We present detailed modeling of the spatial distributions of gas and dust in 57 circumstellar disks in the Upper Scorpius OB Association observed with ALMA at submillimeter wavelengths. We fit power-law models to the dust surface density and CO J = 3–2 surface brightness to measure the radial extent of dust and gas in these disks. We found that these disks are extremely compact: the 25 highest signal-to-noise disks have a median dust outer radius of 21 au, assuming an R−1 dust surface density profile. Our lack of CO detections in the majority of our sample is consistent with these small disk sizes assuming the dust and CO share the same spatial distribution. Of seven disks in our sample with well-constrained dust and CO radii, four appear to be more extended in CO, although this may simply be due to the higher optical depth of the CO. Comparison of the Upper Sco results with recent analyses of disks in Taurus, Ophiuchus, and Lupus suggests that the dust disks in Upper Sco may be approximately three times smaller in size than their younger counterparts, although we caution that a more uniform analysis of the data across all regions is needed. We discuss the implications of these results for disk evolution.