retail. Swing by the innovative newsstand Issues for a unique indie magazine to enjoy with a coffee at Hamers Coffee, the local espresso haven. Continue your adventure by exploring the impressive photography at Stephen Bulger Gallery, then take a leisurely stroll through the 36-acre Trinity Bellwoods Park, a favorite spot for picnics and play during warm weekends.

Where to Stay

The chic, compact Ode in Little Portugal is one of Toronto’s few Black-owned boutique hotels, featuring art commissions from local Toronto artists in each room.

Parkdale

Ideal for: A little bit of everything

Parkdale is a uniquely Toronto neighborhood that blends galleries, indie shops, and artisan bakeries, alongside eateries that serve its vibrant Tibetan community. Explore elevated military-inspired men’s fashion by Matt Robinson at Klaxon Howl, then pick up a locally crafted piece from Made You Look, featuring 100 local designers. The Elaine Fleck Gallery showcases leading Toronto artists like photographer Pengkuei Ben Huang and digital artist Brandon Steen, while the famous Milky Way laneway, also known as Graffiti Alley, serves as a dynamic outdoor “gallery” of street art.

Where to Stay

Originally built in 1890 and updated in 2004, the 51-room Drake Hotel played a key role in Parkdale’s artistic revitalization—a sleek new wing was added just last year.