The evaluation of satellite soil moisture is a big challenge owing to the large spatial mismatch between pixel-based satellite soil moisture products and point-based in situ measurements. Upscaling in situ measurements to obtain the “true value” of soil moisture content at the satellite grid/footprint scale can make up for the scale difference and improve the validation. Many existing upscaling methods have strict requirements regarding the spatial distribution and quantity of soil moisture sensors. However, in reality, soil-moisture-monitoring networks are commonly sparse with low sensor density, which increases the difficulty of obtaining accurate upscaled soil moisture data and limits the validation of satellite products. For this reason, this paper proposes a scheme to upscale in situ measurements using five machine learning methods along with Landsat 8 datasets and DEM data to validate the accuracy of a SMAP-enhanced passive soil moisture product for a sparse network on the Qinghai–Tibet Plateau. The proposed scheme realizes the upscaling of in situ soil moisture data to the pixel scale (30 m × 30 m) and then to the coarse grid scale (9 km × 9 km) by using multi-source remote sensing data as the bridge of scale conversion. The long-time SMAP SM products since April 2015 on the Qinghai–Tibet Plateau were validated based on upscaled soil moisture data. The results show that (1) random forest regression performs the best, and the upscaled soil moisture data reflect the region-average soil moisture conditions that can be used for evaluating SMAP data; (2) the SMAP product meets its scientific measurement requirements; and (3) the SMAP product generally underestimates the soil moisture in the study area.