I'm thinking something like this for tomorrow:
https://ridewithgps.com/routes/30923335. Familiar roads to Williamsburg center, then some scenic climbing through Worthington and Cummington, possibly with a stop at the Old Creamery; more scenic climbing up Spruce Corner Rd to Ashfield, then back via 112 and a screaming descent on Rt 9. Somewhere between 50 and 55 miles, probably, and about around 3000' of climbing.