Indeed, if a is constant, the greater ω is, the greater the maximum speed is.
But when forced to vibrate, a changes with ω. When ω is very close to ω0, the amplitude will become huge. Therefore, on the whole, v is large when vibrating.
Note: There is a formula for college physics:
A 1 is the steady-state amplitude, f0 is the driving force, ω is the driving force frequency, ω0 is the * * * vibration frequency, and β is the damping. It can be seen that when the damping is small, if ω is very close to ω0, the amplitude will be larger.