Friday
- 7:00 PM
Segovia Tapas Bar
Date night · $$$ · Osborne VillagePatio kickoff — Tiny Spanish room, share plates and sherry — best small date spot in town.
Why this pick- ·Outdoor pick — built for fresh-air time
- ·Keeps you in Osborne Village — short walk from your other stops
- ·A fall-perfect atmosphere
- 8:30 PMPatricia BeachOutdoors · Lake Winnipeg — 1h NE
Long, quiet sand spit — locals' alternative to Grand Beach.
Why this pick- ·Outdoor pick — built for fresh-air time
- ·Keeps you in Lake Winnipeg — 1h NE — short walk from your other stops
- ·A fall-perfect atmosphere
Saturday
- 9:00 AMAssiniboine ParkOutdoors · Tuxedo
Gardens, the Leaf conservatory, free outdoor theatre.
Why this pick- ·Outdoor pick — built for fresh-air time
- ·Keeps you in Tuxedo — short walk from your other stops
- ·A fall-perfect atmosphere
- 1:00 PM
Bismillah Restaurant
Brunch · $$ · South OsborneOutdoor lunch — Halwa puri brunch — Pakistani breakfast on weekends — line-up worthy.
Why this pick- ·Outdoor pick — built for fresh-air time
- ·Keeps you in South Osborne — short walk from your other stops
- ·A fall-perfect atmosphere
- 3:00 PMRed River Mutual TrailOutdoors · The Forks
World-record holder: longest naturally frozen skate trail.
Why this pick- ·Outdoor pick — built for fresh-air time
- ·Keeps you in The Forks — short walk from your other stops
- ·A fall-perfect atmosphere
- 6:00 PMForks Market Food HallFood & Drink · The Forks
Two-storey food hall with global stalls and a rooftop deck — always-open bored fix.
Why this pick- ·Outdoor pick — built for fresh-air time
- ·Keeps you in The Forks — short walk from your other stops
- ·A fall-perfect atmosphere
- 8:00 PM
Pizzeria Gusto
Date night · $$ · AcademyWood-fired pies, natural wine, intimate Academy Rd. corner.
Why this pick- ·Outdoor pick — built for fresh-air time
- ·Keeps you in Academy — short walk from your other stops
- ·A fall-perfect atmosphere
Sunday
- 9:00 AMAssiniboine Park & English GardenOutdoors · Assiniboine Park
Walk — Golden-hour stroll through the gardens and Leo Mol sculpture park.
Why this pick- ·Outdoor pick — built for fresh-air time
- ·Keeps you in Assiniboine Park — short walk from your other stops
- ·A fall-perfect atmosphere
- 1:00 PM
Deer + Almond
Global small plates · $$$ · ExchangeInventive, dim, the city's tasting-menu darling.
Why this pick- ·Outdoor pick — built for fresh-air time
- ·Keeps you in Exchange — 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.
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