Oolong tea presents notable variations in taste profile and aroma characteristics under different cultivation conditions, particularly across altitudes. However, systematic investigations into the altitude-induced differences in key taste compounds and aroma composition remain limited. In this study, we examined six oolong tea cultivars, comparing their taste-related chemical constituents and aroma profiles under high- and low-altitude cultivation. Sensory evaluation, high-performance liquid chromatography (HPLC) and headspace solid-phase microextraction-gas chromatography-mass spectrometry (HS-SPME-GC-MS) were employed to characterize these differences. Sensory evaluation revealed that high-altitude oolong teas exhibited enhanced umami, sweetness, and floral intensity. In most cultivars, the levels of free amino acids, polyphenols, and soluble sugar were relatively higher under high-altitude conditions. HS-SPME-GC-MS identified 55 common volatile organic compounds (VOCs), with terpenes and esters comprising the largest number of compounds. Identification by partial least squares discriminant analysis (PLS-DA) combined with relative odor activity value (rOAV) screening yielded 22 candidate differential volatile organic compounds. Floral monoterpenes, including linalool, linalool oxide II and geraniol, were consistently higher in high-altitude teas, whereas most other volatiles varied primarily with cultivar rather than altitude. These chemical patterns are consistent with the sensory finding of stronger floral intensity in high-altitude samples. This study provides theoretical insights for cultivar selection and quality improvement of oolong tea grown in high-altitude regions.