Hi,
one of my favorite local rides is to head out to Yarmouth. Try coming back down Route 1 sometime when there is a stiff breeze at your back. You won't believe how fast Falmouth shows up. The shoulder is huge and the traffic is usually light. I did that once on during the Yarmouth Clam Festival. The traffic wasn't bad.
Anyway.... Rte 88 to Yarmouth. Head north on Tuttle through Cumberland Center where they decide to call the same road Blanchard or something. Past the Cumberland Fairgrounds is a left that puts you on Blackstrap Road. You can take that back into Portland.
Try Mountain Road sometime, up or down.