Permeable pavement has been shown to be an effective urban stormwater management tool although much is still unknown about freeze-thaw responses and the implications for deicer reduction in cold weather climates. Temperature data from the subsurface of three permeable pavement types—interlocking concrete pavers (PICP), concrete (PC), and asphalt (PA)—were collected over a seven-year period and evaluated. Temperature profiles of all pavements indicate favorable conditions to allow infiltration during winter rain and melting events, with subsurface temperatures remaining above freezing even when air temperatures were below freezing. Data show that PICP surpassed PC and PA with fewer days below freezing, higher temperatures on melt days, slower freeze and faster thaw times, and less penetration of freezing temperatures at depth.