Large bandwidth at mm-wave is crucial for 5G and beyond but the high path loss (PL) requires highly accurate PL prediction for network planning and optimization. Statistical models with slope-intercept fit fall short in capturing large variations seen in urban canyons, whereas ray-tracing, capable of characterizing site-specific features, faces challenges in describing foliage and street clutter and associated reflection/diffraction ray calculation. Machine learning (ML) is promising but faces three key challenges in PL prediction: 1) insufficient measurement data; 2) lack of extrapolation to new streets; 3) overwhelmingly complex features/models. We propose an ML-based urban canyon PL prediction model based on extensive 28 GHz measurements from Manhattan where street clutters are modeled via a LiDAR point cloud dataset and buildings by a mesh-grid building dataset. We extract expert knowledge-driven street clutter features from the point cloud and aggressively compress 3D-building information using convolutional-autoencoder. Using a new street-by-street training and testing procedure to improve generalizability, the proposed model using both clutter and building features achieves a prediction error (RMSE) of $4.8 \pm 1.1$ dB compared to $10.6 \pm 4.4$ dB and $6.5 \pm 2.0$ dB for 3GPP LOS and slope-intercept prediction, respectively, where the standard deviation indicates street-by-street variation. By only using four most influential clutter features, RMSE of $5.5\pm 1.1$ dB is achieved.