Low prices have prompted growers to contemplate transitioning to an organic system. We evaluated red clover-maize-soybean-wheat (Cl-M-S-W), maize-soybean (M-S-M-S), and soybean-wheat/red clover-maize-soybean (S-W/Cl-M-S) rotations in organic and conventional systems in New York, USA from 2015 to 2018 to identify profitable organic practices. Organic compared with conventional maize in 2017 had 14.6% higher yield and $2107/ha higher returns above selected costs in the S-W/Cl-M-S rotation; and had $1007/ha higher returns in the M-S-M-S rotation, despite 3.6% lower yield and higher production costs, because of the organic price premium. Likewise, organic compared with conventional soybean had ~$800 to ~$900/ha higher returns in 2017 and 2018, despite ~10% lower yield and ~$50/ha higher production costs, because of the organic price premium. Organic compared with conventional wheat yielded ~4% higher with $125/ha higher returns, despite ~$435/ha higher production costs. Organic compared with the conventional system had $1018/ha higher returns in the Cl-M-S-W rotation, $1782/ha higher in the M-S-M-S rotation, and $2961/ha higher in the S-W/Cl-M-S rotation in 2017 and 2018. Although returns in 2015 and 2016 (no organic premium) were lower, the organic compared with the conventional system from 2015 to 2018 had $673/ha higher returns in the Cl-M-S-W rotation, $497/ha higher in the M-S-M-S rotation, and $2355/ha higher in the S-W/Cl-M-S rotation indicating that the S-W/Cl-M-S rotation was the most profitable organic rotation during the four-year period.