Above: Old Quebec Photo: Ken Wiedemann

Traveling to a foreign country from Chicago is remarkably easy—and you can do it in the comfort of your own car, no less—with Canada’s nearest entry point just beyond Detroit.

Cross the border and cruise through the vast provinces of Ontario and Quebec, wending your way from diverse Toronto to chic Montreal and then, finally, to the picturesque capital nationale, Quebec City, on a 1,120-mile journey that increases in exotic appeal the farther north you go.


The route that stitches together this string of waterfront cities traces the scenic shores of several Great Lakes and, to the east, that of the steely St. Lawrence River, which eventually pours into the Atlantic. After zipping through Michigan’s Harbor Country, you’ll cut straight across central Michigan, flying by Kalamazoo and Ann Arbor before arriv- ing in Detroit.

You’ll cross into Canada via the Detroit- Windsor Tunnel, which dips 75 feet below the Detroit River and goes for a mile before depositing you on the other side. Passports out! The route hugs the coast of Lake Ontario and then the banks of the St. Lawrence River as you motor from Toronto toward Montreal in the French-speaking province of Quebec.

Heed highway signs in French—remember that stop signs read “Arrêt”—and take in the majestic scenery along the way: bridges and harbor fronts, the 764-foot Mount Royal, dark-green forests, and endless tributaries. From its commanding cliffside perch, the famously walled Quebec City, one of the oldest European settlements in North America, has the power to transport. Where am I and where will I go next? Ponder the answers over a bowl of café au lait at an outdoor coffee shop with a view of the seaway.

Where to Stop Along the Way



Chicago → Detroit: 285 miles, 4.5 hours
Eat Endure the line at Avalon International Breads (avalonbreads.net), because the artisanal breads, jams, and sea salt cookies are worth the wait.
Shop At Shinola (shinola.com), objects made with pride in Detroit include watches, custom bicycles, and a slew of handcrafted goods, from footballs to American flag sets. At Pure Detroit in the Fisher building (puredetroit .com), you’ll find bottle stands and butcher blocks made by Reclaim Detroit (reclaimingdetroit.org), which recycles materials salvaged from the city’s teardowns.
See Take advantage of special late-night programming on Fridays at the Detroit Institute of Arts (dia.org), where you should experience the majesty of Diego Rivera’s massive Detroit Industry murals.
Lodge The Corktown neighborhood is home to the coveted two-bedroom Honor & Folly (honorandfolly.com; rooms from $165), likely for its cool, homey atmo- sphere and smattering of locally crafted tchotchkes.


Detroit → Toronto: 231 miles, 4 hours
Eat Dive into the bustling St. Lawrence Market (stlawrencemarket.com) and line up for the peameal- bacon sandwich, thickly sliced hamlike pork served on a crusty bun at cash-only Carousel Bakery.
Do Inspect the original Stanley Cup bowl, the pièce de résistance of the Hockey Hall of Fame (hhof.com), which you can eyeball in Lord Stanley’s vault. The city hosts WorldPride (worldpridetoronto.com), billed as North America’s largest pride event, from June 20 to 29.
Lodge The 259-room Four Seasons Hotel Toronto (fourseasons.com; rooms from $396), glamming up the already glittery Yorkville neighborhood, scores with a stunning wood-centric design, suite-like standard rooms, and Café Boulud from the Michelin-starred French chef Daniel Boulud.
Seventy-five miles southeast of Hamilton and the southern coast of Lake Erie, which you hit en route to Toronto, lies the dramatic crown jewel of the Great Lakes system: Niagara Falls. More than 750,000 gallons of water plummet over the 167-foot cataract every second, generating 4.4 billion watts of power. Get drenched on one of two new 700-passenger catamarans (niagaracruises.com) replacing the Maid of the Mist boats—on the Canadian side of the falls only—starting in May.



Toronto → Montreal: 336 miles, 5.5 hours
Eat At the woodsy new Manitoba (facebook.com/restomanitoba) in Little Italy, old-timey Canadian cuisine shows up on plates featuring smoked fish, game, plants, and wild mushrooms.
Do Leave your maps behind and follow local artist Cam Novak on a bike tour of street art (camnovak.com) through the city—including Plateau Mont-Royal, the Mile-End, and Boulevard St. Laurent—to find its best graffiti and public art. Visit from June 12 to 15 and explore gigantic, colorful spreads created by 35 artists at the free Mural Festival (muralfestival.com).
Lodge Opened in March, the minimalist 154-room Alt Hotel Montreal Griffintown (montreal.althotels.ca/en; rooms from $136), constructed of reclaimed bricks and aluminum panels, offers breathtaking picture-window views over the city.


Quebec City

Montreal → Quebec City: 155 miles, 2.5 hours
Eat Save the sit-down meal for dinner at Panache at the Auberge Saint-Antoine (see below) and instead browse the indoor stalls of the Marché du Vieux-Port (marchevieuxport.com) for artisanal breads and cheeses, seasonal crab, and ice cider.
Drink Quench your thirst with the refreshing ales and lagers at the Bar Le Sacrilège (lesacrilege.com), a cool neighborhood watering hole where you might catch a live radio broadcast.
Do Find a bench on the Dufferin Terrace and watch nightly fireworks on the banks of the St. Lawrence River. From June 12 to 15, during Rendez-Vous Naval de Québec (rendezvousnaval.com), legions of Canadian and foreign sailors pull into port.
Lodge Set within the walls of the old city, the 95-room Auberge Saint-Antoine (saint-antoine.com; rooms from $245) showcases an 18th-century façade, old finds from the original building—a maritime warehouse—and the elegant yet rustic dining room at Panache.