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Weekend plan

Date Night in Winnipeg — Curated for Two

Rooftop cocktails, low-lit dinners, jazz at 10 — paced like a real night out.

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Friday

  1. 6:30 PM
    BDI (Bridge Drive-In)
    Food & Drink · Riverview

    Iconic ice-cream walk-up by the river — Goog Special is a Winnipeg rite of passage.

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    Why this pick
    • ·Date-night ready — low-lit, cocktail-paced
    • ·Keeps you in Riverview — short walk from your other stops
    • ·A fall-perfect atmosphere
  2. 8:00 PM

    Pizzeria Gusto

    Date night · $$ · Academy

    Low-lit dinner — Wood-fired pies, natural wine, intimate Academy Rd. corner.

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    Why this pick
    • ·Date-night ready — low-lit, cocktail-paced
    • ·Keeps you in Academy — short walk from your other stops
    • ·A fall-perfect atmosphere
  3. 10:30 PM
    St. Norbert Farmers' Market
    Food & Drink · St. Norbert

    Saturday market with prairie producers, food trucks and live music — May–Oct.

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    Why this pick
    • ·Date-night ready — low-lit, cocktail-paced
    • ·Keeps you in St. Norbert — short walk from your other stops
    • ·A fall-perfect atmosphere

Saturday

  1. 11:00 AM

    Bismillah Restaurant

    Brunch · $$ · South Osborne

    Slow brunch — Halwa puri brunch — Pakistani breakfast on weekends — line-up worthy.

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    Why this pick
    • ·Date-night ready — low-lit, cocktail-paced
    • ·Keeps you in South Osborne — short walk from your other stops
    • ·A fall-perfect atmosphere
  2. 4:00 PM
    The Park Theatre
    Nightlife · Osborne Village

    Live music — Restored 1915 cinema turned mid-size live venue.

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    Why this pick
    • ·Date-night ready — low-lit, cocktail-paced
    • ·Keeps you in Osborne Village — short walk from your other stops
    • ·A fall-perfect atmosphere
  3. 11:00 PM
    Forks Market Food Hall
    Food & Drink · The Forks

    Two-storey food hall with global stalls and a rooftop deck — always-open bored fix.

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    Why this pick
    • ·Date-night ready — low-lit, cocktail-paced
    • ·Keeps you in The Forks — short walk from your other stops
    • ·A fall-perfect atmosphere

Remix

Want a different vibe?

Every plan below is freshly built from Winnipeg's top curated picks.