I didn’t sleep well last night. I got less than 5 hours of sleep, waking up at 5 and then unable to fall asleep again; it was probably the nerves before a trip.

I eventually got up, got breakfast, and finished packing for the trip. I left my dad’s house a little after 8 a.m. and headed off down the road.

When I go on a bike trip, I’m fond of taking what I call “new road”—roads I haven’t traveled before. This can mean anything from not taking the same long-distance trip as I have in previous years to making sure that my return route on my regular weekend rides is not the same as the route I went out on.

But today, many of the roads I took in the early miles of the trip were familiar to me, having grown up in that area and known these roads for a long time. Now, granted, in recent years, I’d been far more likely to have driven these roads than biked them, but they were still familiar all the same. In the end, that was a comforting thing.

My route took me right past my old school—Tamarac Elementary, Middle, and High Schools. As I approached the school, I couldn’t help but be reminded of the words of our alma mater—”Mid the rolling hills of Brunswick, with the skies so blue, there stands our honored alma mater, stirring sight to view”— as I rolled past those same rolling hills of Brunswick. And to be sure, that song got stuck in my head for a good hour or more until I  was well out of Brunswick and Willie Nelson’s “On the Road Again” took over.

As I rode past my old stamping grounds along Tamarac Road, I went past side roads, many of which bore the names of people I knew, people I went to school with: Lockrow, Herrington, Snyder, Eddy, Cushman, Delamater. It was like being seen off by old friends.

Eventually, Tamarac Road merged with NY Route 7 and that became my way east toward Bennington, Vermont. I was making really good time, averaging about 15 miles an hour and feeling strong. I had noticed right when I set out that the hills didn’t seem to be as much of a problem as they had been on previous trips. Even with the bike weighing an extra twenty pound because of my panniers, the going felt relatively easy. Then it occurred to me: I weigh a good 20 pounds less than the last time I did a trip like this. Not having to push that weight up these hills was a nice benefit.

After 37 miles, I crossed the border into Vermont and went through Bennington. Bennington is a lovely town but I wasn’t staying long. With such a long day planned, I wanted to get much further down the road before stopping for any appreciable break. And so after getting a shot of the Bennington Monument in the distance, I continued on my way north out of town.

It was here that the terrain began to change. There were longer and steeper inclines and the road surfaces weren’t always ideal. At one point, the road surface turned into a kind of packed gravel. The going was getting difficult and I began to wonder whether I was at long last running out of energy. But eventually I crested the hill and began a long descent that gave my legs a chance to rest. And thus it occurred to me that the reason I was tired was that I had been climbing a fairly serious incline for a while. (You can see it at the 49 mile mark on the elevation chart below.)

At the bottom of the hill was a little boy selling lemonade. I pulled right up and bought a glass, which I downed right away. Continuing along, I came to the town of Arlington, Vermont, in which a Norman Rockwell festival was going on. It looked like fun, but I wanted to press on. Nine miles away was the town of Manchester and that was my intended lunch destination.

When I first set out on these trips in 2010, I made a lot of mistakes in how to approach the riding. That first day, I stopped after 38 miles in Baltimore (out of a total of 87 for the day) and had a quick snack in the inner harbor before moving on. I learned two things that day: (1) it’s rough to interrupt your momentum—it’s a lot harder getting your legs moving again once you’ve stopped; and (2) if you’re going to stop, stop for a while.

What seems to work for me is to stop no sooner than 2/3 of the way to the end, and on a day on which I needed to travel 96 miles, that was going to need to be around 64 miles: i.e., Manchester. And so, I pressed on. When I got to Manchester, it was definitely time to stop. My legs were organizing a revolt and demanding better working conditions. I got to Manchester, headed through the main part of town and found a Stewart’s Shop along the way.

Anyone who’s lived in Upstate New York or Western New England knows Stewart’s. They are the reason that 7-Eleven has never made any inroads in the region and we feel about Stewart’s the way that folks in the Philadelphia area feel about WaWa. I stopped, had lunch, charged my phone, and sat. I was determined not to leave before I was ready. I was looking at my calorie tracking app with some amusement—it was telling me I had a 4,000 calorie deficit to work with. And I ate. And I had a Stewart’s chocolate milkshake (if you’re from the region, you’ll understand). After eating, I bought some water to refill my water bottles and another bottle of Gatorade. I went outside and sat on a bench next to where I’d parked my bike. While sitting there and resting, I had a number of nice conversations with some friendly Vermonters—a mom, dad, and kid getting ice cream; and two older men, out riding their motorcycles. We talked about my trip and folks they knew who were doing similar things. And before long, an hour had passed. My legs were feeling rested and the carbs from the milkshake were doing their thing, so it was time to move on.

At this point, I only had 32 miles to go and the going was not difficult. There were still some inclines but they tended to be gradual. I was traveling north on US 7 and the grade that such roads tend to take is never terribly steep. The bigger problem was the heat, though, with years of experience biking in D.C., even that wasn’t too big of a problem.

But, once you stop, it’s never quite the same when you start up again and the heat of the day and the many miles to go were taking their toll. Each mile seemed to take just a little longer than it should. Not even the gorgeous scenery could make the miles go by faster.

Now, you may be wondering why it was that I was traveling such a long way on this first day. There were a couple of reasons. I like to travel an average of 75 miles a day. At 75 miles on this leg, however, there was nowhere to stay. I was faced with the choice either of falling behind on my first day by stopping after only 60 miles in Manchester or pressing on to Rutland. Given that it was the first day and my legs would be fresher, I decided to press on.

Eventually, I got to Rutland, a little after 5 p.m. My hotel is comfortable, has a whirlpool hot tub in the pool area (perfect for soaking my sore legs), and is right next to a steakhouse. Around mile 70, I started fantasizing about the dinner I was going to have and knowing that carbs are good in the morning and protein better in the evening, I had been wondering whether a steak was in the offing. And it was. And it turned out that the couple sitting next to me were Russian and I got to practice my Russian a little bit with them over dinner.

Back in the room, I’m thinking about what I was able to do today. I got within 2-1/2 miles of biking a century. (No, I was not at all tempted to ride around for a couple of miles to actually get one—I’ll have a chance to do that later on.) After a four year hiatus from these long distance bike rides, I was in fact able to get back in the saddle and to make substantial progress on my first day.

So, now, with this sense of satisfaction, the order of the evening is to relax a little, watch the rest of the Red Sox-Yankees game on TV, take my ibuprofen, and get some sleep.

I don’t think I’ll have trouble sleeping through the night tonight.

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