1. What to Know

Montreal got its start way back in 1642, at a time when New York was still New Amsterdam and Philadelphia was still decades from existing. Initially called Ville-Marie, Montreal was established at Pointe-à-Callière, where the St. Lawrence River met what was then the Petite Rivière. In 1992, when Montreal celebrated its 350th birthday, the Pointe-à-Callière Museum opened on this very spot, the culmination of more than a decade of archaeological digs at the site. The museum, actually a sprawling complex of buildings, houses more than a million artifacts (many of which are displayed in their original locations) and traces centuries of area history from Amerindian days to the present. For a quick starter course in Montreal's heritage, check out the museum's excellent 18-minute large-screen multimedia show, Yours Truly, Montréal.

2. Where to Go

Fittingly, Old Montreal—and indeed, most of modern Montreal—fans outward from its origins here. Just steps to the west is the famed Notre-Dame Basilica, a grand Gothic Revival church built in the 1820s on an original site from 1657, with a massive century-old pipe organ inside and gorgeous stained glass revealing scenes from Montreal's religious history. The next-door Old Sulpician Seminary, dating from 1685, is the city's oldest building.

To the east is the Vieux-Port (or Old Port), no longer Montreal's main commercial harbor but today a busy waterfront recreation area, including a recently added urban beach. To the south is the Centre d’Histoire de Montreal, with 3 floors of exhibitions revealing the many shades of the city's story, all set within its renovated central fire station.

To the north is Place Jacques-Cartier, a spot that served as a marketplace even prior to European settlement and is now one of Montreal's most bustling tourist areas, lined with outdoor cafés and filled with street performers. Nearby are both Champ-de-Mars Park, site of the longest remaining section of the city's early fortification wall, and Château Ramezay, Quebec's oldest private history museum, set in the 1705 residence of a former governor of New France, and featuring a beautiful French colonial style garden.

3. Where to Browse

But Old Montreal has far more on offer than just history—it's also one of the city's hottest areas for art and shopping. Local philanthropist Phoebe Greenberg is the force behind 2 of the neighborhood's most exciting new art institutions, the DHC/ART gallery on St. John Street and the multi-disciplinary Centre Phi exhibition and performance space on St. Pierre Street.

Around the corner from the latter along St. Paul Street are many of Montreal's hippest clothing boutiques, including Denis Gagnon (headquarters for the local fashion icon of the same name), Cahier d'Exercices (selling eclectic women's runway designs from around the world), Michel Brisson (with its stylish suits and streetwear for men) and Reborn (offering a curated collection of international labels for both women and men).

4. Where to Eat

Over the past 15 years, Old Montreal's dining options have gone from limited at best to downright boundless—indeed, this is now the city's top restaurant neighborhood. From Olive & Gourmando's scrumptious breakfasts and lunches to the gourmet market/eatery Le Cartet to the modernized fine French fare at Le Club Chasse et Pêche and Les 400 Coups, Old Montreal is brimming with culinary excitement and excellence. Also here are Garde Manger and Le Bremner, both local favorites helmed by Iron Chef America winner and native Montrealer Chuck Hughes.

5. Where to Stay

Likewise the stellar hotel line-up in Old Montreal makes it one of the city's most desirable districts for overnighting. Hotel Nelligan (named for Quebec's answer to Arthur Rimbaud, poet Émile Nelligan) offers boutique luxury at the heart of the 'hood, and a rooftop terrace with fantastic views of the Old Port and all of Old Montreal. Just steps away is the superb all-suite Le Saint-Sulpice, while down the block on fashionable St. Paul Street is the romantic Le Petit Hotel. Around the corner is the refined Auberge Bonaparte, where some rooms even overlook Notre-Dame's private gardens.

6. What Not to Miss

Speaking of Notre-Dame, a great way to round out your Old Montreal visit is with a quick stop at the historic square across the street, Place d'Armes. Taking its name from its 1-time role as the city's main military staging area, the square is now protected by a staff-wielding (and pigeon-beloved) monument to Montreal's founder, Paul de Chomedey, Sieur de Maisonneuve. When he first landed nearby in 1642, little could Maisonneuve have envisioned that so many centuries later, he'd still be watching over this dynamic neighborhood that just keeps getting better.