Friday
- 8:00 PM
Deer + Almond
Global small plates · $$$ · ExchangeKick the night off — Inventive, dim, the city's tasting-menu darling.
Why this pick- ·Built for a real boys' night — high energy, late hours
- ·Keeps you in Exchange — short walk from your other stops
- ·A shoulder-season favorite
- 10:00 PMThe Rec RoomFamily · Entertainment district
Arcade, axe throwing, virtual sports and shareable plates — works rain, snow or shine.
Why this pick- ·Built for a real boys' night — high energy, late hours
- ·Keeps you in Entertainment district — short walk from your other stops
- ·A shoulder-season favorite
- 2:00 AM
Segovia
Spanish tapas · $$ · OsborneLate-night fix — Tiny room, sherry, jamón.
Why this pick- ·Built for a real boys' night — high energy, late hours
- ·Keeps you in Osborne — short walk from your other stops
- ·A shoulder-season favorite
Saturday
- 12:00 PM
Clementine
Brunch · $$ · ExchangeRecovery brunch — Best brunch on the prairies, line by 9.
Why this pick- ·Built for a real boys' night — high energy, late hours
- ·Keeps you in Exchange — short walk from your other stops
- ·A shoulder-season favorite
- 3:00 PMAssiniboine ParkOutdoors · Tuxedo
Gardens, the Leaf conservatory, free outdoor theatre.
Why this pick- ·Built for a real boys' night — high energy, late hours
- ·Keeps you in Tuxedo — short walk from your other stops
- ·A shoulder-season favorite
- 8:30 PM
Across the Board Game Café
Café / Comfort · $ · Exchange1,000 board games, sandwiches and milkshakes.
Why this pick- ·Built for a real boys' night — high energy, late hours
- ·Keeps you in Exchange — short walk from your other stops
- ·A shoulder-season favorite
- 12:30 AM
Bar-hop the district
Pick the busiest nightlife strip and crawl three rooms — sports bar warm-up, cocktail lounge, then dance floor.
Want a different vibe?
Try one of the other ready-made Winnipeg plans.