I pedaled out of Kingston this morning just after a hard nighttime rain let up. It let up but never really let go and it was one of those days where there was a light spray in the air at all times. Sometimes it would rain just enough that maybe you’d flip your wipers on if you were in a car, but of course I was on a bike. Luckily it was also rather warm so the ride through the misty spray was border line cool but more or less comfortable.

Out of Kingston the Empire State Trail picked up again and was mostly dirt/ muddy trail. It apparently had stormed hard because there was a number of trees down across the trail. This was proper old rail road tracks converted into trail so it was straight and level. The stickiness of the muddy trail slowed me down a bit but I cruised along without too much effort. My little brother Kyle was taking the train up from Brooklyn to the Poughkeepsie station and I was going to meet him there.

The trail went past a few dark caves that were emitting ice cold air from their depths. I hurried past their icy breath because it gave me the chills instantly. The woods out here were nice. The floor was covered with big orange leafs from last fall and there was occasionally mountain bike trails running through them. It was the first time I thought about mountain biking since leaving Whistler (which was only a couple weeks ago but feels like years ago). I was tempted to stash my pannier bags in the woods and go for a MTB ride on my Weekender but I needed to get to the station. Somewhere in these thoughts I missed a turn and went 4 miles out of my way. Circling back I was now going to be late to meet Kyle and so I pushed hard for Poughkeepsie. 

Crossing the Hudson on the Poughkeepsie rail trail bridge is rad! Extremely tall bridge and only pedestrians and cyclists on it. It’s a good thing to check out even if you just walk to the middle and turn around. Kyle was waiting for me on the other side having just climbed up through a bushy hill of bramble because he couldn’t find the trail. Not for the last time today either. Kyle’s never done any touring or longs rides guessing his longest ever ride was 20 miles (32km). He lives in Brooklyn and gets around by bicycle so I was hoping he’d be better suited for this adventure than he realized. He’s riding a Weekender Archer and didn’t have a rack or a water bottle cage. We tied his backpack to my rack and we started pedaling down the trail. 

This section of the Empire trail was flawless. Paved and wide and pleasant to ride. We cruised along at an easy pace talking. I don’t see Kyle very much and I wasn’t around when he was growing up (him being 14 years younger than me) so there was plenty to learn about him. I was also paying close attention to his riding as I wanted to make sure I didn’t beat him up too badly on his first day. At one point the trail was closed and we were forced to follow a detour. It was a pretty poor detour shooting us out on to some very busy and dangerous roads. Unlike the flat rail trail we were following the roads were upstate NY hilly and challenging for someone who hasn’t been on a bike tour for the last 10 days. Kyle wasn’t enjoying this part but eventually we got around the closed section of trail and were able to join back up with the smooth and flat Empire State trail. 

Finding drinks became and issue at one point and we followed a big sign that said “for drinks and food follow this trail” with a big arrow pointing at a paved trail leading off the Empire trail. The off shoot trail lasted about 25 feet and then just vanished into a gravel covered over grown wasteland. After scrambling along some railroad tracks and crossing a few busy roads we found a gas station across town on our own.

I rode 75 miles (121km) and on Kyle’s first day of touring he managed 45 miles (72km). We ended at a hotel in Brewster, NY. I won’t even mention how harrowing that last mile was getting to the hotel that was off a highway during rush our traffic. Suffice to say Kyle did some more bushwhacking pushing his bike up a big wet tick infested bramblely hill to our hotel rather than staying on that road for one minute more. 

The night’s stop here in Brewster is where the first bikes from my old BMX company T-1 were made by Spooky Bikes. I’ve been to this town before but I weirdly can’t remember much about it. I have vague memories of looking over some drawings with the Spooky team but that’s about it. I wouldn’t want any of the Spooky folks to be offended by my lack of memory, I think it is more a casualty of concussions. I lost a lot of moments from around that time after a few good head bonks. Anyhow, I know this place was crucially important to my life at one point, I don’t remember what happened afterwards though. The bikes that came out of here were legendary that’s for sure!