A Boston Tailwind

When you think of a windy city you probably think of Chicago first. But in actuality Boston is the REAL windy city. And all the cyclists here know that.

They also know that no matter which direction you bike in the wind will be in your face.

Tailwinds are not entirely impossible in Boston, they’re just very rare. But if you ever get one it will give you a new perspective…


A Boston Tailwind


And maybe even be a bit magical…


A Boston Tailwind


After which it will drop you in your favorite bar with your favorite friends and your favorite drink.


A Boston Tailwind


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  • Tips January 18, 2012   Reply →

    Whew. I thought a boston tailwind might be some sort of Guinness-powered flatulence!

  • cycler January 18, 2012   Reply →

    I haven’t met one yet, but I’m hoping it will take me over fenway now!

  • cris January 18, 2012   Reply →

    I have met the occasional Boston tailwind, and it’s been fantastic, but sometimes shortlived, especially if crossing over a bridge hands me over to a Cambridge headwind.

  • Dave January 18, 2012   Reply →

    Portland tailwinds are kind of like that too – one of the few times I caught one, I was luckily going up a hill, and it lifted me and my 45lb bike right up it. I spend a lot more time though on flat ground, barely moving forward, with my cheeks flapping in the wind :)

  • GRJim January 18, 2012   Reply →

    This has me curious – Boston is on the water so windy, but what causes the swirling?

    • Matt the Scruffy Mechanic January 18, 2012  

      the beer, Jim. The wind is blowing straight, it’s just heads that are spinning

    • GRJiim January 19, 2012  

      Clearly, Matt. You’d have to be drunk to be a Bosox fan. Ba-dum!

    • Matt the Scruffy Mechanic January 19, 2012  

      I was tactfully not pointing that out, as I figured some of the readership might take offense at having someone as geographically fortunate as myself say so.

  • Richard Masoner January 18, 2012   Reply →

    Is there a gadget I can buy to convert headwinds to tailwinds?

    I love the site redesign.

    • Matt the Scruffy Mechanic January 19, 2012  

      A standard headset will do it, you just turn around and go the other way! Unfortunately this may result in having to go some 20-odd-thousand miles out of your way to get a coffee, but think of the epic ride report you could post when you got home!

  • Loving the Bike January 19, 2012   Reply →

    If there isn’t one yet, I’ll bet Richard can develop a gadget to turn headwinds into tailwinds….and I’m ready to invest in that company.

    Great site you’ve got here, Bikeyface.


  • Tyler January 19, 2012   Reply →

    I wasn’t on a bike, but I had a rare tailwind on the way to the T the other day. Usually when there’s wind strong enough to fight for control over where I’m going, it’s a blistering attack from the side or worse, a veritable hurricane-force assault from the front. A wind at my back strong enough to take over forward propulsion from my leg muscles was unheard of!

  • AJ January 21, 2012   Reply →

    And though we all know this to be true, I always see that guy on his windskating board at Critical Mass. And the damn thing’s always in his face. One day, he’ll make it up the hill, and it’ll be glorious.

  • Skip Tooth June 6, 2012   Reply →

    A famous quote from my mother’s letters (y’know, in my family) says “No matter which direction you go in Boston, the wind is always in your face.”

    I’m not sure why the period goes inside the quotation mark but that is another thing entirely.

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