The purpose of this study was to investigate the effects of pasture versus indoor total mixed ration (TMR) feeding systems on the chemical composition, quality characteristics and sensory properties of full fat Cheddar cheeses. Fifty-four multiparous and primiparous Friesian cows were divided into 3 groups (n = 18) for an entire lactation. Group 1 was housed indoors and fed a TMR diet of grass silage, maize silage and concentrates, Group 2 was maintained outdoors on perennial ryegrass only pasture (GRS), while Group 3 was also maintained outdoors on perennial ryegrass/white clover pasture (CLV). Full fat Cheddar cheeses were manufactured in triplicate at pilot scale, from each feeding system in September and were analyzed over a 270 d ripening period at 8°C for chemical composition, textural characteristics, sensory and volatile properties. Pasture derived feeding systems were shown to produce Cheddar cheeses more yellow in color than that of TMR, which was positively correlated with increased cheese β-carotene content. Feeding system had a significant effect on the fatty acid composition of the cheeses. The nutritional composition of Cheddar cheese was improved through pasture based feeding systems with significantly lower thrombogenicity index scores and a greater than 2-fold increase in the concentration of vaccenic acid and the bioactive conjugated linoleic acid c9t11, while TMR derived cheeses had significantly higher palmitic acid content. Such alterations in the fatty acid profile of the cheeses resulted in pasture derived cheeses having reduced hardness scores at room temperature. Feeding system and ripening time had a significant effect on the volatile profile of the Cheddar cheeses. Pasture derived cheeses cheese had significantly higher concentrations of the hydrocarbon toluene. Ripening period resulted in acids, alcohols, aldehydes and ester based compounds. Fatty acid profiling of cheeses coupled with multivariate analysis showed clear separation of Cheddar cheeses derived from pasture-based diets (perennial ryegrass or perennial ryegrass/white clover) from that of a TMR system.