In the summer of 2007, Pennington moved to Fairfax, Virginia, to train under Audrey Weisiger. He changed his home club affiliation from the Broadmoor Skating Club to the Washington Skating Club and so competed out of the Eastern Section. Pennington was assigned to the 2007 Finlandia Trophy, where he won the silver medal, placing three points behind Verner and 16 points ahead of bronze medalist Kevin van der Perren. He won the silver medal at the Eastern Sectional Championships to qualify for the 2008 U.S. Championships, where he placed 11th.