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The Winnipeg Walkway System, also known as the Winnipeg Skywalk, is a network of pedestrian skyways and tunnels connecting a significant portion of downtown Winnipeg, Manitoba. The City of Winnipeg described the Walkway as a system of 14 skyways and 7 tunnels connecting 38 buildings and allowing for a maximum protected walk of 2 km. The system also provides year-round climate-controlled access to over 170,000 m2 (42 acres) of space, including over 200 shops and businesses, 10 office complexes, 60 restaurants and snack bars, 700 apartment units, 2 hotels, 11 financial centres, and the Winnipeg Millennium Library, bringing together 21,000 employees. The walkway system has expanded since its initial construction.The Walkway is subdivided into four interconnected segments: its skyways chiefly cover Portage, Graham, and St. Mary Avenues; and its underground section includes Winnipeg Square and the underground Portage and Main concourse.It is open every day of the week, typically from 06:30 AM to 12:30 AM, though some individual building hours vary.

CJUM-FM (101.5 FM, UMFM) is a volunteer-driven campus radio station in Winnipeg, Manitoba, Canada, based at the University of Manitoba and transmits with 1,200 watts from an antenna located at Portage and Main in downtown Winnipeg.

201 Portage (formerly TD Centre, Canwest Place, and CanWest Global Place) is an office tower at the northwest intersection of Portage and Main in Winnipeg, Manitoba, Canada. It is the 2nd tallest building in Winnipeg and in the province of Manitoba.

Downtown Winnipeg is an area of Winnipeg located near the confluence of the Red and Assiniboine rivers. It is the oldest urban area in Winnipeg, and is home to the city's commercial core, city hall, the seat of Manitoba's provincial government, and a number of major attractions and institutions. The City of Winnipeg's official downtown boundaries are: the Canadian Pacific Railway mainline on the north, Gomez Street and the Red River on the east, and the Assiniboine River on the south; the western boundaries of downtown are irregular, following along a number of different streets, back lanes, and across properties. Generally speaking, the western boundaries are rarely further west of Balmoral and Isabel Streets. In 2016, Canadian Geographic produced a map that generalize Winnipeg's downtown boundaries.Neighbourhoods in the downtown area include the Exchange District, Central Park, The Forks, and Chinatown. The downtown area is roughly 3 square kilometres (740 acres). Winnipeg Square, Canada Life Centre, Portage Place, and the flagship store of The Bay (closed 30 November 2020) are all located on the downtown section of Portage Avenue. On Main Street are Winnipeg's City Hall, Union Station, and the Manitoba Centennial Centre, which includes the Manitoba Museum, the Planetarium, the Centennial Concert Hall, and the Winnipeg Railway Museum. Although over 60,000 people work downtown, only 13,470 people actually live in the Downtown area.There are several residential projects under construction on Waterfront Drive and in the Exchange District, and the residential population of the area is projected to increase substantially in the next few years.

The Richardson Building is a 34-storey office tower at the intersection of Portage and Main in Winnipeg, Manitoba, Canada. The building forms the anchor of the Lombard Place development, and is connected to Winnipeg Square shopping mall via the Portage and Main Concourse. The thirty-four storey building stands 124 metres tall (407 ft), making it the (behind 201 Portage and 300 main) third tallest building in Winnipeg. It is dressed in granite chip pre-cast concrete and solar bronze double-glazed glass.In 2011, the CBC moved its digital television transmitters for CBWT-DT and CBWFT-DT to the Richardson Building, on a new antenna that raised the pinnacle of the building to 151.8 metres (498 ft), once again making it the tallest structure in Winnipeg.

360 Main is a 32-storey office tower located near Portage and Main in downtown Winnipeg, Manitoba.It is connected to the Winnipeg Square underground mall and the Winnipeg Skywalk. 360 Main & Shops of Winnipeg Square comprises 597,755 square feet of leasable area, of which 55,284 square feet is the retail component of Winnipeg Square. The property has 954 parking stalls. Currently owned by Artis REIT, a real estate investment trust from Winnipeg, the building was originally home to the Winnipeg Commodity Exchange and was known as the Commodity Exchange Tower. Although the naming rights expired in 1990, it was not officially renamed to 360 Main until 2010. Throughout this time, it has been unofficially known as the Trizec Building.

Winnipeg Square (also known as the Shops of Winnipeg Square) is an underground shopping mall located at Portage and Main in downtown Winnipeg, Manitoba, Canada. It was built in 1979 by Smith Carter Parkin for the Trizec Corporation, and has 45 stores and restaurants. It also includes the 300 Main apartment block, 330 Main surface level retail complex (both under construction), and the 360 Main Commodity Exchange Tower (also known as the Trizec Building). Winnipeg Square is connected to the Winnipeg Walkway through the Concourse which links all four corners of the city's main office district via an underground roundabout. It has been estimated that 16,000 people pass through Winnipeg Square each weekday.

Heritage Winnipeg Corporation is a non-profit charitable organization in Winnipeg, Manitoba, that works to save and redevelop the city's built heritage.

No. 1 Northern is a large public art work in the form of a steel abstract sculpture by John Cullen Nugent, currently standing where it was originally installed in the fore court of the Canadian Grain Commission building in Winnipeg, in 1976. The work generated controversy from the moment it was unveiled, and even after its removal by ministerial order in 1978. In 1979, Meriké Wiler called it the most controversial piece of Canadian public art ever commissioned during the fourteen years of Canada's public art funding scheme. It was hauled away and cut into pieces on two occasions, before and after being installed in front of another federal government building, and finally reinstalled at its intended location once more in 1997, nearly twenty years after its removal.

Artis Reit Residential Tower, or 300 Main, is a multi-family residential high-rise building Main Street in Winnipeg, Manitoba, Canada. At 42 stories it is the tallest building in Manitoba.Located at the intersection of Portage and Main in downtown Winnipeg, the building is connected to the Winnipeg Skywalk system, as well as other assets owned by Artis REIT, including 330 Main and the Winnipeg Square parkade. On its first floor will be an Earls restaurant, moving from down the road near The Forks.This building, together with 300 Main and 360 Main, now spans almost an entire city block. It is the first-ever residential building to be located at Portage and Main. As of March 2021, at just above 128 metres (420 ft), the yet-to-be-complete structure already stands higher than the 201 Portage building, which has been Winnipeg's tallest tower since 1990.

The Winnipeg Fringe Theatre Festival is an alternative theatre festival held each year for twelve days in July in Winnipeg, Manitoba, Canada.

The Mitchell Block (also known as the Gillett Building or the Grange Building) is a three-storey structure at 173 McDermot Avenue in the Exchange District of Winnipeg, Manitoba, Canada. Built in 1886/87 for the W. J. Mitchell Drug Company, the first drug store in Winnipeg, it is now a municipally-designated historic site.Designed by architect Arthur T. Timewall, the building includes a mortar and pestle above the doorway, and an ornamental scroll was engraved along the roofline, which gave it a distinction among the other buildings at the time it was constructed.Today, the building houses an Italian bistro called The Mitchell Block.