The windy, wet weather didn't stop Cardinal McCloskey Services' first walk-a-thon, Footsteps for Dreams, to benefit the agency and to celebrate its 60th Anniversary. On Saturday, October 28th, 2006, braving a severe morning rainstorm, over 100 supporters of Cardinal McCloskey Services completed the 3 mile walk from Archbishop Stepinac High School past the site of the former Cardinal McCloskey School and Home for Children at Mamaroneck and Ridgeway Avenues in White Plains. DJ Kacey of WHUD's "Mike and Kacey in the Morning" led the walkers as the honorary chairman of this event. Participants included children in Cardinal McCloskey Services' programs, staff members and their own children, board members, and businesses and individuals from the community.

The festivities included a Halloween costume parade and contest, music, face painting, raffle prizes, a moon bounce, popcorn machine, Commerce Bank's "Penny", the coin counting machine, child ID kits, and a birthday cake honoring the agency. Over $40,000 was raised for the agency with iPod's going to the top three fundraisers.