The flavor of fresh, raw milk is considered to be the key to maintaining the quality of dairy products, and is very crucial in affecting a consumer’s choice. To better understand the differences in flavor of fresh milk between feeding patterns, we conducted the following study. Twelve Holstein cows reared in pure grazing mode and twelve reared intensively in medium to large farms were selected from the Xinjiang Uygur Autonomous Regions at the same time, and the flavor of their raw milk was analyzed. Aroma profiles and taste attributes were assessed by electronic nose and electronic tongue, respectively, and volatile flavor compounds were characterized and quantified by Headspace-Solid Phase Microextraction/Gas Chromatography-Mass Spectrometry. Thirteen volatile compounds were identified in the indoor feeding pattern and 12 in the grazing; most of them overlapped. W1S, W2S and W5S were the main contributing sensors of the electronic nose for the overall assessment of the aroma profile. Raw milk from grazing had more intense astringency, bitterness, sourness and richness in taste compared to indoor feeding. Different dietary conditions may contribute to a variety of aroma profiles. Oxime-, methoxy-phenyl-, octadecanoic acid, furfural and dodecanoic acid were the key volatile flavor compounds of grazing. Meanwhile, raw milk from indoor feeding patterns was unique in 2-nonanone, heptanoic acid and n-decanoic acid. All three detection techniques were valid and feasible for differentiating raw milk in both feeding patterns, and the compounds were significantly correlated with the key sensors by correlation analysis. This study is promising for the future use of metabolic sources of volatile organic compounds to track and monitor animal feeding systems.