Middletown to Putnam is 51.8 miles out and 51.8 miles back for a total of 103.6.
Click the link below to see the route on Ride with GPS

Ludlow to Woodstock is 26.8 miles 3 gravel sections and Woodstock back to Ludlow 4 more gravel sections in the last 35.2 miles
for a total of 62 miles

73 miles of epic and very challenging off-road riding including 9,000 feet of climbing. The VT Monster is best attacked with a Cyclocross bike though Road, Mountain can handle it.