I've filled in a few more "historic" trips from the 90s and oughts, plus I recently got back from a long weekend trip from the FedroSplat to Connecticut and back. Drove the clinching pieces of PA194 and NJ53 on the way up, as well as driving all of NY304, though that last was not intentional; I'd intended to take the PIP north of the Thruway but it was blocked due to downed trees in a couple of spots after the recent storms. So I ended up driving the north half of NY304 and a new-to-me segment of US9W (with part of the latter also being a new-to-me segment of US202). Also extended my mileage on NY301 before passing into CT.
In CT and on the return trip, I drive new segments of quite a few CT routes, US5, and US44, but only one newly clinched route (CT194), and a piece of NY303. I did add a couple of weirdnesses due to that storm though. CT37 does *not* have a waypoint at Haviland Hollow Rd (though the other end of that road *is* a waypoint on NY22), so after driving north from that road up to New Milford on a past trip, I had listed my south end as Beaver Bog Rd, the closest waypoint, about 3/4 mile south. So on this most recent trip I planned to drive CT37 from I-84 north to Haviland Hollow Rd. I made it north of Beaver Bog Rd, but about 3/8 mile short of my intended turn I hit a "Road Closed" sign, and highway workers telling me that CT37 was impassable due to downed trees and poiwer lines. I was directed onto a side road, which was barely passable (only one car wide in a lot of spots after they'd cut parts of the downed trees out of the way), and the other end of which was at a road I later determined was CT39... but I had no data signal and ended up making a wrong turn, went east, and found myself 1/2 mile west of CT37 before turning around and going back west toward NYS. I did eventually make it to my destination, but now I have a couple of ALMOST-clinched segments up in CT that I'll have to finish doing the next time I'm solo driving up that way.