Friday
- 8:00 PM
Pizzeria Gusto
Date night · $$ · AcademyKick the night off — Wood-fired pies, natural wine, intimate Academy Rd. corner.
Why this pick- ·Built for a real boys' night — high energy, late hours
- ·Keeps you in Academy — short walk from your other stops
- ·A fall-perfect atmosphere
- 10:00 PMSous SolNightlife · Osborne Village
Cocktail bar — Speakeasy-style basement room, classic cocktails done right.
Why this pick- ·Built for a real boys' night — high energy, late hours
- ·Keeps you in Osborne Village — short walk from your other stops
- ·A fall-perfect atmosphere
- 12:00 AMCentre Culturel Franco-ManitobainCulture · Saint-Boniface
Francophone theatre, gigs and films — pair with a stroll through old Saint-Boniface.
Why this pick- ·Built for a real boys' night — high energy, late hours
- ·Keeps you in Saint-Boniface — short walk from your other stops
- ·A fall-perfect atmosphere
Saturday
- 12:00 PM
Bismillah Restaurant
Brunch · $$ · South OsborneRecovery brunch — Halwa puri brunch — Pakistani breakfast on weekends — line-up worthy.
Why this pick- ·Built for a real boys' night — high energy, late hours
- ·Keeps you in South Osborne — short walk from your other stops
- ·A fall-perfect atmosphere
- 3:00 PMThe Park TheatreNightlife · Osborne Village
Live music — Restored 1915 cinema turned mid-size live venue.
Why this pick- ·Built for a real boys' night — high energy, late hours
- ·Keeps you in Osborne Village — short walk from your other stops
- ·A fall-perfect atmosphere
- 12:30 AMTimes Change(d) High & Lonesome ClubNightlife · St. Boniface side of Main
Honky-tonk, blues and roots seven nights a week — tiny, sweaty, legendary.
Why this pick- ·Built for a real boys' night — high energy, late hours
- ·Keeps you in St. Boniface side of Main — short walk from your other stops
- ·A fall-perfect atmosphere
Sunday
- 1:00 PM
Stella's Café (Sherbrook)
Brunch · $$ · West BroadwaySlow brunch — Eggs Stella — Local mini-chain brunch institution, packed Sundays.
Why this pick- ·Built for a real boys' night — high energy, late hours
- ·Keeps you in West Broadway — short walk from your other stops
- ·A fall-perfect atmosphere
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