The word nightcap may have become a euphemism for a little tonsil hockey—as in “wanna come up for a nightcap?”—but there is still a place for the late night drink, whatever it is called. No matter how good the food and service, few restaurants can hold your attention for more than a couple of hours, and if you and your date are not ready to head home, then the nightcap is the perfect end to the evening. If you are out with the guys and the din of the latest JT hit and the glare of too many big screen TVs has become too much, a quiet, relaxed libation is just the thing to calm that throbbing head.

Tradition rules when it comes to nightcaps. Scotch, cognac, vodka, or a martini are your choices. You might get away with something smoother like Baileys or Kaluha, but you might want to avoid the cocktail that is actually called a Nightcap—a questionable blend of scotch, crème de cacao and milk.
So, where is a guy to go to get a late night drink in this town? Despite the resurgence of the martini and scotch crowd, Winnipeg doesn’t boast a lot of intimate drinking spots. If you are looking for a place with atmosphere, intimacy, and a bartender who knows how to make a bone dry martini, your choices are limited. But those places are out there and they are worth tracking down.

G Martini
As the name suggests, the drink of choice here is the martini. G Martini has established itself as an Osborne Village institution with its range of colourful martinis, from traditional standards to chocolate banana concoctions like the Curious George. With its dim lighting, cozy atmosphere and friendly staff, it certainly fits the bill as a great late night spot.

The Current Lounge
Winnipeg boasts some excellent hotel lounges—The Fairmont and the Palm Room at the Fort Garry for example—but the sleekest is the lounge at the Inn at The Forks. Late night jazz, stylish and classy interior and excellent bar food make this space a standout. The bartenders push their Caesars, but the well-stocked bar has just about everything the late night imbiber could want.

Rae and Jerry’s
Be careful where you walk in this Winnipeg institution because you’ll trip over a cliché. The movie Swingers did more to rehabilitate the idea of the nightcap than any number of Ocean remakes, and Rae and Jerry’s could have been a location for that film. The age of the crowd gets younger as the night gets older. With its red leather, dark oak and fifties retro-chic vibe, it’s money, baby!

Cafe 22
Located at the west end of the Corydon strip, Cafe 22 gets overlooked by the tourists and gelatti hunters. But with its cool lighting and seating it’s the perfect place to wrap-up an evening and spend a comfortable hour relaxing. Its discreet booths are just the thing if you are looking for something more intimate. Food is pretty good, too, and their pizzas are one of the city’s hidden culinary gems.

Hy’s
A hangout for the city’s suits and power players. Most people come for the famous steaks in the restaurant, but the lounge has developed its own reputation and the high-ceilinged bar has one of the largest selections of scotch in the city. It can be a little stiff, but the place comes alive on Friday and Saturday nights when the ties get loosened and martini shakers get shaking.