The success of a city’s retail core is largely dependent on the composition and organization of its merchant constituents. Not only should the price-point and products of a city’s retail align with its resident and visitor demographics but the stores should be strategically balanced to maximize consumer spending and interest. Heritage destinations dependent on the tourism market should pay special attention to this issue, assuring their visitors a valuable shopping experience while simultaneously preserving the destination’s cultural appeal. This case study considers the rapidly evolving shopping district of Charleston, South Carolina, focusing specifically on the retail core’s recent influx of chain merchants to what was once predominantly a local main street. A historical account, paired with an in-depth survey of merchants, is presented. The research builds on previous studies that have considered the issue of merchant mix from the perspective of the city’s stakeholders, tourists, and residents.