The Thing About Planning

With our train tickets in hand Daegan and I began planing in earnest yesterday.  Our upcoming trip is bookended by two dates: July 22nd on which we board a train in Toronto and ride to Montreal where we spend a night in a hostel in the Plateau, and August 5th where we board a train in in Montreal bound for home. What comes in between is, at the most part nebulous. There will be cycling, no doubt, as that’s how we’ll be getting around. We’ll see a few people I know. There will likely be some swimming, Daegan will take some photographs. We also know, generally speaking, what we won’t be doing. We won’t be bringing camping gear. On our last trip we brought camping gear which we dutifully carried for 2/3 of the trip. We used it one night.  Finally, after hauling this stuff about 330 km (just over 200 miles), we put it in a box weighing 50 lbs and sent it home, traveling that much lighter and faster all the way home and staying in Airbnbs, hostels, and hotels for the last few days of the trip.

Yesterday we had one thing on our agenda: Go to the store and get some more cycling shorts and maybe a few jerseys as well as a new bottle cage, lights for Daegan’s bike (in case we’re out longer than expected) and see how much it might cost to get a solar charger for our phones and speakers.

But we found our way to a rabbit hole: Planning out what comes between the bookends. Where do we want to go? Who do we want to see? How many days of buffer do we want to allow for unexpected stays, weather or mechanical delays and resting? Should we cover lots of ground (100km / 60 miles per day) or allow for shorter and easier days but see less.  We took to Google, creating a shared map.  First we added people we knew we were going to see and put them on one layer of the map. Then we added another layer to the map for things we might want to see: interesting places, landmarks, and of course really good food. Then we went to Only In Your State and scoured there lists for everything from best BBQ to coolest waterfalls to good swimming holes and added them to the list.

We continued putting things on our map and as we went started tweaking potential routes to capture the most things we want to see. Then we’d count the days of riding, then reroute, then add find a link to add more things, then continue.




And we got a lovely map like this:

One of our possible futures

But then we realized that if we were going to get our task done (“You had one job…”), we needed to get out the door and so we packed up our computers, got our shoes on and headed for the store, continuing to make plans as we went.  The conversation went something like “Maybe we could do…” “or…” with nothing really solid coming out of it. Lots of imagining under the guise of “planning our trip” which is very entertaining but later in the day I realized, if you’re doing it to the exclusion of actual tasks (witness our previous morning), you’re doing yourself a disservice. And in the end, the majority of memories from our previous trips have little to do with the things we planned.  The unplanned things were what we still talk about years later.  For example:

In July of 2015 we rode east from Quebec City. We didn’t have much of a plan except a direction: east and maybe to New Brunswick if we felt like it.  A couple of days in we were a bit peckish and there, by the side of the road, was a 70-something year old farmer selling strawberries. We bought a pint and sat with him and ate them right there. His English and my French were about on par so we didn’t say much. We just sat and enjoyed each others company. When we finished we continued east.  A week or so later as we passed going back to Quebec City to catch our train home he saw us and gave us a big wave.

Abandoned Bathroom by Daegan Lunsford on

Last fall we went on a road trip in a rented car. On a spur of the moment decision we stopped at a tourist trap in eastern Ontario. It was amusing enough, but on the way back to the highway we saw what appeared to be an abandoned house. One of Daegan’s favourite photography subjects are abandoned spaces. He spent a good half an hour photographing the space.

In 2012, when Daegan was thirteen, we did our “500 Kindnesses” ride. This epic ride took us from our home in Toronto to Ottawa, Montreal, down through Vermont, New Hampshire, Massachusetts, Connecticut, New York, and even a bit of New Jersey – 1,500 km (about 900 miles) before crossing the George Washington bridge and ending in Central Park.  A ride of this length took a bit of planning just to fit it in to my available vacation and to figure out the logistics of lodging. But even that one had some of the best off-script moments.

It was a hot day. One of the hottest on our trip and by 10:00 AM when we were riding out of Richmond, Vermont, it was in the upper 20’s (close to 90 Fahrenheit). As we rode up a hill, a man in his late 60’s in long pants and long sleeves rode up beside us and started asking about our trip. It turned out he rides nearly every day – about 20 miles or so to stay fit. And even in his outfit he wasn’t even breaking a sweat.  As we rode he told us that if we wanted to cool off we should stop at a somewhat hidden swimming hole. “Just look across the street from the signs for Camel’s Hump”.  Then he slowed down and we rode on, taking his advice.  It was a wonderful break on a very hot day. We stayed there for about an hour, having the place to ourselves and getting “fish pedicures” before they became trendy. Eventually the man showed up and we talked a bit more about his past and the time he’d spent living in Australia.  Soon, though, it was time to move on.

On one of our longest and hilliest days – and that means not only lots of climbs but fortunately descents as well. (Top speed ever for me as a cyclist: 82.5 km/hr (just over 50 mph) on a fully loaded tandem bike!) we eventually found ourselves in Wassaic, NY. As washrooms don’t always present themselves in a timely manner, sometimes one has to find their way in to the woods off the side of the road for a break. On this break we had a surprise. We found ourselves among several beehive-shaped stone mounds covered in ivy. There were signs of people having had camp fires inside (they had smoke holes in the roof) but few other signs of human activity. Not even graffiti which seems ubiquitous in places like this. We had a lot of theories about what they might be but some searching online later provided us the answer: charcoal kilns used to make carbon to create gunpowder around the time of the War of 1812.

Beacon, NY provided us a couple of great moments. In the first, we ran in to a boy of about 8 on his bicycle. He asked us where we were going and we told him: New York City – about 110 km (70 miles) away. He was shocked to find out that a bike could take you that far and even more shocked to hear about how far we’d come. Shock turned to inspiration as he realized he was also straddling such a miraculous means of transportation. “My dad lives in North Carolina. My family could take their car and I could ride my bike there!”  And while it’s easy to dismiss the dreams of an 8 year old, I hope that he remembers the ember of that dream someday and uses it to create his own adventure.

On the other side of town we were on a small residential street where we saw the tableau in the photo above. Deer were grazing just a few feet away from the small street where we stood. After watching for a minute or so we heard the door of the house open next to us. “Look at the deeah,” said the old woman in a strong New York accent. “They come so close to the road, I worry about them.”

And while all of those trips had some planned aspects, I can say that not only was the most magic found in the unplanned moments (and there were many more), in both of the trips I talked about we started with one route and rode a notably different one than we started with.

So at the end of the day I came away with a decision. We’ve got our shared map and it has lots of cool things on it.  We’ve got reservations at a hostel in Montreal and a hotel in Plattsburgh, NY.  But beyond that, we need not make any more plans until we leave. I need to remember that beyond what I’ve already done, reading and “doing research” (particularly about a state I lived in for almost 20 years) is not necessary and is really only a reflection of my excitement and anxiousness to get out there having the unexpected experiences we’ll remember for years to come. Instead I need to do the things I really need to do before leaving – training, shopping, and perhaps most importantly, living my daily life: the one that’s happening today.

And with that,  I will end this. There are potentially interesting Canada Day events happening in our neighbourhood right this minute and I need to get out and enjoy them.

4 thoughts on “The Thing About Planning

  1. I love everything about this except for the idea that you might stop yourselves from spending time doing some really delightful imagining. Yes, you need to do the things on your To Do list. So do them! But there’s nothing wrong with spending a chunk of time dreaming about what might be! That sounds like it was a super fun three hours for you both. Okay. Enough preaching. (Oh, and I’ll be emailing you either today or tomorrow. Gotta catch up on a few things after a busy gig weekend.)

    1. Oh yeah – dreaming is important – it’s how these things get off the ground in the first place. At the same time I have a tendency to read a map like a novel and to turn Google upside down and shake it for HOURS. I think that’s potentially counterproductive. On the other hand, getting a little idea of the route ahead, maybe checking streetview to look for tricky spots or search particularly desolate areas for food stops (or places to refuel just before/after) is really helpful. It’s definitely a balance.

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