The glorification of the manicured lawn is a result of a colonial history of English landscape practices that were adopted in North America. As climate science and evidence of biodiversity loss are now at the forefront of public policy, environmentalists and ecologists are questioning the value of the lawn that has been engrained into North American society. The evolution of weed and grass by-laws in municipalities across Ontario tend to limit property owners’ and occupants’ rights to express environmental and cultural beliefs through the planting of natural landscapes that differ from the traditional-style lawn. This paper examines the City of Toronto Municipal Code Chapter 489, Grass and Weeds, which is compared and contrasted with five North American municipalities property standards and weed and grass by-laws. The by-law is challenged and questioned against the City’s environmental strategies that promote alternative landscaping practices. This paper is intended to provide insightful recommendations on how the City of Toronto and other similar municipalities can revise their weed and grass by-laws through a proposed model by-law intended to support environmental stewardship.