The viscoelastic glass-to-rubber softening transition is analyzed for various cross-linked polymers reinforced with filler particles. We find that the loss modulus peak corresponding to the segmental relaxation process (glass transition) is not significantly affected by the particle surface area in carbon black-filled polybutadiene or by silane chemical coupling of poly(styrene-co-butadiene) to silica. Large differences in shape and magnitude of the peak in the loss tangent (tan δ) vs temperature are noted for these materials; however, this is due to variations in the storage modulus at small strains in the rubbery state, which is influenced by the nature of the jammed filler network. The use of a simple relaxation model demonstrates this feature of the viscoelastic glass transition in filled rubber. It is not necessary to invoke concepts involving a mobility-restricted polymer layer near the filler surfaces to explain the viscoelastic results. Atomic force microscopy conducted with an ultrasharp tungsten tip indicates that there may be some stiffening of the elastomer in the proximity of filler particles, but this does not translate into an appreciable effect on the segmental dynamics in these materials.