This route is flat to rolling for the first 40 miles with only a couple of small hills. The last 30 miles includes three moderate climbs of 300-400 vertical feet, but none are steep. The intended food stop at Wassaic, mile 40 appears closed. The route's total distance is a modest 69 miles, with 4500 total vertical feet of climbing.
Note return trains run every other hour from Pawling. Please check current train schedules on the Harlem line. Don't forget your Metro North rail pass! Route is never too far from train stations if bailout is needed. There are sections of hard pack roads.
Consider dining in Pawling post ride.