We present mid-infrared spectra between 5.2 and 38 µm for 26 disk-bearing members of the ∼5 Myr old Upper Scorpius OB association obtained with the Infrared Spectrograph (IRS) onboard the Spitzer Space Telescope. We find clear evidence for changes in the spectral characteristics of dust emission between the early (B+A) and late-type (K+M) infrared excess stars. The early-type members exhibit featureless continuum excesses that become apparent redward of ∼8 µm. In contrast, 10 and 20 µm silicate features or PAH emission are present in all but one of the late-type excess members of Upper Scorpius. The strength of silicate emission among late-type Upper Scorpius members is spectral type dependent, with the most prominent features being associated with K5-M2 type stars. By fitting the spectral energy distributions (SED) of a representative sample of lowmass stars with accretion disk models, we find that the SEDs are consistent with models having inner disk radii ranging from ∼0.2 to 1.2 AU. Complementary high resolution (R ∼ 33, 000) optical (λλ4800-9200) spectra for the Upper Scorpius excess stars were examined for signatures of gaseous accretion. Of the 35 infrared excess stars identified in Upper Scorpius, only 7 (all late-type) exhibit definitive signatures of accretion. Mass accretion rates (Ṁ ) for these stars were estimated to range from 10 −11 to 10 −8.9 M ⊙ yr −1 . Compared to Class II sources in Taurus-Auriga, the disk population in Upper Scorpius exhibits reduced levels of near and mid-infrared excess emission and an order of magnitude lower mass accretion rates. These results suggest that the disk structure has changed significantly over the 2-4 Myr in age separating these two stellar populations. The ubiquity of depleted inner disks in the Upper Scorpius excess sample implies that such disks are a common evolutionary pathway that persists for some time.