Triple-Headed Monster
(64 miles. Three hills combining Greylock, Florida and EHR. Ouch...)
Northampton - Chesterfield - Goshen - Williamsburg Loop (40 miles. Hilly. Notes: A part of Kings Hwy is dirt, so an option is to turn right on Reservoir Rd and left at Northwest Rd. Another option is to go straight on North Rd and turn right on Tob Hill Rd, which merges with Kings Hwy.)