Photograph by Catherine Karnow
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A couple sneaks a kiss on top of Mount Royal, the city's namesake.
Photograph by Catherine Karnow

Quebec's largest city moves in cycles of cool. One was between Expo 67 and the 1976 Olympics (where Nadia scored her perfect 10). It’s in full stride again with musicians from Mile End and chefs from spruced-up Old Montreal at the top of their game. Take it all in, then use the mountain the city was named after—Mount Royal—as a trou normand (palate cleanser). Chef Caroline Dumas produces her signature soups in Mile End, sells them in Old Montreal, and walks to work via Mount Royal—“how I visualized Montreal as a kid,” Dumas says. “Seen from above, Montreal is not very big. It’s a city on a very human scale.”

When to Go: Late June for the Jazz Festival to see how loosely the term is interpreted (from classics like Oliver Jones to folkie Martha Wainwright, both Montreal natives); August for the Osheaga Music and Arts Festival; and February for Montreal en Lumière, one of the world’s largest winter festivals, attracting 900,000 hearty revelers each year. The citywide food, wine, and arts celebration includes menus prepared by top international chefs and a packed performance schedule that features artists from Diana Krall to The Zombies and free outdoor concerts.

Where to Stay: Sleep in refurbished charm in Old Montreal at Hotel Nelligan, Hotel Le St-James, Pierre Du Calvet (built in 1725), and the St-Paul Hotel. Fairmont The Queen Elizabeth is known as the hotel where John Lennon and Yoko Ono recorded “Give Peace a Chance” in room 1742 and staged one of their two “bed-ins” for peace in 1969. While the hotel is currently closed for renovations, it will reopen in June 2017.

How to Get Around: First opened in 1966, Montreal’s metro still feels swinging with its molded plastic artsy vibe. Locals find the name silly, but the Underground City’s pathways are convenient during bitter winter days.

What to Do Before You Go: Watch C.R.A.Z.Y. (2005), read or watch Mordecai Richler’s The Apprenticeship of Duddy Kravitz, and listen to Arcade Fire, which first ignited while key members lived in Mile End.

Mile End

What to Do: This is where Canadian author Mordecai Richler grew up, along with other hardscrabble Jewish, Italian, Irish, Greek, and Québécois kids. Visit Wilensky’s Light Lunch to be transported back in time and experience authentic Montreal smoked meat—the cured, smoked, and gently steamed beef brisket cousin of New York pastrami. Order a Wilensky’s Special (all-beef bologna and salami on a grilled roll), and don’t ask to hold the mustard or slice it in half. The signature sandwich has been served the same way since 1932, and that’s part of what makes it so special.

Where to Eat or Drink: Compare the bagels at Fairmount and St-Viateur. Comptoir 21 serves top-notch fish and chips on a shiny wooden counter. Nouveau Palais kept the diner décor, tweaked the food, and added a DJ to brunch.

What to Buy: Drawn and Quarterly for comic and art books, without the attitude. Savoie Fils for fine men’s clothes and accessories, and high-end toiletries and shaving supplies. (There’s also an uber-hip Café Myriade coffee bar inside.) Find out-there curios and revolving exhibitions at Monastiraki.

Mount Royal

What to Do: Montrealers have made a mountain of this hill, which serves as an anchor geographically and for the soul. In the winter, toboggan or skate on Beaver Lake. On summer Sundays, the slopes attract drummers, dancers, and curious onlookers. Jog up the many paths for a view of downtown or to see the landmark, LED-lit cross close-up.

Where to Eat or Drink: Santropol sandwiches are where gourmet meets hippie. Avoid the perennial line at Schwartz’s by ordering smoked meat—medium, never lean—for take-out, then picnic on the mountain. In summer, the food trucks near the Cartier monument change daily.

Old Montreal

What to Do: Built over architectural remains, Pointe-à-Callière provides a foundation on the history of Montreal. The Marché Bonsecours is an open, indoor market of eateries and made-in-Quebec boutiques. Look for hidden squares, like the one at Gibby’s.

Where to Eat or Drink: SoupeSoup’s name doesn’t say it all: the bestseller is pouding chômeur (poor man’s pudding), a classic Québécois dessert. Le Club Chasse et Pêche serves the spoils of the hunt, as imagined by urbanites. At Olive et Gourmando the attitude can be a bit snooty, but the creative sandwiches (like the roasted tofu Viva Las Vegan or The Cubain roasted pork panini) are what you’ll remember.

What to Buy: Designer Denis Gagnon is known for his deft hand with leather. Cahier d’Exercices’ space is as chic as the clothes. Zone Orange has quirky knickknacks.

What to Read Before You Go: Bone and Bread (House of Anansi Press, 2013). “A love letter to Montreal” is how native daughter Saleema Nawaz describes her novel about two teenage sisters living atop a bagel shop in the city’s Mile End neighborhood.

Helpful Links: Official guides to Old Montreal and the Old Port

Fun Fact: Montreal got with the times and ended a 66-year ban on food trucks in June 2013. Streetfood MTL has an app and trucks tweet their locations.

Nyka Alexander was born in Ottawa, raised in Montreal, and lives in Toronto when she isn’t becoming more Canadian by traveling abroad.