Scots pine (Pinus sylvestris L.) is a fast-growing wood that has been widely manufactured into various furnishing products. To improve the machinability of Scots pine, the cutting force and surface roughness during peripheral milling with helical cutters was assessed via an orthogonal experimental design. Experimental results revealed that the resultant cutting force is positively related to the depth of cut, but negatively correlated with inclination angle of cutting edge and cutting speed. However, surface roughness first declines and then increases with increasing inclination angle, and it also shows an increasing trend with the increasing depth of cut and decreasing cutting speed. Furthermore, the depth of cut significantly contributes to the resultant force and surface roughness, while both the cutting speed and inclination angle have insignificant impacts on the resultant force and surface roughness. Finally, the optimized milling parameters were determined as 62° inclination angle of cutting edge, 45 m/min cutting speed, and 0.2 mm depth of cut, and these parameters are proposed for the quality finishing of Scots pine machining.