Mature wheat kernels contain three main parts: endosperm, bran, and germ. Flour milling results in multiple streams that are chemically different; however, the distribution of antioxidants and phenolic compounds has not been well documented in terms of conventional milling by-product streams. In this study, multiple analytical methods were used to investigate antioxidant activity and phenolic compound compositions of hard red winter wheat (whole ground wheat), the parts of a wheat kernel (bran, flour, germ), and wheat by-product streams (mill feed, red dog, shorts) for the first time. For each mill stream, phenolic compounds (total, flavonoid, and anthocyanin contents) were determined and antioxidant activities were evaluated with 1,1-diphenyl-2-picrylhydrazyl (DPPH) radical-scavenging activity, ferric reducing/antioxidant power (FRAP), and total antioxidant capacity assays. Significant differences (P < 0.05) were observed in phenolic concentrations among fractions of bran, flour, and germ milled from the same kernels and noted that germ accounts for the majority of antioxidant properties, whereas bran contains a substantial portion of phenolic compounds and anthocyanins. Mill feed was high in phenolic content (5.29 mg FAE/g), total antioxidant capacity (866 mg/g), and antioxidant activity (up to 75% DPPH inhibition and 20.26 μmol FeSO4/g). The comprehensive information on distribution of antioxidants and phenolic compounds provides insights for future human consumption of commonly produced co-products from flour milling, and for selecting and using different milling fractions to make foods with improved nutritional properties.