Let’s start this easy:

What is the longest road entirely contained within the limits of the City of Montreal?

First one with the correct answer gets a free hug.

UPDATE: Correct answer below. Gouin Blvd., the longest street on the island, runs through Pierrefonds, Ste. Geneviève, Roxboro, Cartierville, Ahuntsic, Montreal North and Rivière des Prairies before ending at Sherbrooke Street near the eastern tip of the island (a total of five boroughs).

Senneville Road extends Gouin Blvd. west into Senneville and around the western tip to Ste. Anne de Bellevue, but it’s not counted in this trivia question.

Only Sherbrooke St. sees more borough action, crossing through Côte-des-Neiges/NDG, Ville-Marie and then straddling the borders of Plateau Mont-Royal, Rosemont-Petite-Patrie and Mercier/Hochelaga-Maisonneuve before ending in Pointe aux Trembles/Rivière des Prairies (6 total). In between it stops in the independent cities of Montreal West, Montreal East and Westmount. There are also separate, unconnected Sherbrooke Streets in Lachine and Beaconsfield.

The bonus question, whether one can drive from one end to the other uninterrupted, is also correct below. The street is one-way through eastern Ahuntsic, and oncoming traffic meet at de Lorimier Ave., forcing a detour toward Henri-Bourassa Blvd.