The Eastern Uttar Pradesh (UP), comprising 28 districts, is officially designated as the most backward region in Uttar Pradesh and each district faces situational factors of development which are unique to it. Using a household survey conducted on 560 households in Balrampur, Shrawasti, Bahraich, and Siddharthnagar, this paper aims to understand the dynamics of backwardness in the aspirational districts of the Eastern UP. The study employs Gini coefficient, Lorenz curve, and MPI (based on Alkire and Foster (2010) methodology) to understand the nature and causes of income inequality and multi-dimensional poverty. The factors, which affect MPI, have been identified with the help of multiple tobit regression analysis. The findings reveal the presence of significant income inequalities among districts, social groups, and areas of residence. Multi-dimensionally poor were the highest in Shrawasti (61.5%) followed by Balrampur (54.5%), Bahraich (37.6%), and Siddharth Nagar (34.9%). Regression results show that area of residence, region, caste, education level of the family head, income of the household, and out-of-pocket health expenditure, are the statistically significant determinants of the MPI. The paper suggests that the policy makers should first enhance the income levels of the household and then remove high income inequality. Providing urban amenities, education, ensuring a regular source of income along with cost effective and timely availability of healthcare services can prove more effective in reducing backwardness and making them 'Aspirational' in the real sense.