To increase the allowable capacity of wind generation and system reliability of distribution system for islanding operation, an actual Taipower feeder has been selected for computer simulation. The voltage enhancement of distribution feeders with fixed speed wind generator has been obtained by using the static synchronous compensator(STATCOM). The model of Doubly-Fed induction generator(DFIG) in Matlab/Simulink has also been applied in the feasibility study of islanding operation for Taipower feeder. The critical clearing time of fault contingency is solved by considering the low voltage ride through (LVRT) capability of wind generators (WG) and the CBEMA curve of sensitive loads. In this way, feeder circuit breaker(CB) can be tripped in time to achieve islanding operation of distribution feeders without causing the tripping of WG due to voltage disturbance for the system fault contingency. To restore the stable operation of distribution feeders after being isolated from the rest of the power system, an adaptive load shedding scheme has been presented to disconnect the proper amount of system loading to achieve the balance of wind power generation and load demand according to the variations of feeder load profile and wind speed. It is found that system voltage sag problem due to severe fault contingency can be mitigated effectively by using the STATCOM for the support of low voltage ride through capability of WG. With the proper design of protection relay settings for feeder CB tripping and load shedding scheme, the WG and critical loads can be prevented from tripping during transient disturbance to ensure the successful islanding operation of distribution system.