The Indian shopping experience is undergoing a drastic shift from brick and mortar to click and order. The anytime anywhere medium Internet is playing a distinctive role in opening up novel opportunities in how business is being done. The world's largest retailer Wal-Mart's buying 77% equity stake in India's e-tail major Flipkart for the US $16 bln is an indicator of the transformation e-commerce industry is undergoing in India. Technology has bought transformations and also some scepticism related to risk and uncertainty on certain aspects of online transactions. Organised retailing accounts for 8% of an approximately 600 billion USD dollar market. There is a tremendous scope of growth if we compare the Indian economy to the other South East Asian markets. The macro-environment too suggests that India is poised for uninterrupted growth in the coming years. The rural foray of retailers can also prove to be the strategic initiative giving good results. Amazon says that 70% of its business is coming from small towns which aptly points to the fact that if challenges of rural distribution and communication are met revenues can significantly be driven up. The current study makes an attempt to explore the variation in factors affecting online shopping among rural and urban customers and also identify the significant factors affecting online shopping. The study also tries to assess the perceived concerns in online shopping. To know the most popular online site for business in India and the kind of products purchased online shall be the interest of this paper. The association of demographic variables and online shopping shall also be touched upon in this paper. The data shall be collected with the help of a questionnaire administered via random sampling on the rural and urban customer.