Permeable pavements have been used as stormwater management systems throughout Ontario for over 20 years. After years of exposure to sediment and debris buildup surface clogging blocks the infiltration of stormwater and inhibits the hydraulic and environmental functions of the pavement. Removal of surface material has been shown to restore infiltration but practical removal methods have been limited to small-scale testing. This study presents the results and experiences of the first testing of regenerative-air and vacuum-sweeping trucks on permeable pavements in Ontario conducted in 2011. A regenerative-air truck was tested on two parking lots with well-used permeable interlocking concrete pavers and pervious concrete while a vacuum-sweeping truck was demonstrated on a third parking lot with permeable interlocking pavers. Both systems proved to provide partial rehabilitation of the permeable pavements. Post-treatment surface infiltration rates on all three parking lots displayed large spatial variability highlighting that micro-conditions throughout the pavement have a confounding influence over the overall effectiveness of maintenance. The impact of maintenance may be improved by establishing regular cleaning intervals and developing instructional guidelines for pavement owners and equipment operators.