Berkshire Big Adventure Dual Sport Ride

On Saturday afternoon with our tent and sleeping bags packed, Kenny and I hopped on the ferry to cross the Long Island Sound. We headed towards Winsted, Connecticut to the White Pines Campground. Sunday morning we would be joining the LI ADV gang on the Berkshire Big Adventure dual sport ride. It is an annual charity event held by the Berkshire Trailriders Association.

We arrived at the camp to find 80% of the gang already there and suiting up to head out for a ride. We said our “hellos” and watched them as they rode away to get dirty. In the meantime, Kenny and I unloaded our stuff and set up camp.

Berkshire Dual Sport Ride

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As a few more stragglers arrived we decided to take a road ride around to see a little bit of the area. In reality we really went to get beer but just happened to take the long way around. We arrived back at camp to find a BBQ in full swing and spent the remainder of the evening laughing, sitting by the campfire and just enjoying being outdoors. It was a great night.

On Sunday morning we headed off to Tuckers Pub in Sandisfield for the ride sign-in where there was already a good crowd of bikes assembled.

The ride was listed as a big bike friendly dual sport ride. It was a mixture of some paved roads, dirt roads and unmaintained woods roads. There were also 5 hero sections available to riders who were looking for something a bit more challenging. I avoided those altogether, even the one marked as ‘easy’  near the end of the route. Everyone told me that it was no more challenging than some of the regular route sections when I met them on the other side. I guess I was completely put off by the fact that it was tagged as a hero section. My biggest hurdle is apparently my lack of confidence, not so much my lack of riding ability.

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Kenny is officially my hero

Initially I was going on this ride alone but at the last minute Kenny was able to come along on the big bomber GS, which is fitted with regular street tires. Between the two of us having little and  no experience riding offroad we didn’t know what to expect from the route. My brain imagined something like hard-packed dirt roads. Neither he nor I imagined ruts, golf ball sized gravel and wet rocks. I’ll chalk this up to both of us being noobs.

It was Kenny’s first time riding offroad. He bravely navigated that big, heavy beast through everything that came his way. Sure there was some cursing and a few scary moments but he clearly has a skill that I was unaware of. I would have cried and packed it in at the first sight of a rocky uphill climb. But, he didn’t. He soldiered on and I’m really proud of him. I see a dirt bike in his future.

Light at the End of the Tunnel

Up to this point any of my wimpy tip-toeing through the dirt had been a scary and frustrating exercise. Everything changed during this ride. I don’t know if I was just in a better mindset being with people that I know and trust or if I was finally mentally ready to just hand myself over to the process a little more.

Thank You Come Again - Fuzzygalore Motorcycle BlogI felt great all through the ride. I worked at keeping my speed up and my eyes looking further ahead. Both of these things helped tremendously. I was able to stay with the group and wasn’t gripped by fear. That’s a new sensation for me on something other than tar. In retrospect, I feel like it was the speed that helped most.

I came away from this ride feeling excited and very much looking forward to next time!


Rachael is the whimsical writer behind the 20+ year old Girlie Motorcycle Blog. As a freelance blogger, she is on a mission to inspire laughter, self-examination, curiosity, and human connection. Girlie Motorcycle Blog can be found on several Best Motorcycle Blog lists.

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14 Responses

  1. Pimmie says:

    Congrats to the both of you! Hope you two wont wonder of on any trail rides in Italy… 😉

  2. OG says:

    Must have been the week for getting down on two wheels! Congrats on a fun ride. A plated dirt bike certainly opens up a new world to enjoy 🙂

    • Fuzzygalore says:

      It was really super fun.

      It also introduced you to places and areas that you wouldn’t normally see on paved roads. some very beautiful natural settings. There were about a million things I saw I wished I could stop and take pictures of – which I didn’t do.

  3. Crudmop says:

    We need to go back up and do that route again 🙂

  4. Pimmie says:

    Better run and hide K…. 😉

  5. Pimmie says:

    Ok, better rund and hide F… 😉

  6. Digger says:

    Thanks for coming out and riding our event. We really try to cater this ride to anyone who shows up, which is a hard thing to do considering different riding abilities, not to mention all the various types of bikes. I just wish you kept up that courage for the last section. In hindsight, it wasn’t any more difficult than a thing or two in the middle.

    • Fuzzygalore says:

      Hiya Digger-
      I really did have a great time. I can’t imagine how hard it must be to please everyone but you seemed to do a great job of it. 🙂

      I wish I did the easy hero, too. I feel like i wimped out but c’est la vie. I look forward to the time when my confidence lets me do more.

  7. Deker9 says:

    My cheezypoofs mysteriously disappeared in this version of the pictures 😉

  8. Trailrider says:

    Cool report.

    I agree that in Dual Sport biking you see places and areas that you wouldn’t normally see on paved roads.

    Hope to read many more reports like these.

    Regards from Sunny South Africa


  1. May 26, 2010

    […] This post was mentioned on Twitter by Two Wheels Down, Motorcycle Stuff. Motorcycle Stuff said: FuzzyGalore: Berkshire Big Adventure Dual Sport Ride Full […]

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