On Biking: 50 miles on the Tour de Boston

By Jonathan Simmons, Guest Columnist

Late last fall my friend Lane and I decided to ride all of Boston’s 50-plus miles of bike lanes in a day. A 50-mile ride is something we could typically knock off in about 2 ½ hours. Boston is pretty flat, so we figured this would be a leisurely stroll.

Boy did we figure wrong.

Nicole Freedman, the Boston bike czar (at least until April 20th), sent me a map of the city's bike lanes. I’m no cartographer, but even I could see that our route was not contiguous.

This ride was going to be a little more complicated than I had originally thought. Also a little longer than 50 miles. Still, worst-case scenario, I figured we could do a modified route over the course of a day.

Even then, I underestimated our challenge by a factor of two.

We began our Tour de Boston (TdB) at 8 a.m. on a Sunday morning in Kenmore Square and headed west on Beacon Street. The cobblestones along the reservoir near Boston College made it feel like we were racing in Paris-Roubaix (otherwise known as the Hell of the North), the toughest one day race on the pro calendar.

My favorite sign on our TdB read, “Bicycles may take the full lane.” My second favorite sign was on the ground near the crosswalks along Commonwealth Avenue near Boston University. It instructed pedestrians to look left for cyclists before crossing the street. I know that won’t stop jay-walkers from darting out into traffic, but perhaps it will slow them down enough to avoid an accident.

As we rode across the Rutherford Avenue Bridge and looked down through the metal grate we could see the reflections from above bouncing off of the water down below. One more thing you miss when you’re trapped inside of your car.

We decided to ride to the Bunker Hill Monument. I’m here to report that hill is quite steep. Fortunately it is also quite short. By then it had warmed up enough for us to take off our ear warmers.

We took the water ferry across the harbor to East Boston. I almost convinced myself that I was on a cruise ship. Unfortunately, we docked at Logan airport. The roads around Logan are bad enough in a car. On a bike they’re a disaster. At one point I tried to hail a cab, moments before we almost pedaled down the ramp for the Ted Williams Tunnel. Fortunately we found the Blue Line, which we rode to Maverick Square.

From there we pedaled past Paris, London and Liverpool (the names of local streets), abandoned factories, and a strange set of concrete pilings on an abandoned Massport lot that looked like something you’d see at Easter Island.

In Maverick Square, I realized I was hungry. Actually, I was starving (bonked is the term cyclists use). The smell of fried food coming from McDonald's was so inviting that even I, a vegetarian, almost ordered a Big Mac.

By then, Lane and I realized that we were both too spent to ride another 30 miles. In fact, we were both too spent to figure out where to eat. Instead we rode along the Esplanade and headed back to Brookline. We wisely agreed to complete our TdB another day.

Once I got home I did the usual biker thing: I ate, I napped, and I showered. Sadly, in that order. I was too tired to do otherwise.

A little more than a month later we decided to head out again for part two of our TdB, though by now we knew that we would not be able to ride all of Boston’s bike lanes.

For the first part of the second stage of the TdB we were lucky to have Nicole Freedman join us. Nicole is a former Olympic cyclist and one of the nicest people I could imagine riding with. She’s smart, too. I bet Nicole could have figured out how to get around the maze of roads that surround Logan.

Nicole has done much to make Boston a more inviting place to ride. Still, there were some neighborhoods where we were not greeted with open arms. Like the guy who gave us the two handed bird for reasons I still can’t figure out as we sprinted past.

After two days of riding I was struck by the fact that we had only scratched the surface of what’s out there to see around town. We had skipped past farms, trucks selling cupcakes, and many of Boston’s bike lanes.

Our TdB was not fast and honestly, we didn’t ride that far. And yet it was fun. That’s how it is when you’re cycling. Even on a cold and windy day, a spin on your bike is sure to bring a smile to your face.

Jonathan Simmons is a psychologist and an avid cyclist. His book, “Here For the Ride” will be published later this year.