The escalating demand for anthropic needs and urban development has highlighted the importance of monitoring and change detection of land use land cover (LULC). With an increase in agricultural expansion and infrastructural development, every land surface on earth calls for a long-term investigation of land modification patterns and their underlying contributory factors. The present investigation monitors the LULC changes and assesses the process controls in Kohima and Dimapur districts of Nagaland, India. Currently, these two districts encompassing the main urban cities of the hilly state are experiencing rapid urbanization and unplanned developmental activities. Alike any other LULC changes observed in unplanned and developing cities, these districts are likely to face environmental degradation, and particularly, the occurrence of frequent landslides and flash floods. The study has three objectives—(i) LULC mapping of Kohima and Dimapur districts for three periods (1998, 2008, and 2018), (ii) comparative analysis of LULC change patterns in the two districts during the three epochs (1998–2008, 2008–2018, and 1998–2018), and (iii) assessment of the contributory factors. For the study, remotely sensed LANDSAT images (TM and OLI) in Geographical Information System (GIS) platform were utilized along with field surveys. Supervised classification technique was employed and four major LULC classes were identified using Landsat level-1 classification system. The overall accuracy of the classification varied between 91 and 98%. Results showed that Built Up areas have increased significantly in both the districts at the rate of 322.6 ha/year in Kohima and 301.9 ha/year in Dimapur during 1998–2018. On the other hand, Agricultural Land and Forest Land declined in both districts. Changes in LULC were mainly due to marginalization of shifting cultivation, deforestation, infrastructural development, urban migration, and flourishing of aquaculture farming. This study furnishes baseline information on LULC in the data-scarce region of Northeast India and is an insinuation to the policy-makers to ensure sustainable land use planning in the face of rapid urbanization.