The school education sector is one of the severely affected sectors due to COVID-19 pandemic. In India, the education sector is one of the severely affected sectors due to this pandemic, especially the regional language schools as 83% of Indian school students study in regional language schools. The impact on education sector may not be visible immediately, however it will have long term repercussions on the quality of education thereby on the future workforce as well. Globally 1.1 billion children and 430 million children in India have been affected since schools have been closed due to this pandemic. Though the private sector and higher education institutes have transitioned to the online teaching mode to cater to the needs of the students, but the challenges for adapting the online teaching by regional language schools are immense and mammoth. The objective of this study is to identify the needs and challenges for adapting the readiness of such schools in Maharashtra - the most economically developed state in India. The pilot study has revealed some startling results like lack of regional language content, insufficient training to online teaching tools and unavailability of IT infrastructure resources causing major issues to conduct online lectures. However there is a need for comprehensive survey to study the issues in the digital transformation of regional language schools. Keywords:COVID-19, Digital Transformation, Regional Language Schools, Online Learning, India, Maharashtra, School Education