Here's my latest meandering route across the great state of Massachusetts. http://www.gmap-pedometer.com/?r=2011007
I did this one on 6/21 so I had plenty of daylight so no need to hurry.
The start is Newton Corner and the endpoint is the Dreamaway Lodge in Becket. The distance on my cyclometer read- 134.79 the gmaps reads it a little less but doesn't account for elevation change nor was I that specific in marking the waypoints. So let's call it 135 total.
I wish I knew what kind of overall elevation gain the ride had but I'm sure it's substantial. The first 100 is modest with a few challenging climbs after the 50 mile mark but the final 35 miles after Northampton is particularly tough because you've just knocked off 100 miles and then gain a lot of altitude and then lose it in a hurry and have to regain it and more over the last 20 miles- it just doesn't let up. Also the prevailing wind is usually in your face the whole ride.
This route was one of my better ones. It could use improvement going around the Wachusett Reservoir but overall I really like this ride. It would be a nice one to do in reverse with a good tailwind.