In 1992, at age 30, Elmo, Bruce and I took our first "Old Man Ride", riding two days across Massachusetts from the NY State Line back to Boston. The first half of the trip went great. Then we hit Monson Road.
We still talk about Monson. Gives us the heebie-jeebies. First time since I was a kid when I had to get off the bike and push it up a hill. Walk of shame. Defeated.
To even things up, the Monson climb was stuck 30 miles in to a 69 mile ride. After starting in Sturbridge, I took a "European Vacation" into Holland and Wales (small towns along the CT Border), then positioned myself in Wilbraham to face the climb.
Part of the challenge is psychological -- the first part of the ascent is straight up -- you see the climb, you mentally prepare, you make it to the "top" only to find -- the road turns, you are less than halfway up, and the second half is steeper, hitting 16% grade.
Thankfully, bike and fitness triumphed -- one thing off the bucket list! The remaining 35 miles were still pretty tough, especially when I chose the long, rolling route back through The Brookfields rather than the busy, flat, straight shot on US-20. The one we ignominiously took last time after being beaten by Monson.
Noted after the ride that Strava refers to Monson Road as "The Beast". Beast, dragon -- either way -- slain!