That sounds like fun, Oak.
Just got back from 41.6 miles doing some of my favorite hills in Harvard, MA. I've been out on my bike for 6 weeks and have avoided these hills like the plague, but with my trip to Provence in 6 weeks, I gotta get my azz in gear. Was feeling very anxious about this, and it bugged me until we actually got done with the first climb (Westcott Rd.). My strategy was to maintain a steady slower speed and high cadence all the way up the hill, even when it flattened out. After that, the anxiety was gone, but there were more hills to climb! We ate lunch at the Harvard General Store, and after being 80 degrees and sunny when we arrived, the clouds came. I was thankful, because riding in hot weather, with no transition (it was 70, clear, cool-ish yesterday) gets to me. However, I knew rain was forecast for later in the afternoon, so we headed out, stiff and tired. The first thing was an annoying climb on a busy road, to get to a long downhill. When ever I do this, it reminds me of when your mom tells you not to go swimming after eating! My legs were dead. But, the downhill is nice, and after that, we rode through our old neighborhood, and saw people in our old house, sitting on "our" porch furniture. Creepy.
Anyway, made a couple of "rest" stops between there and home. Ended up with about 1,850 feet of climbing. Need to do a lot more before June 17.