What an early start! I've told myself in the past that i'd never do rides that forego sleep but yet here I am. Although I tried to sleep well in the days prior and did get in a good nap earlier in the day and a bit of sleep right before leaving. I decided to leave as early as possible to minimize the headwind's effect on me and to avoid as much rain as possible as a tropical storm drifted north into Boston. I faced an all day east northeast wind while the route trended southeast. Mostly though I was in forest and surrounded by hills so it wasn't too bad. I rode the main roads out of Burlington past the college past lots of students out walking around in groups and enjoying their Friday night. It seemed to take forever to leave the lights and strip malls but soon I was in darkness and out in the Vermont countryside. Very early on I went off course accidentally, down a private driveway. I retraced my tracks and took an alternate grassy path that was minimally used and veered off of my gps track. I went again back to the junction and, it took a second, but I found a singletrack marked with a sign for the Cross Vermont trail. It was a little connector between two back roads, to avoid using the main highway. Soon I rode into the town of Northfield Falls and crossed three covered bridges in quick succession, all in a row. Rolled into town and went a tiny bit out of the way to see another also in town. In adjoining Northfield I rolled by the Darn Tough sock manufacturing facility, and Norwich University, all of this tucked in to a tiny valley, it was very quaint even in the middle of the night. Wish I could have visited during the day. A couple more covered bridges, several super steep climbs and descents, the hours and miles went on and the night got cooler. The temperature bottomed out around 40, and I was warm except my toes were cold. Dawn came and I was very glad because I was also a little bit sleepy but I woke up once the sun came up. It was light enough to see the crossing into New Hampshire, although I was disapointed I didn't get a welcome sign. I made my first stop in a big new Co-op Food Store supermarket in Lebanon and was in good spirits, I was only a little behind my goal time. On track to keep pace for a reasonable ride time. But soon enough I turned off the pavement and was met with a gravel road that said No Outlet. I was sure of my routing and the legality of taking a bike through. But this means one of three things. Either the road is completely closed because it's been gated to all traffic because the other side is now private property. Or there's a bridge damaged or missing where there was one in the past. Or possibly it's open but is unmaintained and is impassable for normal vehicles. It was the latter, which I was not worried about. I had already gone down unmaintained roads earlier in the day, but they didn't last long. This one was over 5 miles long, and it was gnarly. Very very slow going. It was a climb for most of it as well, and while it wasn't that steep, it was very technical with huge rocks everywhere. In a lot of places it was like riding down a creekbed. And then there were all the mudholes. so many of them required careful bypassing on foot on the very edges in the woods. At length I turned on another road, and it too wasn't maintained, another 1.4 miles. All of this required so much extra effort, and while I tried to eat and drink throughout, I was super beaten down mentally and physically. It added a lot of extra time to get through. Thankfully there was a gas station just down the road and even though it wasn't a planned stop, I stopped and grabbed a soda and a snack for my sanity. This helped out a lot and I began to feel a lot better in the miles afterward. It also helped that the terrain was very flat and pretty fast for the next bits. Eventually the hills returned but thankfully all on good fast surfaces. I ended up riding all the way to Manchester before stopping again, at a Market Basket supermarket. I was happy that I made it before the rain, but not long after it began to drizzle lightly. The temps were around 56-60 and so I was still toasty warm just wearing my sunsleeves. I picked up another rail trail in Derry, and followed it down to Salem where I had to do a bit of tricky manuvering around intersections because it wasn't officially laid out yet, but I managed just fine. I stopped at another brand new Market Basket again for soda and insurance food. I didn't want to run out and it also be raining hard. by this point it was still lightly drizzling. I passed TWO more Market Basket stores, both looked open as well, within like a half mile on the same stroad. Crazy. Reminds me of the Ingles situation in tiny Franklin NC. Soon enough though my trail sadly ended and I was dumped unceremoniously onto the streets of Lawrence which was alarming. I tried to make the route through here as much off the beaten path as possible, but this still involved a lot of intersections and there were cars everywhere, speeding all around, turning, zooming around double parked cars and generally doing unsafe things. It was bad enough to be laughable. All this with wet roads too. I kept alert and didn't have any close calls and most of my anxiety was confined to a few areas. Most of it was boring and fine. Further south in the outskirts of Andover, the houses were much wealthier and the roads I picked were pretty quiet. It was actually pretty darn good riding, and this was one of the spots of concern when planning the route since in my experience a built up area this far out from a major city with mostly narrow country roads connecting things tends to be terrible riding. It could just be that it was getting late in the evening and it was raining. Still very light though. The sun was all the way down by this point, as I rode through a lot of very quiet subdivision roads that contained houses that would have been just at home in the Atlanta area. South of I-95 the road network was more grid, and I had a pretty easy time avoiding main roads. I avoided traffic almost entirely until I had to use a bridge over the Mystic and then Charles river. Traffic was not light but I was ok, but definitely getting really tired. Even my right knee was sore from all the effort, something i've never experienced before when cycling. I was very glad to arrive at our place for the night and dry off and get to sleep. I was genuinely worried at various points throughout the ride that I wouldn't be able to finish, even though I really have never had to end a ride because I couldn't do it. And of course in the end this one was no different. But definitely ranks up there with some of the hardest riding i've ever done.