Distance: 40 / 67 miles
Climbing: 65 / 65 feet per mile

​Description: This ride is a combination of the Madison–Greene and the Madison–Orange rides, covering a large section of southern Madison County and part of northern Greene County. It includes a moderate, fairly steep climb up Little Skyline Drive outside of Orange for some exceptional views.

Stores: Mile 21 (Orange); mile 35 (Somerset; long route); mile 59 (long route)

Alerts:
1. Both routes cross US 29 at the beginning of the ride; the long route crosses it again at mile 44. Use caution.