Fatty acids convert to fatty acid ethanolamides which associate with lipid signalling, fat oxidation, and energy balance; however, the extent to which dietary fatty acids manipulation can impact such control processes through fatty acid ethanolamides-related mechanisms remains understudied. The objective was to examine the impact of diets containing 6% corn oil, high oleic canola oil, docosahexaenoic acid + high oleic canola oil, and fish oil on plasma and organ levels of fatty acid ethanolamides, peroxisome proliferator-activated receptor-α regulatory targets, and lipid metabolism in Syrian Golden hamsters. After 29 days, in plasma, animals that were fed fish oil showed greater (p < 0.05) oleoylethanolamide and lower (p < 0.05) arachidonoylethanolamide and palmitoylethanolamide levels compared with other groups, while animals fed canola oil showed higher (p < 0.05) oleoylethanolamide levels in proximal intestine and liver than groups that were fed coin oil and fish oil. The canola oil group showed elevated (p < 0.01) fat oxidation (%) and over 3.0-fold higher (p < 0.05) hepatic-CD36 expression compared with the corn oil group. Hepatic-lipogenesis was lower (p < 0.05) in hamsters that were fed DHA-canola oil compared with the corn oil group. To conclude, dietary fatty acids produced shifts in plasma and organ levels of arachidonoylethanolamide, oleoylethanolamide, and palmitoylethanolamid, which were accompanied by changes in gene expression, lipogenesis, and energy expenditure, suggesting mechanisms through which dietary fatty acids influence disease risk.