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Bicycling from Boston to Wisconsin

My first bike.

My first bike.

Starting Out

When I was 22 years old, living in Boston, I decided to ride my 10-speed bicycle to Wisconsin.

I bought front and rear panniers for cargo space and dried camping food for sustenance. For shelter, I purchased a waterproof nylon poncho for above, a vinyl tarp for below and a sleeping bag.

I trained, riding about ten miles a day for a short three weeks, and felt I was ready to go.

Boston to Southern Connecticut

The first day I headed out across the Massachusetts Avenue bridge over to Cambridge and continued north to Route 16 west, and continued through the suburbs in a southeasterly direction until I got to Douglas State Forest near the Connecticut border, where I planned to camp. The first day was about a sixty mile ride.

Douglas State Forest had no campground, so I rode down a logging road until I was out of sight of all houses and erected my poncho. Naturally it rained. Since it was my first night sleeping under the poncho, I didn't know any better, so I set it up too flat. The rain collected on one end and then splashed over onto my feet all night. Also I did not know that a lot of Douglas State Forest is wetland, and I did not bring any insect repellent. I spent a miserable first night with my sleeping bag wrapped tight around my head as the mosquitoes attacked my forehead and scalp.

The next day, while my sleeping bag was in the dryer at a local laundromat, I went out and bought some insect repellent with extra Deet. Carcenogenic? Smarcenogenic! I didn't care. I just was not going to have another night like that.

When my sleeping bag was dry I headed down highway 12, over the Connecticut hills to the New London area. There I spent two nights resting and deciding whether to continue or give up and go back to Boston.

Bikes in repose.

Bikes in repose.

Out of Connecticut

My next stop was Brewster, New York, about a hundred miles away. I headed west, but shortly I ran into trouble when one of the spokes on my back wheel broke. As I was wheeling my bike along a country road, wondering how I was going to make the fifty miles to my destination campground that night, a woman saw my plight and said her son was pretty handy and could maybe help me out. He was about nine years old, but sure enough, he got that bike ridable. It had kind of a hop, but I managed to limp into a bike shop at North Haven, Connecticut. There I had to spend about half my cash on a new wheel and an extra handlebar bag, which I piggybacked on the front of my other handlebar bag to take some weight off that back wheel.

By the time I got out of the bike shop it was almost dark. I had no lights and would have had a hard time navigating in the dark, so I just pulled off into a wooded lot not far from a house, rolled my sleeping bag in the vinyl tarp and hoped for the best. Luckily it did not rain and no one called the police and I had a reasonably restful night.

The next day I passed into New York, where I bought a New York State road map.


Almost Bike-Jacked

After I figured out where I was on the map I plotted a course westward to my next stop. The roads were rolling and the weather was good.

When I was about three quarters the way there, two boys maybe eighteen years old in a car pulled off the road just ahead of me. I stopped and they got out of the car.

"Let's have a talk," one of them said, and one of them got on each side of me. "Where you going?"

"I'm going to a friend's house," I said.

"Got a long way to go?" he asked.

"Not too far, I don't think," I said.

He put his hands on my handlebars, near my own hands. I kept my eyes on his, but kept the other guy in my peripheral vision. I was tense, but stayed motionless and expressionless. He looked at me for a second, then took his hands away.

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"You be careful now," he said. "There are some rough people out there."

Greatly relieved, I biked the rest of the way to my destination for the day and spent a peaceful night indoors. I had expected hazards along the way, but it had not occurred to me that I might meet would-be robbers.

Mid-Hudson Bridge

Mid-Hudson Bridge

Pedaling Across New York

I knew I had to get across the Hudson River and I was not sure where I was going to do it. I went to Poughkeepsie, but the bridge there was too serious - no pedestrians, bicycles, horses, etc. allowed - so I headed north to Hyde Park, where I found Franklin D. Roosevelt's mansion and a very nice state campground overlooking the river.

In the morning, as I continued north, I could see the Catskill Mountains looming on my left, an immense green expanse. Looking at my map, I saw a space between the Catskills and the Adirondacks and aimed for that. I did not want to bike through Albany, so resolved to cross the river just south of there. Unfortunately there were no bikes allowed on that bridge either, so I disassembled my bike and hitched a ride. Eventually a guy in a Chevy Vega gave me a lift over the bridge.

Continuing through towns like Paris and Rome, the hills were three miles up and three miles down. I passed a guy on a mountain bike on his three-mile commute home from work. His pace was about twice as fast as mine in my lowest gear. It took me about two miles to catch him. We talked briefly. He was amazed I had biked from Boston. Along the road I occasionally stopped at farm stands and bought fresh vegetables to go with my dried food. I made my campground connections every time without incident. The weather continued to be dry.

I biked past the Iroquois Wildlife Refuge where otters played in pools beside the road. In Syracuse I stopped to photograph my bike leaned against a monument and somebody stole my backpack. No clean clothes for me! Oh, well. In Fayetteville a blonde in a Cadillac convertible ran me off the road. I executed a perfect somersault over the handlebars and stuck the landing. I would have given myself a 9.3. She kept driving and I kept biking. I guess no harm done. As I neared the western part of the state I ran into a couple of days of rain. I checked into a motel to dry off and continued my journey after a couple of days of daytime TV.

Near Spring Brook, New York, I met a couple that had biked from Ohio. The skin was peeling off the man's face. They were happy to see another bicyclist. They were headed to Nova Scotia. I remember thinking they were crazy, and then thinking, well, they're no crazier than me. At last I rolled into Buffalo, completing my 400 mile journey across the Empire State. I was totally out of money, but I still had food.

My last bike?

My last bike?


Once over the bridge into Niagara Falls, Ontario, I found a campground for the night. It was one of the few campgrounds that offered a shower and I was glad. After I got used to the constant noise of the falls, some three miles distant, I slept well.

On the map I saw very limited choices to get across Ontario. There was the freeway and a highway. The only choice was the highway. A freeway is no place for a bicycle. Unfortunately, what I didn't know was that the freeway was a toll road with hefty tolls for truckers, and all the heavy trucks took the two lane highway. The shoulder was soft gravel and no good for my overloaded road bike. I got blown off the road six times that first morning and gave up. Once again I disassembled my bike and stuck my thumb out. A guy in an Astre - the Pontiac version of the Chevy Vega hatchback - picked me up and drove me across Ontario.


I took the ferry boat over to Michigan across a narrow channel on Lake Huron.

The American border guard gave me a lot more trouble than the Canadian border guard had. I really thought he was not going to let me back in. All I had was my Wisconsin drivers license. He wanted a birth certificate or a passport or some such. In the end, however, he let me back into my homeland.

Between Lake Huron and Lake Michigan, the state of Michigan is totally flat. Running low on food and money, I had to make good time, and I did. Daily centuries - 100 mile stints - for three straight days took me across the state. I camped in very nice lakefront campgrounds in Cadillac and Bay City. There was a beautiful sunset at Cadillac. Just north of Frankfort I had a flat - the only flat tire of the trip. I fixed it in time to make the ferry across Lake Michigan to Wisconsin. I had just enough money for the fare.


A storm came up as I was boarding the ferry. I secured my bike with a bungie cord to an outer bulkhead on the car deck and took a seat in the cabin. There was thunder, lightning, and driving rain as the boat pounded its way through six foot rollers across the lake for four hours. I was glad when we finally docked.

In Keewanee, Wisconsin, it was getting dark and I was exhausted. I found a park by the waterfront and rolled my sleeping bag in the tarp by the edge of some trees and went to sleep. It was a chilly night. Surprisingly I slept past dawn and was awakened by some locals who came down to launch a boat. They were surprised to see me.

I packed up and rode the last thirty miles or so to Green Bay, where I looked up an old roommate from college and stayed with him. So ended my trip.

It was a great adventure for a young man. I don't think I'd attempt it now.


Trip Statistics

  • Total elapsed days: 21
  • Days on the road: 17
  • Total miles: about 1000
  • Daily average miles: about 68
  • Longest mileage in a day: 103 miles
  • Shortest mileage in a day: 3

The bike: Sekine 10-speed, chrome-moly frame, Suntour V derailleur, Diacompe brakes.

Other equipment: Cannondale front and rear panniers and two handlebar bags.


Tom rubenoff (author) from United States on March 05, 2009:

Have a great time, Funride.

Remembering the Wisconsin ride has got me over a lot of hills. All I'm doing now is cross training, but I'll get the winter bike out again next week. I have a 175-mile event coming up end of June. I am hoping to increase my speed!

Ricardo Nunes from Portugal on March 05, 2009:

Hey Tom, what a great adventure hub. Thanks for sharing, I enjoyed riding with you while reading this inspiring hub. I wish I had 22 again and all the time needed to go for a big ride like this... nowadays I am happy if I can ride an entire weekend. This next weekend I´ll attend a 24hours competition and I will enjoy every moment riding.

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