Maritime trade has influenced the historic growth trajectory of many Indian cities. Spices, along with scents and silks, were central to world trade for thousands of years. The urban landscape of the cultural regions of Kozhikode (Calicut) and Kolkata on India's Coast demonstrates its maritime global trade history which in turn contributed to the making of these Cities and the pluralistic expression. Both of these maritime cities have played a significant role in the wider Indian Ocean history through their prominent roles in international trade. This deep hybrid history associated with trade has led to a heterogenous city fabric which was produced over centuries of socio-economic transactions contributing to the evolution of the urban form of these port cities. On a closer analysis, the cosmopolitan expression is evident through the evolution of its market streets, ethnic community neighbourhoods, inter-diasporic exchanges and socio-cultural institutions. The historic market streets of these city cores act as memoirs of global spice and goods trade, events and exchanges. The paper aims to explore the urban evolution of these cultural landscapes through two important historic wholesale markets namely Valiyangadi in Kozhikode and the Bara Bazar in Kolkata. These markets have been important trading posts of the colonial powers witnessing the trading relations of spice, silk and other goods. The inquiry sets out a comparative spatial reading of urban form evolution and changing dynamics of these important market streets within the inner-city cores. Findings reveal that the port and trade relations along these markets were the catalysts in the transformation of the city and the evolution of its present urban form. The present situation also points towards the changing urban dynamics of these market networks within the city which are still anchoring the cultural expression of these cities.