The potential airborne transmission of COVID-19 has raised significant concerns regarding the safety of musical activities involving wind instruments. However, currently, there is a lack of systematic study and quantitative information of the aerosol generation during these instruments, which is crucial for offering risk assessment and the corresponding mitigation strategies for the reopening of these activities. Collaborating with 15 musicians from the Minnesota Orchestra, we conduct a systematic study of the aerosol generation from a large variety of wind instruments under different music dynamic levels and articulation patterns. We find that the aerosol concentration from different brass and woodwinds exhibits two orders of magnitude variation. Accordingly, we categorize the instruments into low (tuba), intermediate (bassoon, piccolo, flute, bass clarinet, French horn, and clarinet) and high risk (trumpet, bass trombone, and oboe) levels based on a comparison of their aerosol generation with those from normal breathing and speaking. In addition, we observe that the aerosol generation can be affected by the changing dynamic level, articulation pattern, the normal respiratory behaviors of individuals, and even the usage of some special techniques during the instrument play. However, such effects vary substantially for different types of instrument, depending on specific breathing techniques as well as the tube structure and inlet design of the instrument. Overall, our findings can bring insights into the risk assessment of airborne decrease transmission and the corresponding mitigation strategies for various musical activities involving wind instrument plays, including orchestras, community and worship bands, music classes, etc.