Eat like a king at 529 Wellington Steakhouse, the city’s toniest steakhouse housed in an elegant riverside mansion. Good steak is what it’s all about here. Waiters show off the alluringly marbled cuts on white platters, whisking from one table to another with their “tour of beef”: ribsteak, porterhouse and filets. Deftly executed gravies—bearnaise, hollandaise, cognac peppercorn, marrow and rossini—turn premium slabs of meat into masterpiece meals.
Location: 529 Wellington, 204-487-8325
Heavy wooden doors only a few steps from Portage and Main open onto a world that celebrates the British Empire at Bailey’s. This rare enclave of cloth-bedecked tables and classic cooking seems like one of the last bastions of traditional fine dining. Yet, despite the luxury of the surroundings, a genuine warmth pervades. The space is welcoming, the service impeccable, and the dining room rings with laughter from nearby tables. The star of this restaurant’s fine dining menu is the prime rib, a decadently buttery pink slab lying under a puff Yorkshire pudding.
Location: 185 Lombard Ave, 204-944‑1180
Clay Oven’s locations in the South End and at Shaw Park—overlooking the field where the Goldeyes play ball—know how to make a statement. Sleek dining rooms are styled with hanging glass baubles, mod lighting fixtures, and clean-lined tables and seats; dishes may arrive to the table still sizzling on a roaring hot cast iron platter or releasing wafts of fragrance from an elegant scrolled metal dish. Vibrant, colourful curries, charred naan and meats kissed by the high-heat tandoori oven make for a richly spiced feast fit for any celebration.
Locations: 1 Portage Ave E, 204-982-7426; 240-1600 Kenaston Blvd, 204-888-2529
This classy country estate houses The Gates on Roblin, the perfect backdrop for birthdays and anniversaries. The restaurant, with a total capacity of 300+, offers a selection of dining rooms, like the original dining room perfect for intimate groups of 12, or the spacious sunroom accommodating up to 72 guests at a time. Score a seat in the Atrium and enjoy breathtaking views alongside elegantly-prepared regional fare like bison short ribs and duck confit.
Location: 6945 Roblin Rd, 204-224-2837
A tried and true classic Winnipeg establishment for 60 years, Hy’s Steakhouse is located at the city’s famous Portage and Main intersection and is the place to go when looking for an opulent, New York-style dining experience. The atmosphere is comfortably elegant with traditional dark paneling spread throughout its three levels. An apt menu of perfectly aged steaks, Canadian prime rib, and a newer selection of dietary-conscious items, like meatless meatloaf, ensures every guest leaves the dinner table happy.
Location: 1 Lombard Place, Main Floor Richardson Building, 204-942-1000
Chef/owner Fern Kirouac has been serving Winnipeg his palate-expanding Meditteranean-slanted French cuisine since opening InFerno’s Bistro in the city’s French quarter in 2003. Today, foodies still flock to the cozy, refined yet relaxed spot for longtime menu favourites and revelatory daily specials alike. A two-storey space divided into several rooms, the restaurant has a feeling of intimacy that makes every occasion feel special. Try one of six variations on moules et frites, twirl your way through a plate of house-made pasta or sample saucier expertise with an entrée like duck confit with orange gastrique. Warning: the pastry case strategically placed by the entrance is hard to ignore.
Location: 312 des Meurons St, 204-262-7400
Kum Koon Garden is the grand dame of Winnipeg’s Chinatown restaurants, a massive 650-seat dining room where dim sum becomes an event and any meal feels like a banquet. Servers push carts stacked with steamer baskets of Cantonese specialties, including a mind-boggling array of steamed and fried dumplings, savoury packets of rice paper and wonton wrappers that look like little works of art. Steamed buns stuffed with saucy barbeque pork, slabs of taro root cake, and crispy fried shrimp dumplings beckon—be sure to go on an empty stomach.
Location: 257 King St, 204-943-4655
This downtown spot is decked out in chic furnishings and nods to the vibrancy of Mexico, including a colourful gallery wall and an array of more than 40 types of tequila. La Roca’s menu is elevated yet crowd-pleasing, with 11 different taco options from meaty carnitas to panko-fried avocado slices. Mains like juicy carne asada steak or blackened rainbow trout—served with a zesty salsa verde—provide a bounty of flavour for larger appetites. Perfect for a mid-week family dinner, or a more raucous celebration Thursdays through Saturdays when live music is on offer.
Location: 115 Smith St, 204-615-9605
Maxime’s, a south Winnipeg favourite, sets the standard for suburban-style fine dining. Spherical lighting reminiscent of tangled ribbon graces the grand room, while fireplaces add warmth and soft carpeting amps up the cozy factor. Maintaining its decades-old tradition, this multi-generational spot plates plenty of classic western European dishes—veal parmesan, chicken slouvaki, lamb chops—served alongside a newer selection of continental dishes with Asian flair.
Location: 1131 St. Mary’s Rd, 204-257‑1521
Tucked into a South End strip mall, Nicolino’s is the sleek and chic destination for contemporary Italian cuisine that celebrates local produce and ingredients from the motherland in equal measure. A mod, open dining room with tables generously spaced makes it easy to lounge and revel in a celebratory meal. What comes from the kitchen is revelatory as well: crostinis topped with locally-sourced wild boar and sharp Romano, pillowy gnocchi and salmon crisped in a golden layer of brown sugar are highlights.
Location: 4-2077 Pembina Hwy, 204-269-5004
This family-run favourite opened in 1977 and has been in its Marion Street location for more than 20 years. Pasquale’s is a classic red-sauce joint, from checkered table covers and memorabilia from Italia down to the perfectly executed staples of Nonna’s comfort cooking. The warm space is ideal for family occasions, elevated Sunday suppers and candle-lit date nights alike. Sublime pastas range from traditional—hello, spaghetti frutti di mare—to more contemporary options like Sambuca cream sauce spiked with chile, and veal and chicken entrées are splurge-worthy dishes that go easy on the wallet.
Location: 109 Marion St, 204-231-1403
Upscale regional cuisine gains an earthy flair at this idyllic, cottagey restaurant inside Pineridge Hollow, a beautiful turn-of-the-century carriage house converted to a shopping and dining destination and events space. Start with celebratory vino and craft cocktails inside the elegant dining room, touched with just a hint of rustic whitewash and cute decor. Some classics are classic for a reason—that’s why you’ll find crispy house-made beet chips and a pot of goat cheese ranch dip on nearly every table. Prairie proteins are gracefully prepared and typically paired with hyperlocal produce pulled from the on-site garden.
Location: 67086 Heatherdale Rd 25E, Oakbank, MB, 204-777-3881
An historic railway station and train car have been transformed into one of the most elegant ways to experience French cuisine in Winnipeg. The retrofitted train car at Resto Gare boasts plush velvet seating and white tablecloths that harken back to an era of ritzy dining cars. Inside the station, a clean, modern dining room makes use of industrial-chic touches of dark wood and stone, and a cozy fireplace. In either setting, signatures like escargots in a pool of rosemary garlic jus or rich duck cassoulet topped with maple bacon chutney are sure to make the meal a memorable one.
Location: 630 Des Meurons St, 204-237-7072
A downtown favourite for the pre-Jets game crowd, Rudy’s Eat and Drink hits the sweet spot between creature comfort and upscale dining. Patterned wallpaper, plush upholstery and leather accents offer the decor equivalent of a menu that is both indulgent and refined: homey mac n’ cheese appears as croquettes spiked with Mornay and pesto, while ramen is transformed from budget bite to a chopped salad topped with tiger prawns. Old school cocktails, quality steaks and midcentury preparations (chicken cordon bleu, pork schnitzel) reignite our love for the pomp and circumstance of dining out.
Location: 375 Graham Ave, 204-421-9094
New-school fine dining is epitomized at Smith Restaurant inside Inn at the Forks, where elevated flavour and culinary technique meet simplicity and unfussy comfort. The kitchen’s ethos of celebrating history and land is reflected in a dining room replete with Canadiana: Hudson’s Bay blanket banquets, deer antler chandeliers, archival photography and touches of woodsman plaid. Prairie proteins like Arctic char and rabbit (both sourced in-province) get special treatment on the regionally focused menu, and Canadian beef shines as a cut of steak or an expertly seasoned tartare.
Location: 75 Forks Market Rd, 204-944-2445
Chef Nitin Sharma has stacked the dinner menu at Velvet Glove Restaurant with local producers and seasonal ingredients in sophisticated applications. Local bison tataki is a beautifully presented array of thinly sliced, lightly seared loin served with tangy ponzu soy sauce on a bed of mustard cress. The restaurant’s elegant dining room is wrapped in the hotel’s original warm wood paneling, tables are dressed in white linen, and the service remains impeccable.
Location: The Fairmont Hotel, 2 Lombard Pl, 204‑957‑1350
