Sustainable socio-economic development can be looked upon from multiple perspectives, but no longer without considering the roles of urban planning, smart cities and eco-innovative entrepreneurial initiatives. In the context of the COVID-19 crisis, ensuring sustainable socio-economic development is definitely challenging, but not impossible if adopting appropriate measures. This research aimed at analyzing the multidimensional facets of entrepreneurial resilience during times of crisis caused by the COVID-19 pandemic in Romania, while focusing on the effects experienced in the wealthiest areas, specific to urban agglomerations. The research method consisted of constructing a composite indicator comprising appropriate components for assessing the level of wealth and “happiness” of all the Romanian counties. Through the lens of this composite indicator, entrepreneurial resilience was approached in multiple manners according to its diverse forms. Research findings highlight that entrepreneurial resilience tends to be stronger qualitatively and quantitatively in less developed areas than in those that are well developed, mainly due to the lack of entrepreneurial initiatives. Despite being less entrepreneurially resilient, qualitatively, the wealthiest Romanian counties can economically reinvent themselves quicker.