Another user was able to give me an answer to my dilemma so I probably won't attach a file, but i will provide a bit of an explanation as to what my problem was and the formula provided to me to help correct it in case it may sometime help another.

In my example above I had a formula that would sum all of the "Leave" to "Arrive" times seperately and display them in column C. This was great and to take it one step further I was looking to sum, in column D, the separate durations of only the "1st Street" to "2nd Street".

The formula to sum specific trips (Street 1 to 2,3 to 1, etc) seperately from "Leave" to "arrive",assuming the data starts in A3, is as follows:

=IF(AND(B2="2nd Street", C2="Arrive", INDEX($A$1:$A1,MATCH("z*",$B$1:$B1,1))="1st Street"), SUM(INDEX($B$1:$B1, MATCH("z*", $B$1:$B1, 1)):$B1), "")


Thanks again for the help and hopefully someone else can benefit from this as well.