Time series captioning, the task of describing time series in natural language, requires numeric and temporal reasoning, trend interpretation, and contextual understanding. Existing benchmarks, however, often rely on fully synthetic or generic captions, and typically neglect metadata and visual representations. We introduce CaTS-Bench, a comprehensive benchmark for Context-aware Time Series reasoning across 11 diverse domains, centered on a gold-standard evaluation set of 1746 human-rewritten captions that measure how effectively models translate numeric trends into immediately interpretable narratives. To address the scarcity of human-annotated data, we also propose a scalable pipeline for generating high-fidelity synthetic captions, the quality of which we validate. We evaluate leading Vision-Language Models on our benchmark, revealing that even proprietary models struggle to capture numeric nuances in temporal descriptions, while finetuning open-source models on synthetic data yields substantial performance gains. Finally, we release a diagnostic suite of 910 multiple-choice questions and use tailored numeric metrics to gauge time-series-specific reasoning capabilities, establishing CaTS-Bench as a reliable foundation for grounded, multimodal text generation in numeric domains.