The market was started with a loan from the town of Carrboro.
During the course of 2006, some local residents expressed annoyance at new rules stating that all performances on the market lawn must have signed permission in advance from the owners of Carr Mill Mall. The lawn area consistently holds events and entertainment.
In May 2007, plans were announced to open a third store in Hillsborough, North Carolina and move the market's food preparation operations to Hillsborough for greater efficiency. Even though the plans were announced in May 2007, plans and employee feedback were included in the decision-making process since 2006. About 100 workers presented a petition in opposition to the plan outlining their concerns that WSM was growing too large.
Plans have been made in other locales to copy the success of Weaver Street Market; one example is in Boynton Beach, Florida.