Stretch your arms and legs. Pack some cheese and crackers. And throw away your guidebook! The French spirit abounds in Montreal, and there is no better way to soak up that spirit than wandering down its many charming avenues, with the city’s cool mountain air filling your lungs and relaxed atmosphere truly bringing serenity to your mind. But unlike its European counterparts, this gem of French Canada is a hilly, undulating city. In fact you’ll often see sophisticated Montrealers on their way to dinner parties in hiking boots! A good pair of shoes is a must in this Canadian mountain town, no matter how easy it is to forget you’re not in Europe.
If you’re the kind of traveler who likes to get a taste of the daily life of the locals, stay away from the touristy monuments and stroll down any of these five elegant side streets. The beauty of the quaint townhouses, churches, and old theaters of the residential districts will enchant you. The grandeur of the spacious boulevards of Downtown will give you a sense of Montreal’s prosperous history. And don’t be embarrassed to wear even the clunkiest hiking boots with a Prada suit or Miu-Miu gown; the Quebecois will have it no other way!

1. Avenue du Mont-Royal Est
Walk west along this bohemian street in the Plateau district in the late afternoon. You will have a wonderful view of the Parc du Mont-Royal and the famous illuminated crucifix that adorns its peak. The Plateau is a low-rent haven for many college students who attend McGill University during the day and frequent the many independently owned boutiques, bookstores, and pubs on the Avenue at night. A popular DVD/video store turned cultural institution, La Boîte Noir sure to delight those of French avant-garde cinematic tastes. This bustling street is the best place to see Montreal’s young and artistic hipster scene.

2. Chemin Cote-Ste.-Catherine
Two affluent neighborhoods bunt heads in Montreal’s northern districts, and no trip can be without a visit to the snootier, more traditional, Francophone neighborhood of Outremont. For those seeking a quieter, more private stroll, the refined ambiance and towering mansions along the Chemin Cote-Ste.-Catherine are bound to impress you.
Home to a thriving Hassidic community, many of the townhouses display a regal Jewish architecture, making Outremont a sort of cleaner, wealthier, French version of Brooklyn. The restaurants of Outremont are exclusive and unwelcoming dens of caviar and martinis. So be sure to pack your top hat and opera glasses!

3. Avenue Sunnyside
The best views of the city can be seen from this avenue in the neighborhood of Westmount. That is, if you can see past the stately stone facades of the many manors that line this steep incline just south of its rival neighborhood, Outremont.
Perhaps because the area is populated by mostly English-speakers, the architecture is reminiscent of New England Gothic, with thickets of ivy growing over carved archways and colossal mahogany gates. On early mornings, the fog that collects in the Parc Mont-Royal flows over Westmount as it descends into the St. Laurence river basin. A walk at this time will leave you mesmerized by the eeriness of Montreal’s old money and tradition.

4. Passarelle du Cosmos
A short distance from the iconic Biosphere on Ste. Helene island, the Passarelle du Cosmos is a small bridge in the lush Parc Jean-Drapeau. On the outskirts of the city proper, the thicket of trees in the Parc grows denser and the mystical St. Laurence river rages and churns swiftly down a heavily wooded ravine. A walk across the river on the passarelle places you face-to-face with Montreal’s surrounding wilderness. You gain the sense that you’ve stumbled upon a hidden oasis in the middle of an untamed North American forest. In fact, Canada’s vast acreage of untouched back country is what lends Montreal its adventurous character. Your soul will be set free!

5. Rue St. Antoine Est
The lights, the cafes, the theaters and restaurants! Downtown Montreal is why you came to Quebec in the first place, and Rue St. Antoine is at the heart of it all. But it’s a calm street at night, which is the perfect time to stroll down the cobblestone lanes that wind between the elegant high-rises. As you wander up on the Hotel de Ville and the Palais du Congres, sheaths of blue and orange light spill from the windows and street lamps. The Victorian architecture, with its touches of Canadian ruggedness, awes you, as the street musicians that play their violins and trumpets late into the night rouse your heart strings. Finish of your trip with this glamorous burst of light and beauty! It’s the most romantic street in town and will bring joyful tears to the eyes of even the most weathered globe trotter.