While it used to be said that downtown rolls up its sidewalks at five, that hasn't been true for Calgary in over 20 years.
Downtown has a couple of areas to head for a drink: Eau Claire,
the Stephen Avenue "Walk", and the bottom of pretty well any office tower.
Along Stephen Avenue, there has been a hubbub of places opening up in some of Calgary's oldest heritage buildings east of First Street:Wine-Oh's, James Joyce Pub, Bank & Baron PUB, and Saltlik's & the Sky Bar. If you want to impress your business associates there are two places to consider: the very classic Thompson's in the Hyatt Hotel, and the Fairmont Palliser Hotel's Oakroom Lounge (in the lobby).
West of First Street where all the office towers cluster, e there's Earl's in Bankers Hall,
and across the street is the lounge in the Metropolitan Grill (very popular with the oil patch executives),
the patio at Local Bar and Grill, and National On 8th (with rooftop patio)
Moving west, are Barcelona Tavern (formerly Belgo Brasserie), and at 6th Street and 7th Street (by the Uptown and Globe theatres) are several establishments including Barcelona Tavern (formerly Belgo Brasserie), and Ceili's Irish Pub.