Thanks to all for the replies.
Machka, hard to avoid climbing here. It's about 3,000 meters in the 100 miles. Sound advice on the crossing of traffic.
Skiffrun, I see you did some research:-). You'ld be surprised at how rural Rockland county is. We plan to do the first run as club rides with one or two leaders per group.
BrazingHot, They chipsealed most of the roads this year so we should be good but thats a valid point and has be suffered by some ride leaders this year.
clasher, great suggestion on the heat maps.
Thanks again.