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On the map, our planned bicycle trip could be measured in inches: a straight shot up the Hudson River’s narrow blue line, a jaunt along Lake Champlain, a short border crossing into Canada, and voilà – we’d be on international turf. On the ground, however, our more than 370-mile journey from New York City to Montreal took more twists and turns than the map implied.

The good news, I discovered, is that trips like this aren't about fitness – or my father-in-law Dave O’Leary, a former contestant on the epic CBS TV show the Amazing Race, would have left me behind like road kill. They're about persistence and flexibility. And a lot can be said for travelling light.

We brought with us only a handful of modern conveniences: a smart phone, a credit card and a small pack of clothes and rain gear. Easy access to technology gave us the freedom to improvise from some of the tried and true routes found on, which hosts hundreds of maps from people who have done this same trip in hundreds of ways. It also allowed us to make hotel reservations the day of, often just minutes before we pulled into our final stop.

We didn’t always make the right moves; we woefully chose to head up the west side of Lake Champlain, which by consequence included a climb through the Adirondack Mountains. And the hotels we chose weren’t pretty, or always comfortable. But our method meant we could meander at any pace we wanted.

Starting our ride at New York City’s Van Cortlandt Golf Course in the Bronx, a mile of dirt led to the South County Trailway, a 14.1-mile rail trail that stretches from Elmsford, a village just north of the city. Combined with the North County Trailway, the former railway runs for 36 miles of tree-lined near-solitude, away from traffic and – mercifully – from inclines. But it also costs you panoramic views of the river.

Crossing Croton Falls
Crossing the Croton Falls Reservoir on the rail trail. (Grant Burningham)

Gliding through a tunnel of forest, autumn’s leaves had just fallen. Somewhere south of Elmsford, so did we: I glanced back, lost the edge of the pavement and slid end over end, taking my father-in-law with me. We spent our first stop pulling leaves out of our bike shorts. I spent the rest of the five-day trip splinting my broken pinkie finger with duct tape.

Near the town of Carmel, we were spit out into the byways of New York State, just in time for the heat and humidity of hilly Putnam County. Wilting in the autumn swelter, we hit the trip's first real navigation challenge. Instead of relying on my father-in-law’s bike-mounted Garmin GPS, which has a good reputation for getting you where you want to go fast, we spent most of the trip using Google maps bicycling directions, which shouted directions through one of my mobile’s headphones.

The upside is Google takes you on smaller roads, past rustic barns and soybean farms. The downside? It also sent us up at least one endless, winding hill, both of us praying each turn wouldn’t reveal another climb.

A farmhouse outside of Hudson, New York
A farmhouse outside of Hudson, New York. (Grant Burningham)

We were exhausted by the time we arrived in picturesque Rhinebeck, a town of upscale restaurants, historic wooden buildings and the Franklin D Roosevelt Presidential Library. New York City was almost 100 miles behind us, and it showed. Strangers paused to chat, offered us their phone numbers in case we got in trouble and gave us route advice. As we stood in line at a bakery, feeling wrung out and queasy, a man even asked if he could put us up for the night. Despite the temptation, we trekked on.

The next morning’s ride brought our first real views of the Hudson River; with rolling green hills, the hint of the Catskill Mountains, in the distance, we skirted the steep, mansion-lined banks of America’s first great waterway. Yet as we pedalled toward Albany, some 56 miles from Rhinebeck, the sky looked increasingly grim, finally bursting near the city of Troy. The rest of the day was a race against the rain – and not always a successful one.

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