Jacques Cartier knew a good thing. On Oct. 2, 1535, the French explorer, impressed by a triple-peaked hill on an island sited at the confluence of the St. Lawrence and Ottawa rivers, named it Mont Royal. That eventually morphed into Montréal. Even today, it’s hard not to be impressed by the island city’s landscape. Every season has its pluses, but autumn, when the city’s 1,000 parks glow with fiery reds, oranges and golds, is especially ideal.

Wake up to Montréal on the morning Downhill All the Way bicycle tour with Fitz & Follwell. The guided cruise begins near the summit of Frederick Law Olmstead-designed Mount Royal Park, winds down through forests and by Beaver Lake, and finishes in the flat terrain of the Plateau neighborhood. En route, receive an overview of the city’s history, heritage and landmarks and enjoy breakfast at Café Santropol before finishing around 11 a.m.

Soak in the architecture and ambience of Old Montréal while browsing the galleries and boutiques lining Rue Saint-Paul, the city’s oldest street. For exceptional sandwiches, salads and baked goods, duck into Olive + Gourmando. At the nearby Pointe-à-Callière Montréal Museum of Archaeology and History, built upon the site where French missionaries landed in 1642, pad through six centuries of history and heritage in the archaeological crypt.

Jump to present-day Montréal along Rue Sainte-Catherine, the city’s main shopping thoroughfare; or descend to the Underground City, a 20-mile network with approximately 1,700 shops, 200 restaurants and 40 movie theaters. Emerge on Rue Sherbrooke and window-drool the boutiques lining the Miracle Mile to the Montréal Museum of Fine Arts.

Plan to arrive at the 185-acre Montréal Botanical Garden at least an hour before sunset to explore the arboretum and specialty gardens in full autumn glory, but save the Chinese and Japanese gardens for nightfall. If your visit falls in September and October, traditional lanterns transform both into mystical spectacles.

Ready for dinner? Once an industrial neighborhood, Saint-Henri is gentrifying, and Le Smoking Vallée, a bring-your-own-wine restaurant, is getting a lot of buzz. Afterward, get jazzed at Upstairs Jazz or House of Jazz, both legendary clubs.

Seal the day with a pilgrimage to one of two Montréal institutions for a midnight snack: Schwartz’s, Canada’s oldest deli, for a smoked meat sandwich (don’t forget the fries and pickle); or St-Viateur Bagel for a hand-rolled bagel baked in a wood-fired oven. Go ahead, pick up a dozen as a souvenir, but don’t be surprised if they disappear before you arrive home.