A new hybrid quiz-reality show will test teams on their knowledge of Toronto’s evolving streetscapes. When Did They Build That? premieres on the Real Estate & Development Outreach (REDO) Network today.

The two-part challenge begins with an in-studio trivia round to pose questions about place names, iconic addresses and historic site occupancies. Action then ramps up when contestants move outdoors for the obstacle course and scavenger hunt, in which they race to complete a checklist of tasks while navigating construction detours, traffic congestion and ever-changing cartography.

REDO’s managing producer, N. Phil Denzetti, explains the concept came to him last fall when he took his skates to be sharpened, only to find that the retail block he’d been patronizing for decades had been transformed into the podium of a 55-storey condominium tower.

“As it turns out, the outdoor rink was actually remade into a micro off-leash dog park,” he recounts. “So what I really needed was a Yorkshire Terrier.”

The new show fits into REDO’s lineup of fact-based urban fun and drama, which includes favourites such as: the rapid-round quiz match, What’s My Zone?; the travelogue and lifestyles review, Day-trippers’ Guide to Legal Non-conforming Uses; and the compelling view of homeowner aspirations and the frailties of neighbourliness uncovered in Cross-Ontario Committee of Adjustment Highlights.

“If there are 8 million stories in the naked city, there’s got to be a billion stories, not to mention storeys, in an elaborately outfitted one,” Denzetti asserts. “REDO’s mission is to assess and develop that potential. We are confident there are still heights to hit, depths to plumb and a missing middle to flesh out.”

He also hints there will be more cinéma vérité efforts in the near future. Last year, the documentary, The Mistaking of the Residents — following the non-occupant owner, Victor Jamais, through his 12th consecutive unsuccessful bid to get elected to his condo corporation’s board of directors — was one of REDO’s top streaming requests and also won the 2021 Property Managers’ Choice Award.