Around the world, municipalities have been making substantial investments into broadband access infrastructure to accelerate the build-out of an urban phenomenon that has become known as a smart or connected city. At the 2016 Optical Fiber Communications Conference, a team contest, the Connected OFCity Challenge, was held to discuss the technological innovations and to examine dependencies and intricacies of a connected city project. The participants, four teams of experts coming from a cross-section of the industry, presented and defended their visions of future applications and innovative architecture and technologies to realize the interconnection. This paper provides a synthesis of the four competitive proposals offered for the contest and their ensuing discussions.