Montréal City Guide: Metropolis + Mountains (and Poutine!)

By KEEN Adventure Guide Chelsea Parrett
Montréal, a charming city nestled in the southeastern corner of Canada’s province of Quebec, somehow finds the perfect juxtaposition of a budding creative metropolis with old-school allure. It has big city feels, like New York City, but with some seriously adorable French charm.
Cobblestone streets next to graffiti-lined walls and carefully curated cafés on each corner, this city is filled to the brim with history and expression—the perfect backdrop for a KEEN Elsa winter boot adventure.
The fascinating thing about wandering Montréal is that each neighborhood has its very unique look and feel, and you’ll constantly find yourself in new corners of the city that feel like you’ve entered a whole new world.
Here are some favorites to check out…
Rue St. Paul: The “Old Montréal”
Wander the streets and learn a little history about the city, but also to find some time for Montréal’s snack staple: POUTINE (you won’t regret it!). Also, if you get the chance, head over to the tiny French Café Le Petit Dep for a 5-star Cappuccino and the cutest tiny market.
Mile End: As HIP As It Gets
Legend says this is where the term “hipster” originated, and it’s not hard to see why. This neighborhood is equal parts down-to-earth brownstones/narrow alleyways to its plethora of trendy bars and restaurants with an artist’s touch. Everything you come across here is cool cool cool.
Mount Royal Neighborhood and Park: An Oasis in the City
What feels so special about the Mount Royal area is its dose of nature that blends beautifully with the unique architecture of the neighborhood. Find yourself walking the streets with brightly colored Victorian homes and up the winding steps leading you to some of the most epic views of the city. This ancient volcano-turned-city-park is a must-see landmark in Montréal — don’t miss the sunrise hike to the top.
Chelsea (left) in a Chelsea, part of the Elsa insulated boot collection for women. Also available in Canada in the Belleterre collection.
CAFÉ CULTURE
Looking for somewhere to relax with a cup of coffee and a pastry? Montréal is home to some of the most beautifully designed cafes out there, it’s hard not to come across stunning conceptual designs and spaces. Here are a few to get you started…
Mélisse
Tommy Café & Apero
Ginkgo Café
Kamehameha
MOUNTAIN ESCAPE
Not only does Montréal offer expansive city views and limitless neighborhood exploration, it’s also home to some incredible trails, outdoor spaces, and quick-trip destinations nearby.
Tremblant Mountain: A Winter Wonderland
With just a 1.5-hour drive, you’ll find yourself in the center of what feels like a winter wonderland, Tremblant Mountain. This ski resort and pedestrian village is a great way to explore nature and enjoy a relaxing day in the snow. With miles of hiking trails, ski runs, and a colorful pedestrian village of shopping and restaurants, this is the perfect way to end a Montréal adventure.
Portlander Chelsea Parrett is a self-described “professional slash-y" working as a photographer, stylist, and art director. Follow along on her adventures on Instagram at @chelseaparrett.