DNF. It was going SO well until it wasn’t. 😢 Melinda wasn’t feeling as good as the week before but spirits were still high. Both of us had been looking forward to our new tradition of doing a double century for the summer solstice. I was really stoked about the route I had come up with and we were more prepared than last year. I bought a tri-style dual bottle cage seat mount so I could hold a couple storage bottles. One for my repair kit and the other to store a sandwich (wrap) and the layers I was going to take off later. My bar bag was filled with Skratch, batteries (too many) and some more snacks. Like so many rides, it started off with indecision about what to wear and how much to bring. Storage was at a premium as I brought, in hindsight, way more than I needed so I decided not to bring a vest and just go with the light jacket. I definitely wasn't going to wear a base layer as it was going to be hot later in the day. At first, it felt like the jacket had been a mistake and a vest would've been better but once we got on Canada it got colder. As we got further into the ride it got colder still, especially in Woodside and La Honda. There were parts of the ride where the sun was really warm but the wind chill was even colder, especially along the coast. So while the jacket was helping, it wasn't enough sometimes (but also too much other times). The wind was this biggest concern for the day, particularly the headwinds coming back. The thing we didn't expect was how cold the wind would be. We climbed OLH right around sunrise, which was pretty through the trees and got to enjoy a moody vista on WOLH. Lots of wild life about, with a bunny sprinting across the road in front of me as I was going around a high speed corner during my descent. We rolled into Pescadero on time and stopped to try and have a snack but everything hadn't opened yet. I expected to see the Pescadero Road Race staging but I guess it was staging somewhere else because it was a ghost town. I had room to bring half a Turkey Cranberry Wrap which I ate. Melinda brought up tryptophan causing sleepiness which, honestly, I never thought about except for Thanksgiving turkey, and has never been a concern. We had near perfect conditions for the coast. It was sunny and clear, with just a bit of haze. The ocean was a beautiful turquoise. And we had some glorious tailwinds. Melinda was getting hungry so we briefly backtracked to go to Swanton Berry Farm and found out just how glorious the tailwind was. Right in our face! Unfortunately, they didn't have anything she wanted so we rolled to Davenport, which luckily isn't far away. We stopped at Whale City Bakery for food. We grabbed a table outside and while we were waiting to order, a guy came over to us and asked us if we had seen his backpack. He said it had all his stuff in it. He pointed over to his bike laden with bikepacking bags. I was facing the direction of his bike and hadn't noticed his backpack but also didn't see anyone go by his bike. It seemed so unlikely that anyone (in the area) would be taking a random bag. We mentioned it to the waitress and she felt the same. I could see him retrace his steps. As we were ordering, I saw him come back and wait nearby. After we ordered, he let us know that he had forgotten his bag over at the store across the street. The croissant sandwich I ordered was not great. I like my eggs and bacon cooked a certain way and how they made it was not that way. To be fair, I think it's the standard, no frills, just cook them plain way. I ate it to eat it. Even the croissant wasn't that great. It all just tasted greasy and weirdly on the sweet side instead of being salty or savory. We rolled through Santa Cruz, which wasn’t as busy as I expected it to be. We stopped for some Ice cream at The Penny Ice Creamery in which Melinda declared the mint in her Mint Chip ice cream to be “too planty”. She could taste the leaf of the mint. My original route was just shy of 12K of elevation so to get it there, I added Cox Rd., a spur of Day Valley Rd. that we ride all the time. Being a spur, it’s less used and far prettier but it also adds climbing and miles which is why we’ve never ridden it before. I’d consider riding it again. Melinda was sleepy from the start. When we got on to Hames Rd. she mentioned how, “if there was a mattress, I would fall asleep on it right away.” Then we turned the corner and there was mattress (that looked like it was in pretty good condition for a “road mattress”) sitting in the shoulder ahead of us. :) We stopped off at Corralitos for a snack and some Gatorade. We were behind schedule but we also had more front loaded climbing this year than last year. And the back half this year had less climbing and was mostly flat so we were optimistic that we were still on schedule. The only concerns being, not knowing how bad the headwind was going to be and Melinda’s knee was bugging her. Bob and Sonny were also in the area doing parts of the same route as us. We were hoping to meet them and to get a tow in the headwind from them but they were behind us. I told them to catch us on the climb up Eureka Canyon. On the climb, the Gatorade kicked in for Melinda and we were setting a pretty good pace up it. The headwinds on Summit (and the rest of the ride) ended up being way less than expected which we were very happy about. We felt better about finishing on time. We decided to stop at the Summit Store for some water and another snack. I think it was when I was in the store that we missed Bob and Sonny go by. Too bad. The descent down Old Santa Cruz Hwy was fun but at the bottom of it, Melinda got a rear flat. This, unfortunately, was the beginning of the end. After we got going again, I had an issue with my new bottle cage mounts. I’d been sort of having an issue all day anyway where the repair bottle kept popping up, in danger of flying out of the cage. On Los Gatos Creek Trail, Melinda yelled out that my bottle was coming out. Luckily she was behind me. I stopped but it already fell out because the top screw mounting the bottle cage had come undone and the cage swung down. Luckily she found the screw and I was able to put it all back together. Once we got to the end of the trail, I saw that the screw was halfway loose again. Turns out, the screws for both cages had gotten loose from all the shaking. I guess I should’ve used Loctite on them. I tightened them down again and they were okay for the rest of the ride. At that point we had spent so much time with mechanicals, finishing the whole route at a reasonable time didn’t seem possible. We decided to cut out the loop down to Morgan Hill and just cut across San Jose to catch Coyote Creek Trail further along the planned route. We figured if we had the legs and the time, we could add those miles back in at the end, closer to home. It also had the benefit of being able to get more layers as it was getting cold. This was at mile 120. We found a Popeye’s en route, which turned out to be the same Popeye’s we had gone to before after doing Calero County. Over dinner we contemplated just going straight home or calling a Lyft. We saw it was ~35-40 miles to ride more directly home and figured that was doable so we felt good about riding that. Unfortunately when we got started, Melinda’s knee was hurting pretty badly. On any sort of climb, she was really just pedaling with one leg. Hoping it was going to get better but seeing the pain on her face that it wasn’t, when we were passing Tamien Caltrain station, I called it. We figured out Lyft was going to be way more than Caltrain so we took that instead. There were more fails and shenanigans to come. We got on the platform and saw a train leaving in our direction. We were bummed about that but saw that the next train was leaving pretty soon. This was my first time riding Caltrain and I have to say their signage needs a lot of work. While we were sitting waiting for the train, the train that had been on the track behind us started to leave. It ALSO was going in the direction we wanted. We look up at the sign to see it was the 9:05p train we were expecting to catch that was departing. My heart sank because the next train, according to the sign, was 11:05p. We couldn’t believe it. The whole time the train had been sitting there, the doors were closed so we assumed it was out of order and because it was on the other track, also assumed it was headed in the other direction. It was pretty cold and I didn’t want to wait two hours for the next train. Our options were limited though. Melinda looked up the schedule and saw there was a train leaving from San Jose Diridon at 10:19p. It was only a few miles away so we rode over to catch it. The bike trail after dark didn’t seem like the best idea. Lot’s of broken bottles, it’s overgrown and plenty of homeless camps too. Coming around one corner, we see a guy with a bike standing in the middle of the path with what looks like a dog. As we got closer, he moved to one side. His dog didn’t move only it wasn’t a dog. It was a baby skunk! We rode right between them. The path wasn’t that wide and luckily the skunk didn’t feel like spraying us. That would’ve just really been the icing on the cake for our evening. We got to the station with plenty of time and more awareness of which train we had to catch and where. Caltrain really needs to improve their signage and make it clear where to go. There was a train sitting on the track we were expecting to take but the doors weren’t open. We had to assume it was the right one. The doors eventually opened as the departure time neared and we got going. As we rolled into the Menlo Park station, I got to see the lot where Off The Grid is held and where we get blasted by the train horn all the time from the train’s perspective. We got back to Belmont and tried to figure out the best place for Melinda to wait while I rode home to get the car so I could drive her back. She was barely able to walk up and down the stairs at the Caltrain. Nothing was really open except the gas station so we decided to meet there. Turns out Chuck’s Donuts behind the gas station was open. Even better. I TT’d it home as fast as I could and was pretty happy with my legs all things considered. I even got so warm I was sweating again. We were both disappointed we didn’t get to finish it but at least we didn’t have to end the ride because of anything worse. And we get to redo this route another time and saw all the pretty sites all over again. One potential change would be the bike paths through San Jose. While we believe we would’ve been through them before dark, it’s something we wouldn’t want to do if it’s dark.