In his hometown of Chappaqua, Sherry ran cross country and track at Horace Greeley High School only in his senior year, having played baseball on a recreational basis up to that point.

[3] While a student at Georgetown, Sherry finished in tenth place overall in the men's race at the 1989 NCAA DI Cross Country Championships.

[3] In a very rare tie, he finished in second place in the men's 5000 meters at the 1991 Summer Universiade in 13:39.31, exactly the same time recorded by Australian competitor David Evans.

[6] In the 2003 Marine Corps Marathon, he almost dropped out in the eighth mile due to a cramp, but felt better en route to win the race.

[8] Sherry currently resides in Great Falls, Virginia, where he runs his sports massage therapy practice out of Commonwealth Chiropractic Center.