The local running group, Norfolk County Pacers, runs routes starting from the Big Apple, Wrentham, during the fall and it is hilly but quite good scenary to run with.
There are two major loops we use. The ten milers use the short one to start. They should come by the parking lot about the time the 7 milers are ready to go and they can join for the long loop. The 3 milers start last and do the short loop which should put them all on the last approach to the Big Apple about the same time.
This arrangement of overlapping loops can make for a less lonely run.
The short loop:
The long loop:
The Pacers running route page