The gradual decline in routine patterns is a major symptom of early-stage dementia, therefore an unobtrusive real-life assessment of the elder's routine can potentially be of significant clinical importance. This article focuses on the assessment of changes in a person's daily routine using longitudinal data recorded from a network of nonintrusive motion sensors in a smart home environment. In this article, we propose to identify repeating patterns in a person's daily routine over the span of multiple days using hierarchical clustering algorithms, which provide an effective way to mitigate noise artifacts and confounding factors that contribute to the momentary variability of the sensor data. We have evaluated our proposed algorithm on both synthetic and real-world data recorded in the span of 50-100 days from four elderly adults. Our results indicate that the proposed hierarchical clustering approach can more reliably capture the gradual change in the degree of routineness compared to baseline approaches that measure the similarity between two consecutive days or capture variations in the occurrence of recognized activities.