Subwavelength grating waveguide-based micro-ring resonators (SWGMRs) are a promising platform for research in light–matter interaction. However, it is extremely difficult to achieve small radius SWGMR devices (e.g., 5 μm) with satisfying quality factors (e.g., ∼10,000). One major issue is the large bend loss of small radius SWGMRs. In this work, we report the use of trapezoidal silicon pillars instead of conventional rectangular silicon pillars as building blocks of SWGMRs. We found that an asymmetric effective refractive index profile created by trapezoidal silicon pillars can significantly reduce the bend loss and therefore increase the quality factors of SWGMRs. For the first time to the best of our knowledge, we have experimentally demonstrated a 5 μm radius SWGMR made of trapezoidal silicon pillars (T-SWGMR) with an applicable quality factor as high as 11,500, 4.6 times of that (∼2800) offered by a conventional SWGMR made of rectangular silicon pillars, which indicates an 81.4% reduction of the propagation loss. This approach can also be readily employed to enhance SWGMRs with larger radii. We have also experimentally demonstrated a 10 μm radius T-SWGMR with a quality factor as high as 45,000, which indicates a propagation loss as low as 6.07 dB/cm.