We report a wavelength division multiplexed time-bin entangled photon pair source in telecom wavelength using a 10 μm radius Si ring resonator. This compact resonator has two add ports and two drop ports. By pumping one add port by a continuous laser, we demonstrate an efficient generation of two-wavelength division multiplexed time-bin entangled photon pairs in the telecom C-band, which come out of one drop port, and are then split into the signal and idler photons via a wavelength filter. The resonator structure enhances four-wave mixing for pair generation. Moreover, we demonstrate the double-port pumping where two counter propagating pump lights are injected to generate entanglement from the two drop ports simultaneously. We successfully observe the highly entangled outputs from both two drop ports. Surprisingly, the count rate at each drop port is even increased by twice that of the single-port pumping. Possible mechanisms of this observation are discussed. Our technique allows for the efficient use of the Si ring resonator and widens its functionality for variety of applications.