A primary focus of current methods for cluster randomized trials (CRTs) has been for continuous, binary, and count outcomes, with relatively less attention given to right-censored, time-to-event outcomes. In this article, we detail considerations for sample size requirement and statistical inference in CRTs with time-to-event outcomes when the intervention effect parameter is specified through the additive hazards mixed model (AHMM), which includes a frailty term to explicitly account for the dependency between the failure times. First, we discuss improved inference for the treatment effect parameter via bias-corrected sandwich variance estimators and randomization-based test under AHMM, addressing potential small-sample biases in CRTs. Next, we derive a new sample size formula for AHMM analysis of CRTs accommodating both equal and unequal cluster sizes. When the cluster sizes vary, our sample size formula depends on the mean and coefficient of variation of cluster sizes, based on which we articulate the impact of cluster size variation in CRTs with time-to-event outcomes. Furthermore, we obtain the insight that the classical variance inflation factor for CRTs with a non-censored outcome can in fact apply to CRTs with a time-to-event outcome, providing that an appropriate definition of the intraclass correlation coefficient is considered under AHMM. Simulation studies are carried out to illustrate key design and analysis considerations in CRTs with a small to moderate number of clusters. The proposed sample size procedure and analytical methods are further illustrated using the context of the STrategies to Reduce Injuries and Develop Confidence in Elders CRT.